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44 Islands and 42 Bridges: A Florida Keys Road Trip

It’s only 113 miles from Key Largo to Key West, but take it slow and savor the subtropical, sometimes kitschy, flavor, of these fragile isles.

A street performer entertains his audience on Mallory Square in Key West, Fla. Credit... Scott McIntyre for The New York Times

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By Elaine Glusac

• Dec. 17, 2018

Seagulls and squadrons of brown pelicans flew alongside my rented Hyundai as I drove across the astonishing seven-mile stretch of U.S. Highway 1 that runs across Moser Sound, just south of Marathon, in the Florida Keys. The proximity of birds and water blurred the distinctions between sea and sky, drive and flight.

The string of coral islands that arc from the Florida peninsula south toward Havana has a long history of attracting pirates, profiteers and seekers of a Caribbean lifestyle within the United States. Henry Flagler, an early developer of the Florida Keys, inadvertently gave the country one of its most scenic roadways when his Overseas Railway, running from mainland Florida down to Key West, was destroyed in a 1935 hurricane. That land route eventually became the Overseas Highway, or U.S. 1, vaulting across channels, and linking 44 islands, via 42 bridges.

I first drove the route with my sister in the early 1990s with a beer-filled cooler, tanning ambitions and the kind of dropout, sunbaked attitude that still drives the party crowd to the Keys, particularly Key West. The distractions along the way haven’t changed much. Local police and sheriff’s vehicles are still parked on the sides of the highway, jittery reminders that speed limits are strictly enforced. Cyclists share narrow shoulders over the 113-mile route from Key Largo to Key West. Manatee-shaped mailboxes, fishing marinas and seafood shacks proliferate. But most distracting are the views themselves, with the sparkling Atlantic to the left and the aquamarine Gulf of Mexico to the right as the road skips across scores of breezy, swim-inviting straits.

Gulf of Mexico

Upper Matecumbe Key

detail below

Atlantic Ocean

1. Dagny Johnson Key Largo Hammock Botanical State Park

2. John Pennekamp Coral Reef State Park

3. Fish House

4. Bungalows Key Largo

5. Playa Largo Resort & Spa

6. Robbie’s

7. Indian Key Historic State Park

8. Alligator Tree Lighthouse

9. Curry Hammock State Park

10. Dolphin Research Center

11. Bahia Honda State Park

12. Big Pine Kayak Adventures

13. National Key Deer Refuge

14. Matt’s Stock Island Kitchen & Bar

Over the course of repeated trips, I’ve come to appreciate the nature and wildlife of the Keys, home to endangered Key deer, mangrove forests and the only living barrier reef off the continental United States.

Hurricane Irma, which struck in September 2017 with Category-4 fury, threatened the delicate balance by which so many humans and animals exist amid the mangroves and bays. In November — 14 months and much cleanup later — I drove the route to assess the scars as well as the renewal, from recently opened (or about to open) resorts to a new coterie of mermaids.

Below is a guide to this classic coastal road trip. You could drive it in a single afternoon, but you won’t want to. Three languid days is more like it.

From the rental car center at Miami International Airport, it’s just over an hour’s drive on mostly suburban highways to the Everglades bogs that edge Key Largo, the northernmost Key and the first to introduce visitors to both the natural attractions of the islands and Keys kitsch. At Dagny Johnson Key Largo Hammock Botanical State Park , I stretched my legs in a native hardwood forest alongside bird-watchers who could identify a palm warbler just by its call, before hitting the bustling Fish House restaurant trimmed in strings of tiki- and flamingo-shaped lights.

Its proximity to Miami has made 18-mile-long Key Largo — a place where thick foliage obscures the water from the T-shirt and shell shops — attractive to developers eager to lure those who may not want to drive any farther down the highway.

“South Florida traffic is our bread and butter year-round,” said Herbert Spiegel, a consultant for the new Bungalows Key Largo , as he guided a tour of one of the island’s newest resorts, with its fleet of electric boats, a Himalayan salt room in the spa, four restaurants and bars, and an adults-only policy. “Florida is all about kids,” he added. “This is something different.” (And it doesn’t come cheap: all-inclusive rates at the resort, which opens this month, start at $1,300 per night, per couple).

Like the nearby Playa Largo Resort & Spa , the 135-cottage resort replaces a former R.V. campground, a trend that is nudging Key Largo upscale. But as the first stop nearest to the reef, it still attracts divers and ocean lovers across the economic spectrum to John Pennekamp Coral Reef State Park , where snorkeling tours explore the vibrant corals and the tropical fish they support in 70-square-miles of protected waters.

The everyday — in the form of schools, grocery stores and one very large Starbucks — mingled with signs for bird sanctuaries and state parks over the next 20 tropical miles from Key Largo to Islamorada. Spread across six lush islands, the community has an old-money heritage and a reputation as the sport fishing capital of the Keys, both of which came together in the bonefishing tournament that the late President George H.W. Bush ran for a decade from Cheeca Lodge & Spa , a vintage property with roots that go back to 1946. It’s no wonder the recent Netflix series “Bloodline,” a dark story built around a prominent Keys family, was based in affluent Islamorada.

Keys History &

Discovery Center

Lodge & Spa

Pierre’s

Morada Bay Beach Cafe

Midway Cafe & Coffee Bar

Pines and Palms Resort

The fictional Rayburn House inn from that series is the actual Blue Charlotte villa at the Moorings Village , where 18 rental cottages, some dating back to the mid-1930s, occupy a former coconut plantation. The hurricane denuded the property and killed its signature palm tree that bowed over the water.

“Not a blade of grass was left,” said Debbie Pribyl, the general manager of the Moorings, where the cottages have all been reroofed and the landscaping replanted. On this November day, three fashion photography crews were using the beach as a backdrop. “We got more sand than we started with.”

That ocean-side beach is private, but the two restaurants that the resort runs on the Gulf side aren’t. The casual Morada Bay Beach Cafe and the more refined Pierre’s draw nightly sunset crowds to tables set in the sand near speakers disguised to look like coral rocks emitting samba music as twilight paddleboarders stroke by.

Modest roadside inns, including the newly rebuilt Pines & Palms Resort with apartment-like rooms, eclectic restaurants like Midway Café and an arts district with a brewery and galleries contribute to Islamorada’s bohemian character. A new self-guided tour available via a free cellphone app from the history museum Florida Keys History & Discovery Center introduces hurricanes, pirates and island pioneers, winding up back at Cheeca Lodge where many of these original “Conchs” were buried.

To delve deepest into Keys history, Brad Bertelli, the curator of the Florida Keys History & Discovery Center told me, travelers have to leave the road at Islamorada, and become waterborne.

He and I launched rental kayaks from Robbie’s marina in Islamorada, a popular stop for feeding tarpon the size of teenagers, and headed for the offshore Indian Key Historic State Park . The 11-acre, mangrove-fringed island, with a shady tamarind grove and spiky sisal plants bordering the paths, holds the remains of a 19th-century wrecking village devoted to salvaging goods from ships that ran aground on the reef.

I n the 1830s, Indian Key was the seat of Dade County, site of a bowling alley and an inn promising “one of the most favorable situations in the United States for persons who are suffering from pulmonary, dyspeptic and numerous chronic diseases, and obliged to seek refuge from the chill blasts of a northern winter,” according to a sign posted on the site. Prominent Keys travelers, including the ornithologist John James Audubon, passed through.

“Wreckers were thought of as the pirates of the day,” said Mr. Bertelli, looking the part with a bandana tied around his head. “Like used car salesmen, there were some bad apples.”

Today, the ghost of its town square is a large field surrounded by rock foundations of storehouses, cisterns and homes, eventually abandoned after the Second Seminole War in 1842. A three-story observation tower offers views to distant Alligator Lighthouse, marking the reef where the wreckers plied their trade , and, in the opposite direction, Lower Matacumbe Key, the source of fresh water, which allowed the island to flourish.

