Mallory Square

Mallory Square: Our most recommended tours and activities

Key West Conch Train Tour

1. Key West Conch Train Tour

Climb aboard Key West’s conch train for a 90-minute sightseeing tour of the tropical paradise. The train departs from Front Street Depot and loops through the Old Town to end back behind the Depot at Mallory Square. Stock up on ice cream and homemade fudge at the Depot to eat on board during your tour. You can jump off at Truval Village to visit the Ernest Hemingway Home and Museum, Key West Lighthouse, Southernmost Point, and Key West Butterfly and Nature Conservatory. Climb to the top of the observation tower at Key West Shipwreck and Treasures Museum. Travel back in time to the days of hand-rolled cigars at Mallory Square. And stroll through the Cayo Hueso y Habana Historeum. Back on the conch train, learn about Key West characters, such as Mel Fisher, whose lifelong search for 2 sunken Spanish galleons finally turned up treasure worth USD 450 million. Jump off to enjoy great shopping on Duval Street, and fine dining at restaurants such as Hog's Breath Saloon, Jimmy Buffet's Margaritaville or the Hard Rock Café.

From Miami: Key West Bus Tour

2. From Miami: Key West Bus Tour

Embark on a full-day tour of Key West from Miami. Feel the Caribbean atmosphere of the Florida Keys and explore at your own pace. See important sites, including Hemingway’s House, or opt to swim in the sea. Start with a 4-hour drive across 43 bridges and 31 islands to America's “Caribbean Islands,” the Florida Keys. The string of islands and islets, bordered by the Atlantic Ocean and the Gulf of Mexico, leads to Key West, the only frost-free city in the continental United States! Once in Key West, experience a Caribbean atmosphere complete with friendly street artists, lively outdoor cafés, and alfresco restaurants. Spend some time exploring Key West on your own. Book lovers might like to visit Ernest Hemingway’s House to see the former home of the famous author. Or, if you prefer, you can go to the southernmost point of the continental United States at the famous "90 miles to Cuba" Monument. Explore museums, such as the Mel Fisher Museum, the Light House Museum, or Ripley's Believe It Or Not Museum (tickets not included). Feel the pulse of Key West at Mallory Square next to the cruise ship port. You may also choose to add one of our most popular adventure activities, such as a snorkeling trip to see tropical fish, a ride in a glass-bottom boat, or the hop-on and hop-off sightseeing trolley bus (tickets not included in the price). Depart Key West at 5:30 PM for the drive back over the bridges and islands.

Key West: 3-Hour Guided Bicycle Tour with Key Lime Pie

3. Key West: 3-Hour Guided Bicycle Tour with Key Lime Pie

Meet your friendly guide at the local partner’s office and get kitted out with your bike gear. After a short safety briefing it's time to head out on your island paradise adventure to see the very best that Key West has to offer. The first stop of the tour is the iconic Mallory Square, home to a popular nightly sunset celebration. Here, learn about the island’s history of smuggling and the shipwrecks that have crashed on the nearby reef. Next, pass by the presidential gates that lead to Harry Truman’s Little White House, which is known to have been his favorite vacation spot. Continue the tour onto Mile Marker Zero, which is quite literally the end of the road in the USA, then stop outside Ernest Hemingway’s former home where the famous writer penned many of his treasured novels. Head to the Southernmost Point in the Continental USA for a photo opportunity, then complete your circuit of the island as you ride past Higgs Beach, the White Street Pier, the Key West Cemetery, and the historic Seaport. At the end of an unforgettable 3-hour tour, enjoy a well-deserved rest and a slice of traditional key lime pie, an absolute must for any visitor to the island.

From Miami: Key West Full-Day Trip with Glass Bottom Boat and Transfer

4. From Miami: Key West Full-Day Trip with Glass Bottom Boat and Transfer

Getting to Key West from Miami on your own can be a daunting task, but this trip includes round-trip transfer so you can spend less time worrying and more time enjoying. When you arrive at Key West, you’ll have plenty of time to explore the area alone before taking the glass bottom boat out onto the water. Beloved by tourists and locals alike, the area is known for its idyllic Caribbean waters, good weather and stunning beaches. During your free time, explore all that Key West has to offer. There are plenty of interesting and entertaining things to do including visiting the Hemingway House or Mallroy Square. Located by the historic waterfront, it is a place where many gather for a never-planned, always unique daily celebration. Then move on to the highlight of the day, the boat ride. The special boat features a transparent glass bottom which allows you to see one of the world’s largest reefs, home to a multitude of tropical fish and marine life.

