In Key West
Key West has a surprisingly quirky and fascinating history that lives on today in historic sites and attractions around the island. Once the summer retreat of President Harry S. Truman, his Little White House has been preserved as a museum and event space inside the picturesque Truman Annex residential neighborhood.
Perhaps the most famous Key West resident was Ernest Hemingway who spent most of the 1930s living in a home on Whitehead Street with his second wife Pauline. Today, The Hemingway House is a museum dedicated to the author’s life and his time spent on the island.
Henry Flagler’s Overseas Railroad, completed in 1912, played a significant role in the development of Key West as a vacation destination. In 1920, Flagler’s Casa Marina Resort opened its doors on New Year’s Eve and would go onto play host to such distinguished guests as President Warren G. Harding, Rita Hayworth and Gregory Peck. Spanning six and a half acres, the resort is still one of the most sought after on the island.
The Southernmost House is another eye-catching historic hotel. Located at the foot of the Atlantic Ocean, this 18-room Victorian Mansion is recognizable for its flamboyant turquoise and coral façade with porticos, bay windows and a proud turret.
For a taste of Old Key West, a stroll along the Historic Seaport is the perfect way to take in the marina where everything from fishing skiffs to mega yachts dock. It’s a great place to enjoy happy hour at one of the famed watering holes like Schooner Wharf.
The Dry Tortugas dates back to the Age of Exploration when Ponce de Leon discovered them in 1513. He also spotted hundreds of sea turtles (tortuga means turtle in Spanish) in the water, which is how the Dry Tortugas got its name. Found 70 miles west of Key West and home to the historic Fort Jefferson, the destination can be accessed by the Yankee Freedom III for day trips.
Perhaps Key West’s greatest draw is the scenic views available at every turn. To take in the beauty, head to the Southernmost Point buoy where you can gaze south across the Atlantic or for a gorgeous day at the beach, head to Smathers where you can enjoy sun, sand and surf.
The exclusive Sunset Key, accessible by a 15-minute ferry ride, is home to Latitudes restaurant, which is a privileged perch for dinner reservations at sunset with spectacular views. Mallory Square is the classic spot for taking in the sunset. Home to the nightly Sunset Celebration, street performers entertain a crowd in front of the most beautiful backdrop orchestrated by Mother Nature. Nearby, you can scale Shipwreck Lookout at the top of the Key West Shipwreck Museum for a bird’s-eye-view of the island.
If you’re traveling with the whole family or if you’re simply a nature lover, then don’t miss the Key West Butterfly & Nature Conservatory or the Key West Aquarium. You’ll immerse yourself in creatures fluttering in the air, crawling on the land and swimming under the sea.
For a more adult experience, Duval Street is home to more bars and restaurants than we dare count. Stop by iconic spots like Sloppy Joe’s and Margaritaville or head to Upper Duval for a more sophisticated side of the raucous street. Here, you’ll find art galleries, boutiques and fine dining restaurants.
Half of the pleasure of being in Key West is found offshore in the waters of the Gulf of Mexico and Atlantic Ocean. That’s where Fury Water Adventures comes into play with a smorgasbord of excursions including snorkeling, jet skiing, parasailing, sunset sailing and combo packages. The island’s calm, tranquil waters also make it ideal for a kayak or paddleboard outing with outfitters like Lazy Dog at the Cow Key Channel.
To get the lay of the land onshore, nothing beats a whirl on the Conch Tour Train where you’ll traverse the island learning about its history, architecture and points of interest. And, of course, the best way to get around Key West is by bicycle whether you rent your own or embark on a Paradise Bike Tour.
Key West is heaven for foodies with a slew of both casual and fine dining restaurants turning out crave-worthy dishes. Try classic spots like Blue Heaven and Louie’s Backyard for a true taste of Key West to go with your pan-fried yellowtail snapper.
For a modern gastropub, 2 Cents is one of the most popular new creating inventive plates like the “quack quack” nachos made with duck confit and bacon wrapped jalapeno poppers, while Garbo’s Grill offers Korean BBQ and shrimp tacos from an airstream parked in the backyard of a cozy bar off Caroline Street.
For Cuban food, head straight to El Meson de Pepe and indulge in ropa vieja (shredded beef) with black beans, yellow rice and plantains. The views overlooking Mallory Square are a bonus.
Two Friends offers a more casual, diner-like menu with plenty of fresh fish in an open air setting in Old Town. And for foodies looking for community, Isle Cook is a destination for cooking lessons, wine education events, demos and chef tasting menus with a cult local following.
Up the Keys
Of course, the scenic views start as soon as you embark on the Overseas Highway in the Florida Keys and one of the most awe-inspiring portions of the trip is crossing the Seven Mile Bridge, a floating bridge that is literally seven miles long connecting Marathon to the Lower Keys. Another stunning sight is Bahia Honda at Mile Marker 37 where portions of the historic Overseas Railroad extend past a lovely cove beach and park that’s ripe for exploring.
For your chance to swim with dolphins and learn more about these playful aquatic mammals, make a pit stop at the Dolphin Research Center at Mile Marker 58. In Key Largo, John Pennekamp Coral Reef State Park is not to be missed for snorkeling at the Molasses Reef and Christ of the Abyss, a statue of Jesus submerged 25 feet underwater.
If you get hungry on your trip up the keys, swing by Islamorada Fish Company for anything from conch fritters to blackened grouper sandwiches and mahi-mahi filets or Mangrove Mama’s at Mile Marker 20 for hearty sandwiches like the Philly cheesesteak or a fried lobster Reuben in a quirky, colorful, diner-like setting.