Middle Keys

Another 30 miles south, past innumerable cormorants perching on power lines, and you enter another world. Lobster traps line the street to Keys Fisheries in Marathon, a commercial marina harboring fishing boats and pleasure sailboats, and a dockside restaurant where baby nurse sharks school in the shallows, waiting for scraps. The restaurant is an apt introduction to the working heartland of the Keys. Here, locals and those just passing through put in orders for lobster Reubens under superhero pseudonyms and wait to hear, “Captain Marvel, your order is ready.”

Commerce mingles with conservation in Marathon, home to two nonprofit marine attractions, the Dolphin Research Center and the Turtle Hospital . Both fund their operations largely through visitor tours.

Keys Fisheries

AquaVentures

Beach Resort

Housed in a former motel painted sea green, the Turtle Hospital treats animals that are rehabilitating after swallowing so much plastic they can’t submerge, or have tumors growing around their eyes, a condition linked to water quality. Visitors see the operating room, the research lab and tanks filled with turtles ranging from hatchlings to 300-pound adults.

“It’s a very exciting time to be in sea turtle medicine,” said Bette Zirkelbach, the energetic manager of the Turtle Hospital on a tour, as she described a pioneering study in the lab on blood turtle types.

Nature-based tourism isn’t new to the Keys — snorkeling, diving and bird-watching are popular throughout the islands and, as I drove, a radio news broadcast urged listeners to use the “I Spy a Manatee” mobile app to both identify the animals’ locations and encourage safe boating around the slow-moving creatures. But getting travelers out of motorized fishing boats and into kayaks is relatively new on Marathon, where Miranda Murphy and Steve Tomek run three-year-old AquaVentures , which offers guided kayak tours in the tangled mangrove channels at Curry Hammock State Park.

As a naturalist, Ms. Murphy treats the waterways like living aquariums, pointing out schools of baby snapper and using a net to pull up starfish and jellyfish that illustrate the role of mangroves as nurseries of the sea. “It’s like a touch tank in the wild,” she said.

In March, AquaVentures will move its base of operations to the new 24-acre Isla Bella Beach Resort . Kayak tours of the mangrove tunnels in nearby Boot Key will take off from a canal at the resort where, on my visit, six manatees spent hours in the warm shallows.

Bahia Honda

Seven Mile Bridge is the largest span in the Keys, and so exhilarating to cross that I returned another day to experience the drive in the blush light of dawn. It separates the Middle from the Lower Keys, and more commercial islands from some less developed ones, beginning with Bahia Honda Key, home to Bahia Honda State Park .

Beheaded palm trees and white sand beaches shorn of their shady sea grape trees testify to Bahia Honda’s location near the eye of Irma. This fall, one of its beaches reopened and snorkelers were trolling the shallows, but its popular Sandspur Beach, once lined with sea grapes decorated by visitors in seashells and driftwood, remains closed. Still, from the top of the old Bahia Honda Bridge, part of the original railway, there are hypnotic views across a 30-foot-deep channel that represented one of the most challenging to track-builders, sometimes limited by the tides to two 45-minute shifts a day.

Big Pine Key

Six miles west, much of Big Pine Key and neighboring No Name Key comprise the National Key Deer Refuge established in 1957 to protect the dwarf Key deer, an endangered subspecies of the North American white-tailed deer that grows just three feet tall. At the refuge visitors’ center, in a strip mall where a pair of free-ranging roosters foraged the parking lot, volunteers told tales of deer showing up beside a Winn Dixie grocery store dumpster, and extolled the resilience of the herd, which is now estimated to have between 500 and 800 deer. Many of the mangrove areas that edge their habitat remain barren after Irma.

Here, I met Bill Keogh, the easygoing owner of Big Pine Kayak Adventures , who guides paddling trips from Big Pine Key to the “backcountry,” a largely protected region of undeveloped mangrove islands. He still sees baby stingrays, snappers and sharks and, post-storm, a preponderance of lobsters on mangrove island fragments dispersed by the hurricane . “It’s the same biomass out there,” he said, “but it’s concentrated in new real estate.”

Leaving him at sunset, I crossed a bridge to No Name Key to look for deer, which I found not only there — collie-sized critters galloping across the sandy road — but, on my return to the highway, where I stopped to watch an elfin stag, doe and fawn grazing a town lawn.

Stock Island

After 25 quiet miles crossing calm bays with views to distant patches of mangrove isles, I reached the outskirts of the city of Key West on Stock Island, a traditionally blue-collar refuge for shrimpers, commercial fishermen and tourism industry employees. With its mobile homes and canals moored with houseboats, it retains a grittiness that its more manicured neighbor, the island of Key West, has largely lost. But it, too, is experiencing development, now mingling marinas, newly paved streets and bushy bougainvillea with a pair of new resorts including the Perry Hotel Key West .

With art installations made of propellers, the 100-room hotel facing a recreational marina nods to the shrimp-trawling boats across the channel. Its main restaurant, Matt’s Stock Island Kitchen & Bar, has become a dining destination for upscale versions of local seafood, such as black grouper with cornbread gnudi and crawfish-thyme butter, recommended by my Russian waitress who said she came to the Keys on vacation and has stayed seven years.

“The islands got me,” she laughed.

The next day, the Perry’s free 15-minute shuttle dropped me in teeming downtown, tourist-thronged Key West, the end of U.S. 1 and home to harbor-front bars and souvenir shops with a prevalence of mermaid ornaments, statues and paintings. In this setting, the Captain’s Mermaid boutique owned by Kristiann Mills, a native Conch who identifies as a mermaid, is a tranquil, if glittery, refuge. She explained that many of her mermaid “pod” teach “mermaiding,” or swimming in a long tailfin , and that she is launching the first Key West Mermaid Festival , July 5 to 7, to draw attention to conservation.

“We’re a little angry the ocean’s being polluted and we’re coming on land to tell you about it,” said Ms. Mills, with the warm smile and flowing hair you might expect of a mermaid.

Home of the Conch Republic, which tried to secede from the union in 1982, Key West has long attracted nonconformists, artists and especially writers, from Ernest Hemingway — whose former house-turned-museum is famously filled with descendants of his six-toed cat Snow White — to Judy Blume, who co-founded Books & Books @ the Studios of Key West , a bookstore within a nonprofit gallery just blocks from the bar-lined Duval Street.

“Duval is a tiny Bourbon Street,” said Shannon McRae, the general manager of Key West Food Tours , over a Hemingway daiquiri off Duval on her company’s new Craft Cocktail Crawl. The three-hour tour visits dives as well as chic lounges. “We want to surprise you and let you drink like a local.”

Key West, a village of tidy bungalows and Victorian captain’s homes, offers much more than bars, of course, and it isn’t hard to escape the rowdies on neighborhood walks or in attractions like the Key West Butterfly & Nature Conservatory , a calming sanctuary of blue morphos, pointed leafwings and dusky swallowtails.

Books & Books

@ The Studios

of Key West

Captain’s

Mermaid Boutique

Ernest Hemingway Home and Museum

Key West Butterfly &

Nature Conservatory

Southernmost Point

of the Continental U.S.

Around the corner, selfie-takers lined up at an oversize buoy marking the Southernmost Point of the continental United States, painted with an arrow indicating “90 miles to Cuba.” Many came from cruise ships to get their Instagram shot. Cruise traffic is growing on Key West, where 405 calls are expected in 2019 versus 307 in 2016.

Many ships sail out before sunset, which is a shame as sundown cues a carnivalesque celebration nightly at seafront Mallory Square that’s both a tribute to nature and a showcase for quirky characters who make their living in Key West. At one end of the seafront strip, I watched a ringmaster run house cats through hoops like circus felines ; on the other end a contortionist quipped, in the outsider’s humor so common to the Keys, “I call this an economic recovery. It’s an illusion.”

