Get ready for the ultimate selfie. The Southernmost Point (at Whitehead and South streets) marks the spot where there are a mere 90 miles between the United States and Cuba. The City of Key West constructed an 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. Admission is $13 for adults and $6 for kids.
There’s no doubt that Duval Street occupies the heart of all the action 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.
Kayak or stand-up paddleboard through mangroves and 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. Rentals start at $30 per person.
Paying homage to Key West’s maritime heritage, the Key West Lighthouse & Museum, run by the Key West Art & Historical Society dates back 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 who held the position during that period. Admission is $10 for adults and $5 for kids.
Key West is famous for its dazzling sunsets, so set sail for an evening that’s 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. Excursions start at $40 for adults and $20 for kids.
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, Tennessee Williams, Jimmy Buffett, and, of course, the legendary Captain Tony himself.
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.
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.
Cruise around the island via bicycle and revel in the warm tropical breeze and Key West sunshine. Many of the hotels around town offer bicycle rentals to guests and it’s the perfect way to see the sights, as well as ditch the headache of trying to find parking.
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. Nosh 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. 310 Duval St., Key West, FL 33040, 305-294-7511
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. Admission starts at $12 for adults and $8.50 for kids.
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. Ferry rides start at $175 for adults and $125 for kids (includes park entrance fee).