Mallory Square

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Mallory Square: Our most recommended tours and activities

Miami: Day Trip to Key West with Optional Activities

1. Miami: Day Trip to Key West with Optional Activities

Start your day on an air-conditioned bus from Miami Beach to Key West with a 4-hour drive. Watch as your tour guide points out the famous 31 Caribbean Islands along the drive known as the Florida Keys. Cross 43 bridges as you travel through the Keys to Key West. See the Atlantic Ocean and the Gulf of Mexico while driving by the coastline. Key West is the most southern point of the USA and only 90 miles from Cuba. Once you arrive in Key West, get 6 hours to explore the island at a leisurely pace, stroll the artistic streets, or relax at outdoor cafes and restaurants. Upgrade your day trip by choosing an option that includes one of the following inclusions: - Hop-on Hop-off Conch Train All-Day Ticket with an included ticket to the Sails to Rails Museum. This 70-minute narrated tour around Key West is one of Florida’s Top attractions, covers over 100 points of interest, and includes 4 Hop-on Hop-off stops around town. - A 3-Hour snorkeling adventure at North America’s only living coral reef. Travel on a state-of-the-art Catamaran, receive professional instruction, use top-of-the-line snorkel gear, and enjoy an open bar on the way back (including sodas beer, wine, champagne, margaritas, well-mixed drinks)  - A 2-Hour cruise on a glass-bottom boat where you can witness the wonders of North America’s only living coral reef, maybe spotting sea turtles and rays. Fun for all the family, you also get great views of Key West from the sea. - A 12-15 minute parasail off the coast of Key West on a 1-Hour parasailing adventure. Enjoy the tropical vibe of the Keys as you are helped into your parasail harness, before being slowly raised in the air, until you are flying high above Key West. Make your way back from Key West to Miami Beach at 5:00 PM.

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 Conch Train Tour

3. 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.

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

4. 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.

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: Self-guided old town treasures walking tour

6. 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.

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.

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 349 reviews

the bud was late in the morning but it was super fine. the drive was very good we slept and only woke up to the scenic bits. we didn't feel like there was enough hours there in the day to explore! so much to see! everyone was so friendly would recomend spending the night there if possible. very charming town we bought activities such as the key west train separately with get your guide so was cheaper. definitely bring physical money to tip ! the beach was amaizing. we took uber to the places the train didn't stop at but if u can rent a golf kart I think would be good or bikes. plenty of bars with music we had the best homemade Italian ice cream as well- absolutely lush. the drive back was peaceful but the toilet on the bus was unkempt but this is to be expected so bring your own toilet roll and spray

Our guide, James, was very knowledgeable and engaging. He reached out to each member of the group to make sure everyone was having a good time. The leisurely pace made it very relaxing.

The tour has 4 convenient stops, and was very informative about some if the island’s history. The guide was very entertaining. I would recommend this tour for anyone visiting Key West.

App worked as expected and gave a great overview of sites as we approached them. Offered good suggestions on places to stop along the way.

Long ride down but better than driving ourselves and cheap for the distance