Elaine Glusac is a frequent contributor to the Travel section.

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An Exciting Trip to Key West, Florida Essay

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Key West is one of the most fabulous places in the world. I would recommend to everyone who enjoys traveling to visit this place and enjoy its beauty. Key West is a city and also an island of the same name near the southernmost tip of the Florida Keys in Monroe County, Florida, United States. Travelers can reach this exotic place either through the seaport or by air. The Key West International Airport provides airline service. Hotels and guest houses are available for lodging.

Besides, people who enjoy food are not left behind; there are several restaurants that offer a variety of indoor or outdoor dining. The most attracting tourist spots in Key West is the fabulous Key West sunset, the enchanting walk through one of the Old Town lane and the smell the jasmine, or even enjoying the popular duo at one of the bars on Duval Street can be a some of the most memorable moments in one’s life.

Generally, the most unique structures in Key West date from 1886 to 1912. The most unique features that differentiate the local architecture include wood frame construction of one to two-and-a-half story structures set on foundation piers about three feet above the ground. Exterior characteristics of the buildings are peaked “tin” roofs, horizontal wood siding, pastel shades of paint, side-hinged louvered shutters, covered porches (or balconies, galleries, or verandas) together with the fronts of the structures, and wood lattice screens covering the area elevated by the piers. For any of the tourists, these are some of the unique features that can inspire them. The new section on the east which is perceived as north is now called “New Town.” This place contains several shopping centers, strip malls, and the island’s commercial airport.

It can be said that each and every person starting from the young to the old ones have some attractions for them. There are some of the finest saltwater fishing are people enjoy these activities. Besides, the fresh seafood dinner at one of the fine Key West restaurants is another delicious treat. Tourists can also enjoy a trip on a smaller charter to view dolphins in the wild or to kayak in the backcountry off Key West.

One of the biggest attractions on the island is a concrete replica of a buoy at the corner of South and Whitehead Streets that is said to be the southernmost point in the adjacent 48 states. This point was initially just marked with a sign, which was often stolen. As a result, the city of Key West erected the now famous monument in 1983 (Key West History). Brightly painted and labeled “SOUTHERNMOST POINT CONTINENTAL U.S.A.”, and it is one of the most visited and photographed attractions in Key West (AOL city guide).

It is often seen that many visitors rent a bicycle and explore the history and architecture of Old Town Key West. Additionally, there are also walking tours, together with a tour of the unusual Key West Cemetery. The Sunset Celebration at Mallory Square is an everyday attraction for visitors and residents. Most people whether young or old enjoy Key West and also there are many who continue to visit this place. Boat excursions and tours provide a great way to view Key West from the water. I would like to recommend Key West, Florida to everyone who enjoys traveling. This is one of the most exotic places in the world and has several unique features.

AOL cityguide. Southernmost Point. 2007. Web.

Key West History, Key West Vacation Rentals, (2006). Web.

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12 reasons to visit Key West, Florida

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Once a rip-roaring buccaneers’ town, Key West is now the quirky, tropical heart of the  Florida Keys . Closer to Cuba than mainland Florida, visiting Key West feels a million miles from the rest of the USA . The island’s boisterous history, free-spirited outlook and unique “Floribbean” vibe are powerful draws for all kinds of visitors, whether you’re into water-sports, night-life, nature, or art. Here are our twelve top reasons to visit Key West.

1. Awesome aquatics

2. bahama village, 3. sunsets worth celebrating, 4. duval street drinks, 5. hemingway’s home, 6. key lime pie, 7. maritime marvels, 8. charming old town architecture, 9. cuban culture, 10. birds and butterflies, 11. african cemetery, 12. smathers beach, key west in brief.

The entire Florida Keys is an ocean-lover's paradise, with a host of unforgettable water-based activities and experiences to enjoy . So, whether you’re an experienced diver or novice snorkeller, oceanic activities should figure high on your to-do list when visiting Key West.

Head to the historic Seaport to take your pick from several longstanding operators offering everything from wreck dives, reef dives and mangrove kayaking, to glass bottom boat trips. To make the most of Key West's watery wonders, you could book a "double dip trip" . With stops at two top snorkelling sites reached on a high-speed state-of-the-art catamaran, this provides fun and thrills aplenty.

Fancy fishing Key West’s stunning waters? Check-out  Andy Griffiths Charters .  An experienced local fisherman, Andy can arrange epic three-day excursions out to the Dry Tortugas or, for a less full-on (and more affordable) experience, you could try the four-hour fishing option.

For excellent onsite watersports, you could investigate booking a stay at Parrot Key Hotel and Villas . One of the most luxurious resorts in town, it's lushly-landscaped and set on a white-sand beach, with four swimming pools and close proximity to Old Town.

Florida coral reef © John Pennekamp/Shutterstock

To soak up the old-time atmosphere of Key West, visit the narrow streets around the lighthouse and to the west of Whitehead Street - aka Bahama Village. Many of the small buildings - some of them former cigar factories - are pretty run-down and provide a contrast to the restoration found elsewhere in Old Town. The Caribbean vibe here is authentic, deriving from the Bahamians who worked in the salvage trade and eventually settled in Key West.

Key West's Bahama Village © travelview/Shutterstock

Taking time out to take-in an epic sunset (or several) is an absolute must when visiting Key West. And, thanks to the daily Sunset Celebration - started by hippies in the 1960s, and now managed by the Key West Cultural Preservation Society - you can enjoy this exceptional solar spectacle in the company of jubilant jugglers, flamboyant fire-eaters and fellow revellers. The celebrations kick off two hours before sunset on bustling Mallory Square, with plenty of food stalls, cocktail stands and craft vendors adding to the distinctly Key West vibe.

For a more serene sunset-watching experience, you could take to the seas on a schooner and book a two-hour sunset sail that also offers opportunities to see dolphins, sea turtles and water birds as you sit back and sip sun-downers.

Typical Florida sunset © Shutterstock

Many of Key West’s best nightlife joints are centred around Duval Street, which is home to a host of bouncing bars enjoyed by everyone from ageing rockers to students. Try the Green Parrot for live music, where locals dance and drink until the early hours.  Sloppy Joe's  is another popular spot but, despite what you may hear (it's a much-debated topic), its original location (now Captain Tony’s Saloon) was the bar frequented by Ernest Hemingway.

Sloppy Joe's on Duval Street

Related articles from the blog

Literature lovers visiting Key West would do well to check-out the  Ernest Hemingway Home and Museum , where this giant of American literature wrote some of his most acclaimed work. One of Key West’s grandest homes when it was built for a wealthy merchant in 1851, it was seriously run-down by the time Hemingway and his then wife bought it in 1931 (thanks to a gift from her wealthy uncle), though they soon spruced it up in luxurious style with the likes of a 60ft turquoise swimming pool carved from solid coral.

While visiting, be sure to keep an eye out for descendants of the writer’s famous six-toed cats.

Sampling Key lime pie is must-do when visiting Key West. This sweet-crusted dessert made from the citrus fruits every local seems to grow in their backyard is a tantalisingly tangy delight. While many places lay claim to having the best recipe, we recommend  Blue Heaven  for its distinctive take on this iconic dish - here slices are topped with colossal clouds of meringue in place of whipped cream. For a decadent portable version (frozen, served on a stick and slavered in chocolate), head to  Kermit’s Key West Key Lime Shoppe . 

Key West's iconic Key lime pie © Shutterstock

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With  family fun a feature of Florida  as a whole, Key West is no exception, and Greene Street’s  Mel Fisher Maritime Museum  definitely entertains and informs all ages. It's a fabulous way for kids to get up close to one-of-a-kind sixteenth and seventeenth-century galleons and their curious cargoes, including a stunning emerald cross, enormous cannons and a “poison cup” (reputed to neutralize toxins) that were salvaged from two seventeenth-century wrecks.

