The 20 Best Things To Do in Key West

Launch a kayak or stand-up paddleboard through mangroves and float out to crystal clear water where you can jump in and go for a swim with sea turtles, tropical fish, and maybe even a dolphin or two. Lazy Dog Kayaking and Paddleboarding offers group tours and private charters, plus fun classes like PaddleYoga.

Pay homage to Key West's maritime heritage with a trip to the Key West Lighthouse & Museum. It's run by the Key West Art & Historical Society and dates to the 19th century. Climb the 88 steps to the top and learn about Barbara Mabrity, the first lighthouse keeper and one of the only women in history to hold the position during that period.

Get ready for the ultimate selfie. The brightly colored buoy of the Southernmost Point (at Whitehead and South streets) marks the spot at which there are a mere 90 miles between the United States and Cuba. The City of Key West constructed the oversized concrete buoy in 1983 and the landmark has been one of the most photographed places on the island ever since.

With so much history and folklore on such a small island, you'll find plenty of museums to explore. Start with the Ernest Hemingway Home & Museum in the heart of Old Town Key West. Wander through the Nobel Prize winner's lushly landscaped abode and make friends with one of the infamous six-toed cats.

There's no doubt that Duval Street is the heart of all the activity in Key West. Stretching from Mallory Square to the Southernmost Point, this main drag is lined with outdoor cafes, funky boutiques, art galleries, and some of the most famous bars and saloons in the country.

You've explored the city, now lounge on the shore. Play a game of beach volleyball; splash in the aquamarine water; take out a mini sailboat; or just find a perch, lay a beach towel, and take in the view. Seek out Smathers Beach, Higgs Memorial Beach Park, Dog Beach, and Rest Beach for sun and sand.

Key West is famous for its dazzling sunsets, so set sail for an evening steeped in equal parts tradition and natural beauty. Fury Key West offers a variety of sunset cruise options from romantic champagne-style trips to lively rum and reggae parties. Head to Mallory Square to see the sunset from dry land.

Inspired by the tropical landscape and eccentric local culture, artists have long called Key West home. Browse the many art galleries that line Duval Street, including Gallery Uno, home to works of art by long-term island resident Alberto DeAndrea. Stop into Gallery on Greene (located on Greene Street) too.

Satisfy your sweet tooth with a slice (or three) of delicious Key lime pie. Kermit's Key Lime Shoppe has been a Key West mainstay for decades and offers everything from Key lime pie and homemade taffy to Key lime mango chutney and citrus salsa. You can also find it at the Key West Key Lime Pie Company and the Southernmost Key Lime Shop.

Cruise around the island via bicycle and revel in the warm tropical breeze and Key West sunshine. There are lots of bike rental services, and many of the hotels around town also offer bicycle rentals to guests. It's the perfect way to see the sights, as well as ditch the headache of trying to find parking on the island.

Ready to eat your way around Key West? Start at Caroline's Café located at the historic Dr. Joseph Y. Porter House on Duval Street. Dine on classic Key West conch fritters or Caroline's Famous Fish Sandwich. Then cool off with a handcrafted cocktail at Caroline's Other Side, a speakeasy style bar connected to the cafe.

Home to hundreds of vibrant butterflies, the Key West Butterfly and Nature Conservatory is truly a sight to behold. You'll find lush gardens, cascading waterfalls, and more than 50 species of the winged beauties. Keep an eye out, because you may happen upon the resident flamingos too.

Comprised of seven islands located about 70 minutes by ferry boat off the coast of Key West, Dry Tortugas National Park is home to Fort Jefferson, one of the nation's largest 19th century fortresses. Charter your own boat or hop aboard the Yankee Freedom ferry for a ride out to paradise.

There's lots of great coffee to be found on Key West, and ordering up a cup is a great way to start a day of exploring. There are several locations of Cuban Coffee Queen around town, including on the waterfront and downtown, so you're never far from a freshly roasted cup. Try Key West Sunrise for a medium to dark roast or Smooth Sailing for decaf.

During your visit, make your home base The Southernmost House, an adults-only boutique hotel on the waterfront. Built as a mansion in 1897, legend has it that Thomas Edison installed all the electricity in the house himself, and he left his personal phonograph as a present when he departed.

One of the most memorable cool treats on Key West is Key Lime Pie on a Stick, a delicacy that comes about when a slice of tart key lime pie is dipped in a chocolate shell. You can order yours at Kermit's Key West Key Lime Shoppe.

Order up fresh seafood at Eaton Street Seafood Market on Eaton Street, where you'll find crab cakes, fresh seafood salads, and chowders. They also have the best lobster rolls in town. You can  find kits there that will help you make your own fresh Key West lobster rolls too. On the menu at the restaurant are seafood baskets, grilled lobster tails, and crab cake sandwiches, so you'll want to come hungry.

It's no secret that Key West is home to an impressive share of eclectic watering holes. There's no better place to start your bar hop than Captain Tony's Saloon. Originally opened in 1851 as an icehouse that doubled as a morgue, this old-school pub has attracted the likes of Ernest Hemingway, Jimmy Buffett, and, of course, the legendary Captain Tony himself.

Key West is all about great entertainment. Head to Mallory Square for the nightly sunset celebration featuring local artisans or the Key West Amphitheater for big shows. When you're in town, also try to catch one of the live concerts from COAST or  their annual music and arts festival.

To see the island on a swift spin through town, hop aboard a sightseeing tour. Book your spot on the Old Town Trolley Tours or the Conch Tour Trains for a fun train ride and a quick introduction to the island and its sights.