For island-obsessed travelers, Key West is Florida’s most tropical, most funky and most laid-back destination, where days are packed to the brim with things to do. Here’s our list of 10 fabulous ways to experience this very cool island, after you’ve lolled on the beach and drank margaritas poolside of course.
1 Cruise with the Sun
Sail off into the sunset on a catamaran while Jimmy Buffett tunes play and margaritas flow. This is one of the best ways to sightsee from the water and get in the party mood. A popular choice is the Commotion on the Ocean Fury cruise that departs from the Historic Seaport. The two- hour trip into the Gulf sails pass Sunset Key and alongside Mallory Square, where sunset gazers congregate at dusk. Bring a camera because the day’s-end views are spectacular.
2 Pay Homage to Papa
The name Ernest Hemingway is bigger than life on this tropical island. The spirit of the American novelist, who lived in Key West in the 1930s and wrote To Have and Have Not while on the island, is evident in the Ernest Hemingway Home and Museum. Visit the two-story house and its tropical garden, which are still occupied by descendants of Hemingway’s cats (said to have six toes). The writer’s old typewriter, period furniture from Spain and a vintage safe are among the intriguing items on display.
3 Go Treasure Hunting
Poke into the Mel Fisher Maritime Museum to learn about the fascinating story of underwater treasure hunting. Artifacts from the 1622 legendary Spanish galleon Nuestra Senora de Atocha, which sunk off Key West, were recovered by diver Mel Fisher and his team in 1985. Exhibitions feature gold and silver bars, coins and an impressive gold chalice among other treasures. Photographs documenting Fisher’s underwater excavations are also on display.
4 Discover the Key Lime
One must-stop is Kermit’s Key West Key Lime Shoppe on the corner of Greene and Elizabeth streets. Dressed in traditional baker attire, Kermit Carpenter welcomes customers to his cheery lime green-and-yellow cottage store. Sample his tart yet sweet, creamy pie with a graham cracker crust and swirls of whipped cream, but also take home a bag of Key lime taffy, a bottle of the juice and maybe even a package of Key lime cookies.
5 Visit Mallory Square
Join the sunset crowd at Mallory Square on the edge of the Gulf of Mexico at dusk. First browse the carts where vendors hawk everything from beaded jewelry to primitive artwork and signs with island sayings, like “It’s Five O’clock Somewhere.” Second, catch street performer Will Soto’s balancing act as he jungles and walks the tightrope. Third, snap a few selfies with the flaming golden orb in the background.
6 Hang with the Locals
Put these drinking stops on your list. Local dives, like the Green Parrot where regulars claim the same bar stool and island musicians know how to keep the party going, and Hog’s Breath Saloon whose reputation for serving stiff drinks is reason enough to go, will give you a different perspective of island life.
7 Take an Eco-Friendly Bicycle Tour
Book a spot on Lloyd’s Tropical Bike Tour for an off-the-beaten-path experience. Away from the tourist hub, you’ll explore tree-lined streets and stop to smell the flowers. Guide Lloyd Mager entertains with his conch shell music, and sampling freshly picked tropical fruits like mango, carambola and coconut water, along with stops to meet cockatoos and iguanas, are on the itinerary.
8 Snap a Photo at the Southernmost Point
Although it’s the quintessential tourist thing to do, having your photo taken at the red, yellow and black Southernmost Point marker, a concrete buoy mounted on the edge of the Atlantic Ocean, is proof you really are in Key West. The best time to visit the monument is at sunrise when crowds are almost non-existent and the morning sky provides a gorgeous backdrop. At this point, Key West is just 90 miles from Cuba.
9 Study the Architecture
Take a self-guided walking tour of Old Town to admire the historic architecture, predominantly wooden buildings dating from 1886 to 1912. Find Bahamian settlement homes and gingerbread-dripping Victorian styles. The Old Island Restoration Foundation provides a comprehensive walking guide to historic Key West on their website (oirf.org).
10 Raise Hell at Fantasy Fest
October’s Fantasy Fest is the event to attend for a full dose of the zany energy that thrives on Key West. Outrageously daring costumes, wild street parades, burlesque stage shows and even a clothing-optional body painting soiree bring folks of all sorts together during the 10-day festival. Just be sure to bring fantasy clothing and makeup; the official website even provides ideas and links to costume shops.