After years of searching, treasure hunter Mel Fisher discovered the Santa Margarita in 1980 and, five years later, the Nuestra Señora de Atocha. Both ships sank forty miles southeast of Key West during a hurricane in 1622 and yielded a haul that’s said to be worth at least $200 million. Monetary value aside (the Atocha alone contained 1041 silver bars and 77 gold bricks), the collection has huge historic importance, offering a window into the early years of Spanish colonization of America.

There’s also a sobering display dedicated to the slave ship Henrietta Marie, which sank in 1700. Hands down, for history buffs this unique museum is a top reason to visit Key West.

Strolling or cycling the Old Town is the perfect way to see Key West’s distinctive pastel-coloured homes. Nestled behind white picket fences, their porches are typically furnished with rocking chairs - the perfect setting for sipping iced tea in the balmy heat.

A saunter along Caroline Street or Greene Street will give you great glimpses of these late-1800s “conch houses”. Built in a mix-and-match style that fuses Victorian, Colonial and Tropical architecture, they’re raised on coral slabs and edged with gingerbread wood trimming. Fun fact - the reason they’ve lasted so long is that many were constructed by shipwrights using boat-building techniques.

If time is tight, you could take an Old Town tour aboard the Conch Train . It's a fun, fast and informative way of seeing a whole lot of sights, including Hemingway’s home and Harry Truman’s Little White House.

Head to the imposing  San Carlos Institute  on Duval Street to discover Key West’s fascinating Cuban history. The Institute has played a leading role in Cuban exile life since it opened on nearby Anne Street in 1871. It was here in 1892 that Cuban Revolution hero José Martí gathered exiles into a force that would achieve the island’s independence from Spain ten years later. The current building dates from 1924 and was financed by a grant from the Cuban government after a hurricane wrecked the original building.

Today it contains a permanent exhibition focusing on Martí and his followers alongside exhibits on Cuban presidents from 1902 to 1958 and a section on Cuban immigrants. San Carlos Institute is a Key West cultural highlight, for sure.

With Florida and the Keys frequently featuring in lists of top US National Parks , it's little wonder that Key West has its share of natural beauty.

For example, the Key West Butterfly and Nature Conservatory  is a paradisal oasis on Duval’s Street’s lower drag. With over fifty butterfly species and over twenty exotic bird species housed in a climate-controlled habitat, visitors can enjoy the dazzling experience of being surrounded - and settled upon - by dozens of its fluttering inhabitants.

More botanical beauty abounds at the  Audubon House and Tropical Gardens . The house takes its name from famed ornithologist John James Audubon, who was so taken with the property’s one-acre tropical garden that he made it his alfresco studio to paint regional birds when he visited in 1832. Twenty-eight of Audubon’s original lithographs are displayed in the house, which visitors are free to explore after a ten-minute guided tour.

For bird-watchers, butterfly buffs and appreciators of botanical beauty, these sites are top-of-the-list reasons to visit Key West.

Stunning roseate spoonbill in a Florida mangrove © Shutterstock

Next to the Key West Garden Club, this monument to a little-known, grievous chapter in American history commemorates the 294 African men, women and children who died and were buried here in 1860 as a result of the slave trade. During that summer, the US Navy rescued 1432 slaves from three American-owned ships headed to Cuba for illegal trading.

The freed slaves were given temporary residence in Key West, but after having suffered intolerable conditions during the crossing, nearly three hundred of them perished here from disease. Those who survived were given a return passage to Liberia in West Africa. But don’t expect to see any tombstones - West Martello Tower was built on the unmarked graves. The memorial itself is a cartographic mural depicting the ships' path and the community’s return to Africa.

While Key West isn’t as famed for its fabulous beaches as other parts of Florida , it has its share of pretty places to soak up the sun in style. Smathers Beach is the most bustling beach on the island, particularly at weekends when it draws local windsurfers and parasailers. This one-mile stretch of powdery sand is also a popular spot during Spring Break, and well-served by food trucks, umbrella rentals, and places to hire kayaks and jet-skis.

Given its popularity and proximity to the airport, Smathers Beach might not be the best spot to chill-out in peace, but it is perfect for trying your hand at water-sports and sampling Key West’s livelier side.

Beautiful Key West beach

1. Is Key West worth visiting?

If you’re looking for a multi-purpose destination - lively nightlife, exceptional water-sports, Old Town atmosphere, plus plenty of literary and political history - then quirky Key West should suit you down to the ground.

2. Why is Key West famous?

Thanks to its buccaneering history, Caribbean connections, picturesque pastel-hued houses, Ernest Hemmingway, iconic Key Lime Pie and legendary sunsets, Key West sure isn’t short of famous draws. What's more, its eclectic, off-beat vibe ( eccentricity is something Florida is famed for more widely) make it extra fun, and extra welcoming.

3. Why should I visit Key West?

One of the great things about Key West is how it suits a whole range of traveller types - groups of mates, couples, families, retirees. With plenty of museums, marine parks, water-sports and cultural attractions, it’s a top destination for those seeking a holiday experience that ticks a tonne of boxes.

4. Is Key West expensive to visit?

While it certainly isn’t the cheapest of destinations, with forward-planning it’s perfectly possible to enjoy visiting Key West within a budget - look to travel off-season (September and November are cheapest), take advantage of happy hour offers at the Seaport bars and restaurants, and research smaller guest houses and B&Bs. For great value, Caribbean charm, and scrumptious cinnnamon breakfast rolls, we recommend the Angelina Guest House tucked in the backstreets of Bahama Village.

At Rough Guides we’ve always taken pride in telling it like it is - whether we’re updating details in our guide books, or researching emerging destinations. With that in mind, we want you to know that when you click on links that lead to our affiliate partners’ sites, we can earn a small commission (at no cost to you). This is one of the ways we’re able to keep doing what we do best - provide you with travel advice and inspiration you can trust. Speaking of which, you can trust what we link to - our travel writer experts are exactly that (experts) and have highlighted them to share ideas that might make your trips all the more satisfying.

Header image: stunning Key West sunset © ventdusud/Shutterstock

Joanne is a Pembrokeshire-born writer with a passion for the nature, cultures and histories of the Caribbean region, especially Dominica. Also passionate about inspiring a love of adventure in young people, she’s the author of several books for children and young adults, hosts international writing workshops, and has written articles on the Caribbean and inspirational community initiatives for Rough Guides. Follow her @JoanneOwen on Twitter and @joanneowenwrites on Instagram.

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The Conch Connection

Secrets you don't know about historic key west.

Updated on: Feb 24, 2021 7:40:20 PM

Key West is positively a real-life Shangri La! The tiny island is approximately 4 miles long and 2 miles wide however, it can keep a “history nut” occupied for hours, days…..even weeks! Whether your interest is in the original settlers and inhabitants, politics, nature, architecture, famous residents or visitors including poets, writers, singers or pirates and treasures, marine life or quirky culture, Key West will have something to pique your interest.

Early native island residents named Key West “Cayo Hueso”, which translated means “Island of Bones”, or more commonly referred to as “Bone Island”. The island was actually used as a giant graveyard and was scattered with human bones!

The original inhabitants were believed to be Indians who had developed villages and structures on the island. The Calusa’s who were known to be peaceful, defended their territory when Juan Ponce De Leon “discovered” the new land in 1513. De Leon’s discovery did lead to the 16th century Spanish invasion, though he was not successful in conquering the Indians.  Here's a fantastic article detailing some of DeLeon's history in the New World .  

Photo Credit: Floridiana Facsimilie Reprint by University of Florida Press, Gainesville 1968

MORE READING

“Key West; The Old and The New” by Jefferson Beale Browne

Published in 1912, this version, eloquently and respectfully written was begun as a more detailed version of Walter Maloney’s documentation of Key West in their era.  An archived copy of his work can be found HERE . 

