To most, the words “Key West” will likely bring visions of palm trees, sunsets, margaritas and lost weekends to mind. At only 2 by 4 miles and barely hanging on to the 120-mile long island chain known as the Florida Keys, this island oasis is one of the most coveted destinations in the United States. Forbes proclaimed it “one of the most sought-after destinations on the planet” while CNBC echoed those sentiments by calling Key West “among the top places to see in America.” This tiny island nation dubbed the “Conch Republic’” packs a wallop when it comes to unabashed natural beauty, water activities, dining, shopping and attractions. Travelers of all types satiate their wanderlust here from eco-tourists, adventure lovers, romance-seeking couples, family time bounding vacationers, and solo travelers looking for off-the-grid authenticity. Since a Key West vacation is literally a must do for your bucket list, we’ve compiled a great guide to get you on your way to an unforgettable experience full of memories guaranteed for a lifetime.
Dry Tortugas National Park
For an out of this world experience, travel a bit further south to the Dry Tortugas National Park aboard the official National Park Ferry, Yankee Freedom III, and travel even further south to visit Fort Jefferson
Ft. Jefferson-Dry Tortugas National Park is a place dreams are made of. A colossal, coastal fortress surrounded by untold miles of fantastically blue gulf waters is the first thing that grabs you. There’s the delicate, sandy shoreline that leads to undisturbed beaches, a sky that goes on forever and a vibrant, endless array of the most spectacular marine life you’ll ever see thriving beneath it. Want to make this dream a reality? Climb aboard the Yankee Freedom III for a voyage to the center of adventure. This state-of-the-art, high-speed catamaran is the preferred way to transport yourself to an awe-inspiring oasis that lies just 70 miles west of Key West. Snorkel the shallow reefs, bird-watch, lie out on a secluded beach or take a tour of what was once the largest maritime fort in North America. By the way, Condé Nast Traveler has named the Dry Tortugas National Park “one of the most beautiful places in Florida.” They’re totally right.
El Meson de Pepe
Cuban cuisine crafted by family tradition with some Key West flair
For an authentic Cuban meal just steps away from the waterfront at Mallory Square, look no further than the family-owned and operated restaurant El Meson de Pepe. Enjoy ropa vieja with plantains, rice and black beans along with a frosty mojito at sunset as the melodies of the live salsa band whisk you away to island paradise. In addition to beloved Cuban staples, El Meson’s chef likes to add a little flair to the more traditional fare like tossing chicken wings in a garlic mojo sauce and riffing on classic nachos by adding ropa vieja (shredded beef) and picadillo (Cuban-style ground beef). You may even be tempted to head to Spain and sample the delicious Camarones al Ajillo. A relaxed evening here is one of the best ways to enjoy the island’s famous Sunset Celebration in style! Live music fills the air on the weekends and be sure to explore the inside to see the story of the founder and his history through colorful cutouts on display.
Fury Water Adventures
Experiencing the local waters of Key West has never been this much fun
For over 20 years, this Key West company has helped visitors make lasting memories with their awesome water adventures. Though it may sound cliché, there is literally something for everyone with their many trip varieties. If you’d rather have an emphasis on relaxation and leisure, you can opt for a glass-bottom boat cruise or watch the ocean soak in the sun as you drink glasses of bubbly on a chill-axing Key West Sunset Cruise. If you need a shot of adrenaline, Fury’s got you covered with their Ultimate Adventure – the ones Forbes calls an “exhilarating, can’t miss adventure.” – which includes parasailing, jet-skiing, reef snorkeling, and a trip out to their floating water park. The glorious blue waters of the Florida Straits and the Gulf of Mexico surround this island and Fury knows how to show you a good time on the water in a fun, safe, eco-friendly way.
Old Town Trolley
Take in the island by land with a tour that has been delighting guests for over 30 years
The venerable green and orange trolleys have consistently ranked as one of Key West’s top attractions for over 30 years and for good reason. With the single largest fleet in the city, you’ll spend less time waiting and more time sightseeing. The friendly, knowledgeable conductors will take you on a fully narrated journey filled with humor and history as you explore the Conch Republic’s must-see sights. A really handy, time-saving component built into this tour is the freedom to hop on and hop of at any of the 13 stops they service. This means you can take as much time as you like strolling along famous Duval Street with its plethora of bars and restaurants then continue your journey when the next trolley shows up. This entertaining spin through the heart of sunny Key West includes highlights such as the historic waterfront, Simonton & Green Streets in the city’s Old Town, Bahama Village, and the East Martello Fort to name just a few.
Conch Tour Train
Don’t let this train pull out of the station without you
The world-famous Conch Tour Train is another great way to explore the folksy charm of the Conch Republic! Hop on board and sit back and relax as your tour guides whisk you away through the streets of Old Town to explore the haunts and old stomping grounds of the many colorful casts of characters that have called this island city home. See the home of prolific writer and raconteur Ernest Hemingway and experience the Conch Republic’s charm that has inspired the melodies of Jimmy Buffett biggest hits. And yes, this tour is complete with a smokestack, whistle and a cheerful conductor.
