The best of Key West, tailored to your travel style

There’s not a place on earth that can squeeze more beauty, art, history, eccentricity and spontaneous fun into four square miles than Key West.

Set at the very end of The Florida Keys archipelago, the island is geographically closer to Cuba than Miami, but there’s no passport required to visit the "Conch Republic." Key West is famous for its connection to icons like Ernest Hemingway, President Harry S. Truman and Jimmy Buffett. It’s known, too, for its nightlife, legendary fishing and LGBTQ+ scene. But what some may not know is that the island is home to attractions perfectly suited to family trips, friends getaways, cultural explorations and foodie adventures, too. Read on for some must-try Key West experiences tailored to you and your traveling crew.

For the history & culture seeker

The story of how Key West came to be one of the country's most intriguing places is fittingly full of twists and turns. Traces of the various cultures who have inhabited the island—the Indigenous Calusa, Spanish explorers, English settlers, Bahamian and Cuban immigrants—can be seen and felt in the island's landscape, architecture, cuisine and attractions. 

And those looking for a firsthand view into the people and places that have been influential in shaping Key West will find a number of experiences available. Amid its two floors of art and artifacts, the Key West Museum of Art & History at the Custom House includes an exhibit on Henry Flagler's Overseas Railroad, the seemingly impossible—but ultimately successful, if short-lived—venture on which the Standard Oil tycoon spent $30 million of his own money.

Meanwhile, the Hemingway Home & Museum—undoubtedly one of Key West's most famous sites—is an experience not to be missed. With a tour of the lauded 20th-century author's home, you'll get to spend time in the meandering gardens. Admire the estate's numerous cats (about 60 of them), some of whom are six-toed descendents of the author's own pets. Plaques around the property reveal little-known tidbits about the author's life (spoiler alert: he was an avid boxer), while the tour of the home's interior brings you right into the spaces where the author wrote and lived for nearly a decade.

The Harry S. Truman Little White House—the only presidential museum in the state—was the "winter White House" of the 33rd president from 1946 through 1952. Originally built in the late 1800s as housing for officers of the Key West naval base, President Truman used the home as a working vacation residence, spending 175 days there in total. Seven other U.S. presidents—including John F. Kennedy and Bill Clinton—have also stayed in the home. Take a tour of the historic 9,000-square-foot building with narration by a knowledgeable guide who will share the inside scoop on how Truman ran pivotal aspects of the administration from his home. 

Unwind with a stroll through the charming Key West Historic Seaport to take in views of the water, where fishing boats, yachts and other vessels line the docks. Grab a bite at one of the many waterfront eateries—seafood at Conch Republic Seafood Company, Half Shell Raw Bar or the Schooner Wharf Bar, for example. There are also myriad souvenir shops, boutiques and galleries to peruse. 

End the evening—or get it started, if you're going to hit the famous Key West nightlife—with a sunset cruise. Hop on a catamaran, party boat, schooner or even a glass-bottom boat and kick back with a cocktail as the sun makes its stunning descent over the water. 

For families

Key West is a dynamic and fun getaway for families, with cool and quirky architecture, art, street performances, historic sites and nature attractions to experience at every turn. It's also incredibly easy to find family-friendly events and activities to "dive" into—for example, snorkeling tours. A wide variety of outfitters offer such outings with expert guides, and many include special extras like cocktails, snacks, dolphin viewing or kayak excursions. These tours will transport you to some of the top snorkel sites, many of which are located in protected marine parks.

Sand Key Lighthouse Reef, for example, is a partially submerged mid-19th-century red iron lighthouse that's often surrounded by large schools of parrotfish, trumpetfish, angelfish, nurse sharks and sea turtles. The Eastern Dry Rocks, too, is an excellent spot to snorkel, with coral canyons that harbor marine life from stone crabs to octopus, rays to barracuda—plus a colorful array of tropical fish.

If you've got more time, a day trip to Dry Tortugas National Park, set 70 miles west of Key West and reachable by sea plane, private boat or ferry, is an amazing experience for all ages. In addition to great snorkeling, the islands have pristine white-sand beaches surrounded by electric-turquoise waters, a historic fort built in the mid-1800s and intriguing bird populations to observe. It's even possible to camp under the stars on the remote island of Garden Key if you plan way ahead—reservations are typically snapped up months in advance.

The maritime exploration continues on land at the Key West Shipwreck Treasure Museum, an immersive experience that transports visitors to the Key West of 1865, when pioneers on the island sustained themselves through the practice of wrecking—that is, salvaging goods and treasures from vessels that wrecked on treacherous reefs in the surrounding waters. Kids will be fascinated to view real artifacts from the wreck of the Isaac Allerton, an American merchant ship that sank in 1856 and was rediscovered in 1985. 

Taking place each evening, the Mallory Square Sunset Celebration is a Key West fixture. As the sun draws lower, talented buskers—jugglers, acrobats, musicians and comedians—take turns in the limelight, performing their impressive acts, often with a good dose of humor and audience participation woven in. 

For a friends getaway

Key West is a fabulous spot to travel with friends; there are so many cafes, shops, galleries and bars to pop into, and so many curiosities to check out that any group would find plenty to do, itinerary or no. That said, laying out just a few plans will help you and your pals soak up more of Key West's unique appeal. 

A Key West bike tour, for example, will make you feel like a local, taking you through hidden lanes and quiet streets to historic homes and notable sites. As you pedal from block to block, you'll see examples of iconic conch-style architecture, Victorian mansions and quaint cottages painted in cheery pastel hues. In true island style, the unhurried tour—led by a Key West native who goes by "Lloyd"—includes stops for smelling tropical flowers and sampling foraged fruit. 