Florida: Key West Overseas Highway Self-Driving Tour

5. Florida: Key West Overseas Highway Self-Driving Tour

Begin your sunshine-filled journey just an hour outside Miami, Florida: on Key Largo. Start the scenic 100-mile drive bypassing the ‘African Queen’, the iconic Hollywood riverboat. Follow in the historical footsteps of the Overseas Railroad to Plantation Key, the smuggler's haven. While there, check out Big Betsy, the giant lobster, and Theatre of the Sea, home of the original dolphin shows. Continue through Isla Morada while learning about the hurricanes, ecosystems, and wildlife of the tropical Florida Keys. Explore Anne’s Beach, Long Key, and Marathon, each of which contains unique attractions. Cross over the iconic Seven Mile Bridge and make sure to check out Fred the Tree, the famous spirit of the Keys. Journey past Pigeon Key and Geiger Beach until you reach the most famous Key of all: Key West. In popular Key West, discover Mallory Square, Truman’s White House, the Hemingway Home, Tennessee Williams’ House, and the historic lighthouse. Wrap up your tour at the Southernmost Point of the Continental US.

Key West: Private Tiki Boat Sunset Cruise

6. Key West: Private Tiki Boat Sunset Cruise

Come with your friends or family for an unforgettable experience on a private tiki bar boat cruise in Key West during sunset. Enjoy your own food and drinks as the sun sets over the picture-perfect scenery. Toast to the sunset with your favorite drinks in hand and keep an eye out for the green flash as the sun meets the beautiful Caribbean water. Cruise past the world-famous Mallory Square and then just beyond Sunset Key to find the best vantage point. Your captain will point out all the sites as you cruise around the harbor and eventually return to the Historic Charter Boat Row.

Key West 2.5-Hour Urban Adventure Quest Scavenger Hunt

7. Key West 2.5-Hour Urban Adventure Quest Scavenger Hunt

If you’re looking for a way to turn Key West into a giant game board, Urban Adventure Quest has created an interactive scavenger hunt that combines the fun of the Amazing Race with a 2.5-hour sightseeing tour of Key West. Guided from any smart phone, teams make their way around the well-known and the overlooked gems of the city, solving clues and completing challenges while discovering Key West’s art, culture, and architecture. Race to be the first to finish the game, or take as much time as you need, solving clues, completing challenges, and learning about local history along the way. The adventure begins at the Historic Seaport and takes you on a well-designed course down Duval Street, in and around Mallory Square, and through a famous cemetery and other unique sites. The tour involves a bit more than 2 miles of walking. Using a smart phone as your guide means that you can start when you want and determine your own pace of play. Stop for a burger in paradise or a slice of key lime pie – you’re on your own schedule! Offered at a fixed price for a group as opposed to per person pricing, this city tour/game is a great value for those on a budget.

Key West: Self-guided old town treasures walking tour

8. Key West: Self-guided old town treasures walking tour

Find out why Key West attracted so many cultural legends on a self-guided walking tour of the quirky old town. Starting from Mallory Square, follow the precise directions of your audio guide mobile app to learn the fascinating history behind the people and places that make the island so special. Starting from the Memorial Sculpture Garden in Mallory Square, you’ll discover the stories behind Key West’s most famous sights, including the residence of former President Harry Truman, Florida’s oldest bar, the hotel where Tennessee Williams stayed for ten years and the so-called longest street in the world. Along the way, you’ll learn how salvaging shipwrecks transformed the city, why the buildings’ aesthetics are so strictly controlled, how the city became known as the ‘Conch Republic’ and why there are so many chickens running around.

Available activities

  • Guided tours
  • Day trips
  • Adventures
  • Water activities
  • Other experiences

Other Sightseeing Options in Mallory Square

Want to discover all there is to do in Mallory Square? Click here for a full list.

What people are saying about Mallory Square

Overall rating

4.2 / 5

based on 390 reviews

It was a great experience! The trip was pleasant and the itineraries were fully fulfilled. The guide very nice and entertaining to give the information. He guided us with efficiency and sincerity so that time would reach us to get the most out of the tour.

Our super friendly Daniela, full of information. On the other hand, no or very little air conditioning… hard after a day of walking in the stifling heat

The app was very easy to use and very helpful. I would recommend using this app to learn about the area and the sites to see.

The tour was great! Tamara and Frank was gently. Route to Key was fast.

the place is beautiful and is worth the long ride.