Truman Little White House
This winter white house is Florida’s only presidential museum
In 1946, Harry Truman began visiting Key West for rest and relaxation and loved it so much he and returned for 175 days during his presidency. In addition to President Truman, the home has played host to several other domestic and foreign heads of state including President Dwight Eisenhower, President John F. Kennedy, and British Prime Minister Harold MacMillan. A tour of this inspiring and historical piece of architecture is a must do when you’re in the Keys. With tours happening throughout the day, it’s easy to visit this museum and the knowledgeable guides give you glorious heaps of information as you peruse from room to room which has been restored to the Truman era.
Savor the flavors of old Key West at Fisherman’s Café
Before you get any bright ideas to venture out on an empty stomach, stop by Fisherman’s Cafe and get hooked on this Key West favorite
This is a must do first stop to start your day in the tropics just right. Dubbed “a paradise for serious foodies,” by Forbes, this local favorite, nestled in the heart of the Historic Seaport, serves fresh seafood, made-to-order specialties, and offers guests an authentic vibe that pays tribute to Old Key West. Visitors and locals have a serious addiction to this dive’s incredibly fresh, sustainable seafood and ginormous breakfast burritos. All menu items easily have out-of-this-world flavor combinations that include some of the very best grab and go handheld foods you can get on the island. The days catch is taken right off the boats nearby and prepared with passion by a local chef and combined with only the freshest ingredients available from local Florida farms and even their own grown herbs and spices. And, coffee lovers, on the way out, order up a Bucci. It makes you go zing. You can thank us later.
Key West Aquarium
Key West’s first attraction is still a shining star for visitors & locals alike
The hands-on Key West Aquarium is a great place to experience the fantastic, indigenous marine life that inhabits the offshore ecosystem. This window of discovery enables visitors to interact with rays, sharks and other sea creatures while expert guides explain the hidden mysteries of the undersea realm surrounding the Florida Keys. You can hold a starfish, see nurse sharks and get up close to numerous other aquatic species like moray eels, barracuda and sea turtles without getting wet. The welcoming Key West Aquarium is a popular attraction where nature and animal lovers of all ages can learn about the marine inhabitants and their incredibly biodiverse habitats.
Key West Shipwreck Museum
Sunken treasure, genuine silver and more on display as you explore Key West’s maritime heritage
Right across the way from the aquarium is the history-rich Shipwreck Museum. Feel the exhilaration as you climb 65 feet in the air to the top of the observation tower for panoramic views of Key West. Inside, find out how those who made their living off shipwrecks in the 1850’s watched and waited for ships sinking off the coast in Key West. Discover the true dangers of the era of shipwrecking and how it made Key West the wealthiest city per capita in the United States. Through actor presentations, exhibits, laser shows and collections of artifacts and treasures from actual shipwrecks, visitors can venture back in time for a glimpse into the history of the shipwrecking industry. It’s an ideal “voyage” for adults and children.
The most famous square in Key West packed with food stands, shops & performers
Located on the southern tip of the island, in the heart of Old Town, this large, waterfront plaza is a huge draw and declared “among the top places to visit in Key West” by Thrillist. You’ll find this place filled with street performers, musicians, several shops like the Sponge Market and Shell Warehouse to pick up some one-of-a-kind Key West souvenirs and an influx of people coming and going on the many cruise ships that enter into the nearby port. There are several restaurants nearby (like the aforementioned El Meson De Pepe.) Don’t forget to swing by the Conch Fritter stand to enjoy the official dish of the island! For a refreshing smoothie or key lime pie on a stick, there is a convenient Juice Bar stand right in the middle of the action.
The ideal place to see the world famous Key West sunset
This is also the place, as designated by locals, that traditionally hosts the daily Sunset Celebration, an event that makes for a festive evening by the water. The square is used to not only used to throw special events throughout the year but is also within close proximity to 8 of Key West’s top resorts. Here are a few other places worth visiting while in Mallory Square.
Key West Vacation Homes
Your home away from home with week-long or monthly rental options
Chic decor. Luxury appointments. Panoramic views. This is what you can expect when you indulge in the very finest accommodations for your stay in paradise. Breathe in the air of exclusivity and pamper yourself silly in these posh island digs that offer a wealth of options from white glove service, immersive pools, private boat slips, open floor plans, and amazing waterfront views. Whether it’s for an extended weekend getaway or an entire month, this is exceptional vacation living in some of the most desirable vacation homes in Key West.
Little Island with Lots of Punch
Key West may be a little island hanging at the end of the chain of the Florida Keys, but it is not short on the number of things you need experience in this lifetime. From southern-charms to eclectic events, it really is a whole new world once you step into the Conch Republic. Make sure you plan a Key West adventure to explore this unique space on our amazing planet so you can add a check mark next to this special once in a lifetime moment on your bucket list.