FAMOUS VISITORS and RESIDENTS

Key West has been a favorite destination for famous people throughout history including; Ulysses S. Grant, Grover Cleveland, William Taft, Calvin Coolidge, Harry Truman, John F. Kennedy, Dwight D. Eisenhower and post White House visitors were: Jimmy Carter, Bill Clinton and George Bush.

Other famous residents and visitors have included Ernest Hemingway, Tennessee Williams, Calvin Klein, Kelly McGillis,  Jimmy Buffet, David Allen Coe, Truman Capote,  John James Audubon, Mel Fisher,  Robert Frost  and Kenny Chesney….. among others.

Key West is littered with museums for every imaginable historic interest.  Below are just a few of the many that you will find.  Some  are a bit more elusive than others, but are none the less worthy of investigation.

• Key West Art & Historical Society “Custom House Museum”
• Flagler Station Oversea Highway Historeum
• Lofton B. Sands African Bahamian Museum
• Cayo Hueso Y Habana Historeum
• Key West Fire House Museum
• Key West Cemetery
• Hemingway House
• Heritage House Museum
• Florida Keys Museum of Natural History
• Oldest House and Garden Museum
• Fort Jefferson State Park - Dry Tortugas
• Fort Zachary State Park
• Key West Lighthouse Tower and Keepers Quarters Museum
• Naval Air Station Key West Visitors Center
• Fort East Martello Museum
• Truman Little White House
• Florida Keys Eco Discovery Center
• Key West Shipwreck Museum
• Mel Fisher Maritime Museum    

1884 Cartograph of Key West

Video Credit: Bravura Media Company

HISTORIC CUBAN INFLUENCE

During and following the war in Cuba, many fled to America’s southernmost city. The Cuban influence can be easily seen in the local culture, cuisine, art, landmarks, music and cigars. Cayo Hueso Y Habana Historeum is a great place to begin your Cuban History Hunt…. but be certain to leave plenty of time, and appetite to enjoy a few of the bevy of tantalizing dining options available. Many restaurants have some historic importance, as well.

ADDITIONAL INFORMATION

Some additional Key West fun facts and history hunter’s challenges include locating or visiting;

• The birthplace of Pan American Airlines
• The oldest restaurant, established in 1909
• The oldest island bar
• The first known island church/place of worship
• Pirate wrecks
• The resting place of the cemetery’s first guest
• Visit in February during the annual Civil War Heritage Days

Read, research and prepare for an exciting adventure….. then book your transportation with Key West Express!

Hero Image Photo Credit: Flip Schulke, Public domain, via Wikimedia Commons

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 100 Grinnell Street  Key West, FL 33040

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Marco Island

 951 Bald Eagle Drive  Marco Island, FL 34145

02 Oct A Photo Essay: Key West, FL

Somehow, Key West continues to draw me in with a tighter grasp every time I set foot on its sizzling shores. I have visited this tiny island paradise more times than I can count (and yes, I can count into double digits, thank you very much), and each time I discover numerous new activities that I never knew existed, and my ever-growing “to do list” keeps getting longer by the mile. The laid back island is so much more than Duval Street, “90 miles to Cuba” and Cheeseburgers in Paradise. There is a different and slightly adventurous side to the island believe it or not, and the vast amount of history is sure to turn heads on any pirate loving individuals. This past July was surprisingly my first time visiting Key West since starting this site, so it was fun to hop around and view the island with fresh eyes again, and with that, here is our photo essay of Key West, FL, and I’m sure it won’t be the last!

Ernest Hemingway used to frequent Sloppy Joe’s bar when it was located down the street. Now, the bar holds an annual Hemingway look-alike contest.

The multitude of statues surrounding the Custom House Museum are always fun to strike a pose with.

Old Town Trolley Tours and Conch Trains line the streets to give visitors a look into the past and current day Key West.

This antique shop near the Historic Seaport area felt more like a treasure trove with all it’s unique historic findings.

Air conditioning is a welcome treat when basking in the glowing sun all day long.

Knickknacks line the streets on the plentiful stands found throughout town.

Conch fritters are a popular treat that can be found throughout the island on most any menu.

Pirates are an integral part of Key West’s history and you are sure to find numerous sightings of the town’s shady and exciting past when wandering.

Getting out on the water is a great idea when visiting Key West. To date, our favorite vessel has been on a sailboat.

Sailing is hard work, but it still looks like fun–we watched the crew climb up into the sails.

Nautical rope adorns the side of the boat and looks quite nice against the setting sun.

Watching this plane fly overhead while riding along a schooner sailboat made us feel like we stepped back into time.

Parasails soar through the air as riders take in the beautiful, spanning views of the island.

The views really are great from up in the clouds, and it’s so much more peaceful than I would have ever thought.

Watching the jetpack adventures entertained us–maybe we can try it one of these days!

Fort Zachary Taylor State Historic Site is located off the beaten path in Key West. If you didn’t know it was there, you wouldn’t happen upon it.

At the park, you can find beautiful trees and great views of the ocean.

There are also plenty of picnic tables and a generous amount of shade in case you need a break from the sun.

The water at Fort Zachary was so clear–it makes a great spot for snorkeling if you don’t mind a rocky beach.

How far are you from Key West?

Directly off the shore from Mallory Square, rests Sunset Key. If you want to visit, make sure to get out your checkbook–it’s a pretty penny. For a more affordable way to visit, book a reservation at the island’s restaurant.

Even though Smathers Beach is man-made, it sure is paradise!

Wander around the Historic Seaport of Key West to find shops, restaurants and boats galore.

Despite the rundown look, the streets of Key West have an abundance of character.

The infamous “Southernmost Point” of the United States–when standing here you are closer to Cuba than Miami.

Mile Marker 0 marks the end of US Route 1. This road runs all the way from Canada to Key West.

This beautiful tree never escapes being photographed by us when we visit–it’s just so enchanting!

When visiting the beach at Fort Zachary Taylor, be sure to make a pit stop for a history lesson at the Fort. You will learn a bit about how the military protected the island many years ago.

No trip to Key West is complete without watching the famous sunset dip below the horizon.

Most visitors head to Mallory Square for the nightly Sunset Celebration, but a sunset cruise can be a peaceful and very enjoyable way to spend your last couple hours of daylight.

Street food perfect for those late nights out on Duval Street.

After the sunset celebration, the crowds move to Duval Street for some late night trouble.

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The Idea of Order at Key West

By wallace stevens, the idea of order at key west essay questions.

How are the woman and the sea alike, and how are they different? Why is this difference important?

Both possess a "voice" that the poem's speaker sees as having some inherent meaning, and they are both primarily perceived through sound. However, the sea cannot communicate in human terms; it lacks the mind and language to be understood in the same way. Even though the woman's song is inspired by the sea, it takes the sea's meaning and transforms it into something people who are listening can understand on an emotional level. This is the central point of the poem because it demonstrates the essential power of human creativity.

What effect does the woman's song have on the listeners?

The speaker is profoundly moved by the song, as he describes in the final two stanzas. His perspective on the world is temporarily shifted: instead of seeing the harbor and dark sea as he normally would, possibly feeling unsettled by fear of the unknown, he sees them suddenly as perfectly organized, mastered and tamed by the fishing boat lights. For the speaker, this is a reflection of the power of human intellect he has witnessed in the woman's song: the mind is able to create meaning out of the chaos of nature and impose "order" on it.

What is the significance of the title of the poem?

"The Idea of Order at Key West" correctly raises expectations for a highly philosophical, metaphysical poem. Key West is an apt setting for the poem because it allows Stevens the vibrant imagery of the beach and the sea as a symbolic encounter between human and nature. However, the Floridian island is less important than the mental acrobatics the speaker goes through while there. He is in pursuit of "order," the way in which human artists can make sense out of nature's confusion. Importantly, this order is first and foremost an "idea," more so than it is a concrete reality, because what changes after hearing the song is not the physical world but the way the speaker sees and thinks about the world. Therefore, the entire process of creation / meaning-making / changed perceptions happens inside the human mind.

