Hidden Gems of Key West

An island of only eight square miles, you might think Key West is a pretty easy place to navigate and understand—and it is! But just off the beaten path, it’s filled with hidden gems ripe for discovery. There’s a wealth of experiences to be had in Key West, from water sports to nightlife to arts and culture. To paraphrase famed poet Robert Frost, a former Key West resident, the road less traveled here can make all the difference.

Fort Jefferson & Dry Tortugas National Park

While you could certainly embark on a short trip to the coral reef just seven miles offshore in Key West, why not make that a whopping 70 miles and cruise west to the Dry Tortugas? You’ll pass uninhabited islands on your way to one of the most unique sights Key West has to offer. Tour the fort and learn about its unique history and snorkel through pristine waters on this unparalleled day trip.

Southernmost House

Easily the prettiest building in Key West, the iconic Southernmost House is a quiet bed and breakfast at the end of Simonton Street. A mansion made of pink bricks with sea foam cornices and a wraparound portico, it houses a quaint historic museum and oceanfront bar for the public to enjoy on a daily basis.

Sandbar Hopping and the Mangroves

A favorite weekend activity for locals is heading to one of the Gulf of Mexico’s sandbars or mangrove islands. Snipes and Boca Grande are the most popular. Pack a cooler, charter a boat and see for yourself! Or join Fury Water Adventures on the Island Adventure Eco Tour to relax in the shallow, warm, salty waters at Woman Key’s sandbar and kayak through clusters of the salt-tolerant mangrove trees.

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Bahama Village

Want to shop and dine at some of the hippest, locally owned spots in Key West? Then you have to head to Petronia Street in Bahama Villlage. Always a fascinating neighborhood on the fringes, it continues to up its cool factor year after year. For a casual breakfast or lunch, hit up Blue Heaven or La Creperie. One of the best dinners on the island? Spanish tapas at Santiago’s Bodega. There’s also an awesome collection of boutiques, like Besame Mucho and Wanderlust.

The Tropic Cinema

Need a break from the heat? How about a nice, dark, air-conditioned movie theater? This small Art Deco art house cinema screens independent films, documentaries and foreign films, as well as critically acclaimed blockbusters in the heart of Old Town on Eaton Street. Best of all, there’s no price gouge at the concession stand and they sell wine and beer.

The Porch & The Other Side

This duo of bars specializing in craft beer, fine wine and artisanal cocktails is tucked away inside a historic mansion off Duval Street. Co-owner Chris Shultz is the author of the popular book Quit Your Job and Move to Key West and his bars draws an eclectic local following. On any given night, you might find costumed burlesque performers, local boat crew, tourists and others mingling together on the sometimes peaceful, sometimes raucous front porch.