The Key West Butterfly & Nature Conservatory is another delightful experience to share with friends, though families, couples and solo travelers will have an unforgettable time, too. Set inside a soaring glass-domed space, the conservatory is home to hundreds of free-flying butterflies from around the world, plus exotic birds—purple honeycreepers, vibrant tanagers and flamingoes included—in a rainbow of colors.

As you walk the lush garden path, you'll be cocooned in a sensory bath of balmy air, birdsong and the flutter of paper-thin wings at every angle. There's even a nursery where you can see butterflies in all phases of metamorphosis as they prepare to join their friends inside the tropical dome.

Of course, an evening spent on legendary Duval Street will add color to any Key West getaway. Lined with eateries, shops and bars as various as they are numerous, Duval stretches about 1.5 miles from the Gulf to the Atlantic.

Your crew can hop from one character-rich pub to another, sip Rum Runners, local microbrews and funky craft cocktails, dance to lively sets from local bands and trade stories with locals and fellow visitors along the way.

For flavor chasers

Whether you're hankering after a slaw-slathered Grouper Reuben, a succulent plate of Key West pink shrimp or a lime-laced blackened snapper taco, you're guaranteed to find it amid Key West's hundreds of restaurants.

Try the upscale island-inspired menu at Flamingos: A Richard Blais Key West Kitchen, which boasts incredible water and sunset views on top of its Top Chef-curated menu. For a big night out, try the surf and turf dinner for two, combining cowboy steak, Caribbean lobster tail, a variety of veggies and coconut rice with drawn butter and chimichurri sauce. 

Louie's Backyard is another favorite, offering a choice of waterfront patio seating and dining in a second-floor cafe with water views. (The menu is a bit more limited upstairs; reservations are recommended for the outdoor patio/main restaurant.) The menu features everything from small plates (the conch fritters with hot pepper jelly and wasabi are a popular choice) to dinner-ready salads to seafood-forward mains (the shrimp and grits are top-notch). There's an excellent brunch Saturdays and Sundays, too. 

For a more casual bite, the Boat House Bar & Grill hits the spot without skimping on the waterfront views. Its nightly happy hour (4-6:30 p.m.) features over a dozen small plates like wings, conch chowder and mini filet mignon kebabs, plus well cocktails and select wines and beers, all at half off. For dessert, pick the sticky toffee pudding, which Woman's World Magazine recently described as "the best dessert in all of the Keys."

Whether or not you agree, no visit to Key West would be complete without a fat slice of key lime pie. Kermit's Key West Key Lime Shoppe on Duval Street is a one-stop-shop for every iteration of the classic Keys dessert. Beyond the traditional cream-topped slice, you can try the pie frozen on a stick and dipped in chocolate, or pick up key lime pie-inspired cookies, candies, cakes and gifts (candles and lip balms, for starters).

Connoisseurs of craft beers and spirits will find plenty of opportunities to taste local wares in Key West as well. Stop in at First Flight Island Restaurant & Brewery, located in a restored historic building that served as the humble headquarters for Pan American Airways when it began service in 1927. Its location also makes it the southernmost microbrewery in the continental United States. Its three home-brewed beers include Captain Maverick IPA, touted for its clean crisp finish, and citrus wheat beer Sunset Clipper, with notes of grapefruit and coriander.

To sample locally distilled rum, head to Key West First Legal Rum Distillery. There, you can get in on a free behind-the-scenes tour of the facility, buy a bottle of authentic Key West rum to take home and even book a mojito-making class that includes expert instruction and a kit to take with you. 

For LGBTQ+ travel

If you're looking for a Florida destination that's an exceedingly good fit for LGBTQ+ travelers, Key West is an easy choice—it's an island that lives up to its motto, existing harmoniously as "One Human Family." Key West has been openly queer-friendly for decades, hearkening back to the mid-20th century when Tennessee Williams became a regular visitor and then resident. Following that, the island came to be governed by some of the country's first openly gay elected officials.

Today, LGBTQ+ culture is an integral part of everyday island life; the calendar is peppered by LGBTQ-forward festivals year-round (Womenfest, Key West Pride and Fantasy Fest are just a few examples), many businesses are gay-owned and happenings like drag brunches are seamlessly woven into everyday life. 

Celebrate Key West's gay culture with a Vespa tour that highlights key sites in the island's LGBTQ+ history. Visit the Tennessee Williams Museum, for example, set inside the home where the celebrated American playwright (A Streetcar Named Desire; Cat on a Hot Tin Roof) once lived with his partner Frank Merlo. The museum preserves one of the largest public collections of his personal mementos and works, also clarifying how Williams' presence and influence helped to shape Key West's literary and cultural identity.

You can even experience Key West's LGBTQ+ culture out on the water. Blu Q is a gay sailing adventure company that offers a variety of fun water sports and sailing activities, including clothing optional all-male sailing excursions and all-welcome sunset sails, plus charters, snorkel trips and kayak tours.

When it comes to dining plans, it's easy to weave in some delicious meals at gay-owned restaurants around the island. Consider booking brunch or dinner at Azur, where the menus fuse local Floridian flavors with those of the Caribbean and the Mediterranean. You'll also find influences from Tuscany and Germany, where chef-owners Michael Mosi and Drew Wenzel honed their culinary skills.

Or reserve a table at The Flaming Buoy Filet Co., a supper-club style eatery that's at once homey, sassy, artsy and quirky (the decor leans heavily on a Star Wars theme, just as one example). The lobster mac & cheese is a universal favorite, and their happy hour menu, available between 4 and 6 p.m., is not to be missed.

Ready to go? Start your own unique Key West adventure today.