Why do you think Stevens chose to break the poems into these stanzas, and what is the effect of the iambic pentameter?

The stanza order allows a steady progression of ideas: the first three stanzas build the speaker's thought experiment with increasing complexity, and then climaxes in the long fourth stanza, in which the divine creative powers of the woman are raised to their highest level. The strict metrical form is perhaps Stevens' own form of "order" imposed on the poem, giving it structure to counterbalance its abstract and hard-to-grasp ideas. The form also links his poem to a long tradition of lyric and epic poetry in which the divine spirit of inspiration, or the Muse, is of key importance. Since Stevens is directly tackling the question of poetic inspiration, the form helps bring his poem into indirect conversation with this prior legacy.

How is the sea characterized through imagery? Does the poem ever really decide what role the sea plays in the woman's song-making?

The sea is first and foremost a set of sounds, of crashing waves and water and a "cry" that the speaker hears. The physical images of the sea build up in stanza four, where it takes on monumental size and depth as an intimidating contrast to the lone woman. However, the tension between woman and water never really resolves into one fixed relationship. At different moments, the sea appears to be her inspiration (stanza two), or completely irrelevant (stanza three), or a subject to the new laws of reality created by her song (stanza four). Overall, the sea is a paradox, because its vast unknowability might inspire human artwork, but eventually human creations in turn dominate and redefine the sea on our own terms.

The Idea of Order at Key West Questions and Answers

The Question and Answer section for The Idea of Order at Key West is a great resource to ask questions, find answers, and discuss the novel.

Study Guide for The Idea of Order at Key West

Ideas of Order at Key West study guide contains a biography of Wallace Stevens, literature essays, quiz questions, major themes, characters, and a full summary and analysis.

• About The Idea of Order at Key West
• The Idea of Order at Key West Summary
• Character List

White Street Pier Key West: A Photo Essay

By far, our favorite pier in Key West was the White Street Pier, and it wasn’t because it was a few blocks’ walk away. (Scroll to the end to see our favorite night shot, btw.)

Almost 1/4 mile long and built in 1960, the White Street Pier has an incredible peaceful, sea-breezy charm about it. Morning, noon or night you can usually stroll along in relative calm amongst bike riders, dog-walkers, and kindred spirits taking a leisurely walk.

Take a look at the photos below to see why this is such an irresistible spot.

White Street Pier, Key West

UPDATE: The walls have been renovated since this snap!

At the End of the Pier Here you’ll notice stronger ocean breezes, and you’ll be amazed that these concrete walls have been holding strong since 1960 considering how they get pummeled with waves on a daily basis.

We really hope you make time to spend reflecting on White Street Pier and enjoying the unique views you can find here.

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11 Fun & Interesting Key West Facts Every Visitor Should Know

Are you looking for a place to spend your vacation that offers countless opportunities for beachgoing, marine activities, encounters with wildlife, and nightlife? Do you have an interest in touring museums stuffed full of pirate treasure or homes that were once owned by famous authors? How about experiencing some of the strange traditions still practiced in a place that views itself as its own republic?

Continue reading if you haven’t already started getting ready for your trip to Key West in order to pick up some more interesting information about this peculiar island. You’re going to want to start planning your next vacation to the Florida Keys as soon as you finish reading these fun facts about Key West.

A tour we think you'll love

1) Key West Is Called The Conch Republic

On April 23, 1982, the city declared its independence from the United States of America in response to a checkpoint set up by the United States Border Patrol at the entrance of U.S. Route 1 to look for drugs and illegal immigrants.

In spite of the fact that the holdups were mostly symbolic, the bureaucratic issues that resulted in them caused traffic jams of tourists trying to enter the island that stretched for 17 miles.

The inhabitants of the area began referring to themselves as “conchs” after Key West declared itself to be the “ Conch Republic .” This name continues to this day.

The Conch Republic Independence Celebration is an annual event held in April where Key West residents and visitors celebrate independence.

2) Key West Is Closer To Cuba Than Miami

This southernmost city in the United States is geographically located only 90 miles from Cuba , whereas Miami, which is one of the most populous cities in Florida, is located 150 miles away.

As a consequence of this, the island is saturated with Cuban culture , both in terms of its cuisine and its art. It is the site of the Cuban-American Heritage Festival , and it features an abundance of Cuban restaurants throughout the city.

3) Key West Is Connected To The Mainland By A Total Of 42 Bridges

Key West Florida is one of many islands that make up the Florida Keys, all connected by the Overseas Highway . In fact, many consider the Overseas Highway to be one of the most scenic drives in America. Finished in 1938, the Overseas Highway is 113 miles long, with a seven-mile bridge reaching Key West.

4) There’s No Longer A Key Lime Harvest

Everyone enjoys a delicious slice of key lime pie , but many people may be disappointed to learn that key limes are no longer cultivated or harvested on the island where the pie gets its name.

A few key lime trees that are privately owned still produce fruit in the Key West area, but the vast majority of the limes used to make the island’s signature sweet and sour treat come from the West Indies and Mexico.

5) Several Well-Known Authors Once Called Key West Their Home

Many people who go to Key West are interested in learning about its colorful history, particularly the large number of well-known authors who once lived there.

At his home in Key West, Ernest Hemingway penned some of his most notable works of literature. At the Ernest Hemingway Home and Museum , you can learn more about the author’s legacy, and during the month of July, the Hemingway Days Festival will pay tribute to the author’s works.

Not only Ernest Hemingway but also these authors also called the island home:

Tennessee Williams

Shel Silverstein

Robert Frost

Philip Burton

Elizabeth Bishop

6) The Little White House

One of the little-known facts about Key West includes how many presidents loved it. The structure known as the Harry S. Truman Little White House was initially constructed in 1890 as an officer’s quarters for a naval station in Key West, Florida.

Later on, President Howard Taft stayed there while he was on the island for a visit. In 1946, President Harry Truman got orders from his physician to get some rest, so he traveled to Key West and stayed at the home. He returned to Key West annually as part of his relaxation routine, bringing White House staff with him to continue presidential operations.

As a result, the property became known as the “ Little White House “. The following presidents have all been known to stay at the home:

Ulysses S. Grant

Grover Cleveland

Franklin D. Roosevelt

Dwight D. Eisenhower

John F. Kennedy

Jimmy Carter

7) The Southernmost Point

At the end of Simonton Street near Duval Street in Old Town , visitors will find a permanently anchored buoy known as the Southernmost Point . This buoy marks the southernmost point in the United States and provides an excellent photo opportunity at sunset.

Some people claim that this concrete buoy does indeed mark the southern point in the continental United States that can be reached by car, while others maintain that this is not the case, that another point on Key West island is further south.

Nonetheless, it is still a popular tourist stop. The previous marker, which was a wooden sign, has been replaced by this whimsical landmark, from which visitors assemble to view a breathtaking sunset.

8) The Atlantic Ocean Meets The Gulf Of Mexico At Key West

Because the Gulf of Mexico and the Atlantic Ocean meet in the middle of the Keys, the area around Key West is home to some of the most beautiful and unique ecosystems in the world.

Additionally, it is the location of the third largest barrier coral reef in the world , which is 170 miles long and stretches from Miami in the north to Dry Tortugas National Park in the west.

The combination of the deep ocean to the east and the shallow, flat gulf to the west creates the diverse ecosystem that is home to Key West’s flora and fauna.

9) A Mile-Long Pub Crawl

Some other little known facts about Key West include its adults-only entertainment. On Duval Street, you can do a mile-long pub crawl , which is perfect for those who enjoy an active lifestyle and alcoholic beverages.

Hang out at Hemmingway’s favorite watering hole , Sloppy Joe’s, or the original Margaritaville, owned and operated by Jimmy Buffett. In its entirety, the line of bars and establishments stretches 1.25 miles down Duval and is easily walkable.

