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An island of only five square miles, Key West is a pretty easy place to navigate. It’s also filled with hidden gems ripe for discovery.
To paraphrase former Key West resident and famed poet Robert Frost, the road less traveled in Key West can make all the difference. And that’s exactly what you get when you hop aboard Old Town Trolley – the road less traveled far beyond Duval Street.
This is your guide to unlocking the hidden gems of Key West as you roll through town on your Old Town Trolley tour.
Feel free to hop off at any of the trolley stops, explore the surrounding area and hop back on when you’re ready.
On the far southeastern stretch of the island you’ll find East Martello Tower, a Civil War era fort built with eight-foot thick granite walls to withstand bombardment.
Although it never saw hostile action during the war, today it’s an off the beaten path point of interest for its historic architecture and its art collection. Home to wood carving paintings and drawings by Mario Sanchez that depict Old Key West, the tower is also rumored to be haunted. A visit here will reveal the spooky tale of Robert the Doll.
Strolling up tree-lined Whitehead Street, you might not even notice the Victorian-style historic home and garden that’s crawling with banyan trees, palms, orchids and bromeliads. The Audubon House & Tropical Gardens was named after famed artist John James Audubon who visited the home in 1832. Today, it houses 28 of his first edition drawings of the tropical wading birds that he discovered in Key West and the Florida Keys during his expedition.
While Key West was never a slave port, three slave ships heading for Cuba were intercepted by the US Navy in 1860 and the slaves on board were brought to Key West for care. Of the 1,432 African slaves aboard these ships, 295 did not survive in spite of the city’s best efforts. Their burial site is memorialized today near the White Street Pier on Higgs Beach.
Many Key West visitors know that a meal at Blue Heaven is a must; but few realize that Blue Heaven’s sister restaurant Salute! is another top dining option. Situated directly on Higgs Beach with an enormous covered patio and views of the sea, it’s one of Key West’s only true beach-front restaurants. It’s also one of the best places to order a sophisticated seafood dish and fresh Italian fare. A favorite on the menu is the sautéed yellowtail snapper in lemon cream sauce.
When it comes to an off-the-beaten path bar and restaurant, look no further than Garbo’s Grill at Grunts Bar on Caroline Street. This hidden gem is tucked away in what looks like a private house; but it’s actually a quiet little bar serving beer in frosty mugs. It’s also where you’ll find Garbo’s Grill, the cult classic food truck featured on Guy Fieri’s Diners, Drive-ins & Dives. Owned and operated by a local couple, they serve up everything from Korean BBQ to fish tacos to one seriously juicy cheeseburger.
You have to know what you’re looking for to find the Chart Room. This tiny dive bar found at the Pier House Resort is one of Key West’s oldest and saltiest dives. The walls are lined with nautical flags and old photographs; and the décor ranges from model ships to old barrels. Order a stiff drink and make yourself at home at this bar where not only popcorn, but peanuts and hot dogs too, are free.
The Southernmost House is easily one of the most recognizable Key West landmarks with its pink and sea foam Victorian architecture; but few realize that it also houses one of the island’s most beautiful pools – and it’s open to the public. For a mere $10 (that includes a free drink), non-hotel guests can access the zero-entry pool at this boutique bed and breakfast overlooking the Atlantic Ocean with lounge chairs and hammocks for optimal relaxation.
One of the best ways to experience the waters of Key West is on a sandbar or in the mangroves of the backcountry, just like the locals do. With Fury Water Adventures’ Island Adventure trip, you’ll spend the day snorkeling at little known reefs, relaxing on a shallow sandbar and kayaking through mangroves with barely another boat in sight.
Bahama Village is the ultimate hidden gem neighborhood in Key West. Wander down Petronia Street through this historic district for the hippest locally owned shops and restaurants. Blue Heaven is a classic at brunch time with surf and turf eggs benedict in a rustic outdoor setting. Santiago’s Bodega is a modern hit with Spanish-style tapas in an intimate dining room. And don’t forget to hit up Besame Mucho, a beautifully curated boutique, for the perfect Key West souvenir.
Many find Key West strange during the day; but after the sun goes down, the restless souls of the island’s frightful past begin to stir. You will hear their tales that have been all but forgotten as you travel the narrow, dark streets of Old Town – filled with 19th century wooden houses that hold on to the secrets of their former inhabitants. Stories so tragic, so chilling, you’ll see why Key West is one of the top ten most haunted cities in America. This and more await you on a Key West ghost tour.
Located on Elizabeth Street along the Historic Seaport, Fisherman’s Cafe offers a modern take on classic Old Key West flavors. Originally founded in the 1970s on Caroline Street, this walk-up eatery used to be the local hangout where fishermen came to swap stories and travelers learned the real history of Key West. Today, Fisherman’s Cafe holds true to its heritage as a laid back watering hole serving up just caught seafood, authentic Key West traditions and locally sourced ingredients. Start your day with a hearty breakfast sandwich and Cuban coffee or enjoy a fish sandwich and sweet potato fries for lunch as you continue sightseeing around the island. No matter which menu item you choose, you’ll be experiencing the flavors of a true Key West hidden gem.
Take your island exploration to new a new level with a boat rental. Be your own captain for the day and discover everything the surrounding Key West waters has to offer: unique Florida wildlife, one-of-a-kind views and memories that will last you a lifetime!