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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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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