10) There Are Ghosts On The Island

It is to be expected that a ghost story or two would linger in a place that has so much history surrounding it, and the abandoned forts at Dry Tortugas are not so far away. However, Key West itself is reportedly haunted, according to the locals.

After the sun has set, you can learn everything there is to know about Robert the Doll and the Key West Cemetery by going on the Ghosts and Gravestones Tour. Some people believe that the ghosts of Ernest Hemingway and Harry S. Truman roam the grounds of the famous museums known as the Hemingway House and the Little White House, respectively.

Additionally, some people believe that the ghost of the first female lighthouse keeper roams the grounds of the Key West Lighthouse and Keeper’s Quarters Museum.

11) Misconceptions Regarding Key West

People may have some preconceived notions about the island of Key West when they think about it, but here are a few of those notions that can be put to rest:

The place wasn’t always known as “Key West.” Cayo Hueso is the name that Spanish colonists gave to the island when they first arrived there. After some time, this was shortened to just Key West.

The key that is furthest to the west is not Key West. Dry Tortugas National Park is located an additional 70 miles to the west of where the Florida Keys begin.

Although Jimmy Buffett does not currently call Key West home, he is said to maintain ownership of a property on Windsor Lane.

It was by chance that Key West was discovered. Juan Ponce de León, a Spanish explorer, is credited with being the first European to arrive in Key West in the year 1513.

Bet You Didn’t Know These Key West Facts

Now that we’ve cleared up some of the confusion surrounding Key West, what are some facts about the island that you were previously unaware of?

In the 1830s, the locals’ primary source of income was the salvage of sunken ships. By the year 1889, Key West had become the most populous and wealthiest city in the state of Florida.

Pan American airlines got its start in Key West. Pan American Airways began regularly transporting passengers and mail between Key West International Airport and Havana, Cuba, in 1927.

John Simonton privately paid $2,000 to acquire Key West in the year 1882.

Both the Calusa people who lived there before and the Spanish colonists were forced to move to Cuba. There are three forts from the Civil War located in Key West.

Both Sunset Key and Wisteria Island, which is also referred to as Christmas Tree Island , are artificially created islets. Sunset Key is home to opulent homes and resorts.

All of the cats that live in the colony at the Hemingway House are descended from the same six-toed cat that belonged to the author , and they all carry the same genetic mutation.

The Seven Mile Bridge is listed on the National Register of Historic Places

These interesting tidbits about Key West are just some of the many wonderful things about the area that attract visitors and make it such an interesting place to visit. Key West’s diverse culture has something for everyone.

In addition to enjoying shopping excursions to Mallory Square and Duval Street , tourists in Key West also take pleasure in riding the Old Town Trolley tours near Mallory Square, going to the Key West Aquarium , and taking the ferry out to Sunset Key to drive among the luxurious homes on that island.

We hope that after reading some of these facts about Key West , you will decide to make a trip there during your next vacation. Call Key West Sandbar Tours at this very moment to book your next exciting Key West excursion and find out more information about the available activities sure to keep you entertained when you next visit Key West.

Sandbar Tour For Large Groups

If your group is larger than 6 and you have a hard time finding a boat ride to the sandbars because of the 6 passengers limit, we are here to help. You can book our 2 identical Hurricane 27 foot deck boats and our captains will drive them side by side so you can take cool photos and they will raft up the boats on the sandbars so you can enjoy and share this amazing time together.

Hopping Sandbars In Key West

What a perfect day to take a boat ride! You will see not one but several different sandbars on this tour! It will only take 25 minutes to get there on our epic adventure, and we can stop as long as you want at those sandbars that interest you the most. This is something you cannot miss!

Experience the mangrove trails of Mud Keys and hang out with locals at Snipe Point after. You won't want the day to end.

Key West Sunset Cruise

Ocean, meet our captain! One of the best things about the backcountry waters is how it’s never too crowded. So jump in and enjoy the peacefulness and remoteness as you stand in the "middle of the ocean" with nothing but water around you. Optionally, bring some champagne to enjoy with the sunset as a backdrop. Then, just sit back and relax as you cruise on out into the middle of nowhere, leaving behind any stress or worries.

Mud Key Mangrove Safari

It's time for some adventure and excitement with a boat trip through the backcountry. After only a short ride, we'll take you on a leisurely cruise down to Mud Key Sanctuary, where you can enjoy the countryside and take in all the wonders of nature that surround you. Stop by the sandbar for a refreshing dip or just stroll around and soak up the sun. Capture your memories and cherish them forever.

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Truman foundation announces student essay contest.

The Key West Harry S. Truman Foundation, in partnership with the Society of Presidential Descendants, is conducting its second annual essay competition for Monroe County high school students.

The top three winners will be invited to attend the upcoming annual Harry S. Truman Foundation Presidential Families Weekend forum held at the Harry S. Truman Little White House in Key West, where as part of their prize package the students will be seated at a reserved table to experience a moderated discussion among descendants of U.S. presidents. Following the forum, presidential descendants will introduce the winners to the audience and present them with cash prizes and certificates of achievement.

Submitted essays should reflect this year’s forum theme, “Political Maneuvering: The Powerful Influence of the Presidency.” Essays will be juried by members of the Key West Harry S. Truman Foundation and the Society of Presidential Descendants, and judged on factors that include the author’s skill at presenting the subject compellingly according to competition guidelines. The competition is open to all Monroe County students, including home-schooled and charter-school students, currently enrolled in grades 9-12, and who have performed volunteer service work within the past two years.

Monroe County School District social studies coordinator Jennifer C. Barrios serves as liaison between the school district and the competition organizers, and accompanied last year’s winning students to the forum.

“The opportunity for our students to hear personal stories from presidential descendants that are not written in textbooks or taught in any classroom was priceless,” Barrios said. “And it was really wonderful to see how the forum audience flocked to the winners to talk with and congratulate them at the event. Even the descendants were telling them how impressed with them they were.”Deadline for essay submissions is Jan. 15, 2024. To request essay guidelines and submission information, email Michael Ables at [email protected] .

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Your Guide to a Florida Keys Road Trip: Key Largo to Key West

Posted: March 12, 2024 | Last updated: March 13, 2024

Your road trip guide to the Florida Keys

One of the best state road trips in America has to be the sun-kissed drive from Key Largo to Key West in the Florida Keys. This road, known as the Florida Keys Overseas Highway, takes you through a 125-mile island chain that begins just south of Miami. It hopscotches over 42 bridges and five islands, and has turquoise waters stretching in every direction into the Atlantic Ocean, Florida Bay and Gulf of Mexico.

So if you're looking for the perfect Atlantic Coast road trip or cheap beach vacation , look no further than this road trip guide from Key Largo to Key West. And if you'd rather travel from Key West to Key Largo, rest easy—the route works either way. There are shuttles that run from Key Largo to Key West, but keep in mind, you'd be missing out on all the fun in between.

By the way, once you embark on the Florida Keys Overseas Highway, you'll notice that many sites along the way use mile markers (MM) in their address. We use those mile marker points in this story to help you navigate the drive.

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Mile marker: 108–90

The first of the Florida Keys you'll hit after driving about an hour south from Miami en route from Key Largo to Key West is, well, Key Largo. Often referred to as the Dive Capital of the World, Key Largo includes one must-see stop: John Pennekamp Coral Reef State Park (MM 102.5), the first underwater preserve in the United States.

Experienced and novice snorkelers and SCUBA divers will be enthralled by the teeming marine life that lives just below the water's surface, like parrot fish, barracudas and sea turtles. More experienced divers enjoy exploring the USS Spiegel Grove, one of the largest ships ever intentionally sunk to create an artificial reef where pretty fish can thrive.

Back on dry land, travelers can wander nearly six miles of trails at Dagny Johnson Key Largo Hammock Botanical State Park, home to more than 80 species of plants and animals. You can also peruse the work of local artists at myriad galleries.

Best beach: Cannon Beach, found within John Pennekamp Coral Reef State Park, has shallow waters that are perfect for wading. You may even spot cannons and anchors on the beach that remain from a 1715 Spanish shipwreck.

Where to eat: Dig into the catch of the day at The Fish House, Key Largo Conch House or Snook's Bayside Restaurant & Grand Tiki Bar, some of the best traditional restaurants in the area. If you'd rather turf than surf, check out Jimmy Johnson's Big Chill.

Where to stay: If you can't get enough of the underwater world, stay at Jules' Undersea Lodge , the world's first underwater hotel. If you'd rather keep dry, try the adults-only Bungalows Key Largo .

Mile marker: 90–63

Next up en route from Key Largo to Key West is the fisherman's paradise known as Islamorada. Considered the Sport Fishing Capital of the World, it's where backcountry sport fishing and saltwater fly-fishing got their start. Countless seasoned boat captains are ready for hire to take you out to catch the wahoo, marlin, mahi-mahi and tuna that swim in these waters.

There's an even quirkier way to interact with fish here: hand-feeding the tarpon off the docks of Robbie's Marina (MM 77.5). Since 1976, countless Keys visitors have stopped to feed them, and more than 100 kinds of fish gather at the docks for their daily snacks. Feeding the fishies there is so popular, it's been named the No. 1 activity in all the Florida Keys.

Islamorada is also a terrific spot to kitesurf, stand-up paddleboard, go for a hike or take a bicycle ride. Stop by the Laura Quinn Wild Bird Sanctuary, where injured or displaced birdies now make their homes. Or visit the History of Diving Museum, which boasts one of the world's largest collections of diving helmets.

Best beach: Anne's Beach is popular with families (and dogs) because of its shallow waters and lack of waves. Take a walk along the boardwalk or enjoy a picnic at one of the covered tables.

Where to eat: For a quintessential casual Florida Keys meal, go to the Hungry Tarpon. If you want more elegant fare, make reservations at Chef Michael's for creatively inspired local dishes.

Where to stay: When it's time to lay your head for the night, check in to one of the new oceanfront suites at Cheeca Lodge & Spa , or your own cottage at The Moorings Village & Spa .

Mile marker: 63–40

Marathon is the island chain's top boating destination—and for good reason. The area boasts nearly 2,400 boat slips and plenty of facilities to accommodate sailors passing through. But you don't need your own boat to enjoy Marathon and its waters.

For a truly different experience, hop on over to Cruisin' Tikis and have a floating tiki bar adventure. Sunset, mangrove and harbor cruises are all available, as is a swim-stop cruise for a chance to jump into the water.

While you're here, you should also visit Pigeon Key, an island that is accessible by boat, trolley or walking the 2.2-mile Old Seven Mile Bridge. It has a museum to explore, either on a guided tour or on your own. The Bridge is open for walking, running, bicycling, rollerblading and, of course, watching the killer sunrises and sunsets.

Best beach: Sombrero Beach is one of the prettiest beaches in the Florida Keys—not to mention one of the best beaches in Florida . And it's not just popular with humans; sea turtles nest here between April and October.

Where to eat: For any meal, stop by Castaway, which has been serving guests for more than 70 years. Or make a night of it at Hide Away Café, which has an extensive wine list.

Where to stay: The Faro Blanco Resort & Yacht Club is set on the waterfront and gives you a taste of marina life. Lime Tree Bay Resort on Long Key has spacious townhomes for rent.

The Lower Keys

Mile marker: 40–4

After crossing the Old Seven Mile Bridge out of Marathon, you'll find yourself in the Lower Keys, where natural habitats and wildlife refuges thrive. It's no wonder this part of the Florida Keys is known as the Natural Keys. You might even want to consider taking an electric vehicle on this road trip so you don't disturb the animals.

Your best chance to spot a native Key deer, a subspecies of the Virginia white-tailed deer that somehow made its way south, may be in the National Key Deer Refuge, comprised of 9,200 acres stretching from Bahia Honda Key to Sugarloaf Key on the edge of the Gulf of Mexico. More than 20 endangered and threatened plant and animal species can be found within the refuge. Take a quiet walk at dusk or dawn for your best chance to glimpse a Key deer, or join a ranger-led tour to learn more about the area.

Aside from all the eco-friendly fun, Stock Island is well worth a stop. Their maritime history goes back generations, and the marina is filled with shrimping and fishing boats. Artists have been flocking to Stock Island, too, and share their works in galleries dotted across the small island.

Best beach: The shallow, clear water and white sand at Calusa Beach make it a locals' favorite. The beach is a perfect spot for snorkeling too.

Where to eat: In addition to the freshest of seafood, Big Pine Rooster serves up ribs and a special-recipe meatloaf. Or sip like the locals at No Name Pub, located on Big Pine Key.

Where to stay: Consider the waterfront Sugarloaf Lodge , stay in an Airstream at Big Pine Key Resort  or pop a tent on one of the reserved campsites at Bahia Honda State Park.

Mile marker: 4–0

You've made it to the end! Closer to Cuba than Miami, Key West is known for its nightly sunset celebrations, party atmosphere and laissez-faire vibe, but it's really so much more.

If you're a writer or bookworm, you'll certainly want to make plans to visit the Ernest Hemingway Home & Museum, where you should keep an eye out for the famous six-toed cats. Then wander through Key West's Bahama Village, a 12-block area of historic homes and restaurants.

Consider a day trip to Dry Tortugas National Park, about 70 miles west of Key West in the Gulf of Mexico, where you'll find some hidden gems . The island, accessible by boat or seaplane, is popular for snorkeling and feeling like you're on your own private island, not to mention touring the Civil War–era fort.

Best beach: Fort Zachary Taylor Beach—or Fort Zach, as locals call it—predates the Civil War and boasts the island's very best sandy stretch.

Where to eat: No visit to Key West is complete without a meal at Blue Heaven, where you can dine with wandering roosters for breakfast, lunch and dinner. Or snag a spot on the tiny balcony at Santiago's Bodega for tapas and flowing wine.

Where to stay: The boutique Gardens Hotel , the adults-only Kimpton Hotels Ridley House  or the new Capitana Key West , to name a few. Wherever you stay, you're sure to find your place in Key West, and it's likely you'll follow so many others' lead and start planning your return visit before you even leave.

Art and history in the Florida Keys

Road-tripping from Key Largo to Key West, it's easy to appreciate all the natural beauty. That said, the Keys aren't just a terrific destination for eco-travelers, but artists and history buffs too.

It's easy for artists to find inspiration throughout the Florida Keys. Fortunately for road-trippers, there are many spots to stop and admire their work. One of the largest artists' communities in the Florida Keys is Stock Island in the Lower Keys, just about three miles from the commercial area of Key West. What was once a shrimping boat marina is now a blend of fishermen and painters, sculptors and other artisans who have created an energetic and supportive community.

For history buffs, in addition to Pigeon Key in Marathon and the Civil War–era Fort Jefferson in Dry Tortugas National Park, other must-stops in Key West include the Audubon House & Tropical Gardens, Harry S. Truman Little White House and the Southernmost Point in the continental United States.

Planning your Florida Keys road trip

Now that you're inspired to hit the road, it's time to start planning. After budgeting for a road trip , your next step is to decide whether you will travel south from Key Largo to Key West, or north from Key West to Key Largo. Or maybe you'll opt for a roundtrip.

If you're starting off in Key Largo, it's important to note that the Florida Keys Overseas Highway begins at the Miami-Dade/Monroe County line. So if you're flying to Florida, Miami International Airport (MIA) is the way to go. If you begin in Key West, the airport (EYW) is on the island.

If you're already driving one of the best road trip cars to get to Florida, you're all set. But if you need a loaner, choose one of the best cars to rent for a road trip . Consider packing these road trip essentials and download some of the best podcasts for road trips to make the miles fly by.

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