Mallory Square Tours and Activities

Watch the sun set and the moon rise off the coast of Key West on this sunset cruise. Enjoy the scenery and peaceful calm of a late afternoon sail aboard a 70-foot catamaran with plenty of deck space to stretch out and enjoy the breathtaking view. Then watch a legendary Key West sunset as the sun glistens and gently settles into the water. Hearty appetizers plus champagne, wine, full liquor bar, ice-cold beer and soft drinks are included.

Experience a sunset you’ll never forget on this 2-hour catamaran cruise in Key West. Sip on your choice of wine, champagne, beer or sangria as you watch the sun go down over the water. As you sail you’ll catch glimpses of the island and marvel at the views from the turquoise water. Cocktails are also available at a cash bar on board.

Enjoy the sunset from the water on this Key West cruise aboard a classic schooner. As you stand on the deck of the tall ship, pass by sights such as Mallory Square with its Sunset Celebration and the Navy Mole, where big ships dock. Hors d'oeuvres and unlimited drinks are included onboard. Take your pick of beer, wine, sparkling wine, cocktails, soda, and homemade tropical sangria.

Leave behind the crowds of Key West and catch a quintessential Florida sunset while enjoying drinks on a sailboat. There is no better vantage point for watching the sunset over the water than from the water itself. And, while larger sunset cruises can get overcrowded, this small group experience ensures you have a spot at the rail when it comes time to capture photos of the setting sun.

Explore Key West by land and water on a full-day tour with round-trip bus transport from Miami and a snorkeling cruise. Gorgeous scenery on the Overseas Highway to Key West means it’s best to let someone else drive, so you can just sit back and enjoy the view. After free time to explore Key West on your own, board a catamaran for a luxurious trip to a great snorkeling spot on the coral reef.

Getting to Key West from Miami on your own can be such a hassle, but this nearby city has so much to offer. Don’t miss out—this day trip includes round-trip transport from your hotel, so you can enjoy a stress-free ride without worrying about navigating through a new area. Plus, you’ll have plenty of free time to plan solo explorations, and multiple upgrade options are available for add-on activities.

Set sail on a replica of the 1851 Schooner America on a cruise from Key West. See the top sights of the city, including Fort Zachary, Mallory Square, and Sand Key Lighthouse from a unique perspective. Your cruise is accompanied by complimentary hors d’oeuvres along with alcoholic and non-alcoholic beverages. Allow yourself to truly unwind as the sun sinks into the Atlantic Ocean.

Explore the best that Key West has to offer on this narrated, Conch Train Tour. See Key West’s top attractions and learn about the Conch Republic’s history and residents, past and present. See where Ernest Hemingway used to hang out and find out why Harry Truman used to spend so much time here. Get to know Old Town Key West, from the Front Street Depot to Mallory Square and everything in between, including live onboard commentary from a professional tour conductor. It’s Key West’s original, and most iconic, sightseeing tour.

Set sail on the schooner Appledore for a scenic cruise from Key West!.  Join the crew to raise the sails, take a turn at the wheel, or just soak up views of the gorgeous Florida coast with a cocktail.. Choose a day sail for maximum sunshine, or opt for a sunset sail in the early evening, then enjoy a selection of drinks during your time on the water.

Enjoy the Caribbean vibe of Key West on this day trip from Fort Lauderdale. Enjoy comfortable round-trip bus transportation to this historic island city and wander at will, or choose from a variety of tour upgrades. Add a 90-minute Conch Tour Train or a hop-on hop-off trolley tour to see all the attractions. Or get out on the water and select from a 3-hour snorkelling adventure, a 2-hour glass-bottom boat cruise or a 15-minute parasailing ride. Pickup and drop-off from Sheraton Fort Lauderdale Airport and Cruise Port Hotel included.

Experience a slice of sailing history while soaking up fantastic Key West views on a cruise aboard the America 2.0, a replica of the schooner that won the very first America’s Cup. Relax on padded benches and teak decks as your captain navigates the island coastline past landmarks like Fort Zachary Taylor and Sand Key Light Tower, and sip unlimited drinks from the full onboard bar.

Our Captain’s Choice Dolphin Watch Sunset Sail is the ultimate VIP sailing experience! Limited to an intimate number of passengers, this 3 hour sail is more like a private cruise than a group tour and is one of the top things to do in Key West. As we leave behind the Historic Seaport, look for Key West landmarks like the legendary Mallory Square, opulent Sunset Key and historic Fort Zachary Taylor. On reaching open water, the sails are unfurled and your adventure begins as your captain tracks dolphin pods to provide you an up-close view of these elusive creatures. With the dolphin viewing over, your cruise is just getting started! Grab a drink and relax as your captain positions the luxury catamaran for the perfect view of a famous Key West sunset. A chef’s selection of Tapas including shrimp cocktail are served during the sail. Choose your favorite drinks, including boutique wines and champagne perfectly paired with our Tapas – all included in the cost of your tour!

Get ready for fun in the sun on this day trip and snorkeling adventure off the coast of Key West from Miami. Ride across 32 islands from Miami to Key West, explore the island city, then sail away on board a spacious 50-foot catamaran vessel. Jump into the water off the coast for a snorkeling session above a coral reef with 600 different species of marine life. Professional snorkeling instruction provided. Relax, feel the warm sea breeze and enjoy the day. Miami hotel pickup and drop-off included.

Key West is famed for its sunsets but the scene in town tends to be crowded. Sidestep the big crowds by getting out onto the water on a private tour. In the company of just your party and the captain, relax as you cruise around the island and the captain points out all the important landmarks.

Embark on a tropical adventure with this all-level snorkeling sail trip from Fort Lauderdale. Board a 50-foot (15-meter) catamaran and sail the Florida Keys’ crystal waters with expert guides who offer insight about the surrounding area. At the diving location, don your snorkeling gear and hop into the water to spot brilliantly colored coral and tropical marine life. You’ll also have plenty of independent time to explore vibrant Key West.

Enjoy the scenic and breathtaking drive on the Overseas Highway One passing Key Largo and the famous Seven Mile bridge to America’s southernmost city Key West. If you selected the snorkel tour option in Key West we will board a boat for 3 hours and go out to the reef where we will snorkel and experience Florida's underwater world. Beer, wine, margaritas and sodas are provided as well as basic snorkel gear. This is a tour ideal for snorkel beginners. After the snorkel tour you will have some time to experience the highlights of Key West on your own including the white Victorian conch villas and lush tropical gardens. Stroll along Duval Street with its cute shops, bars, galleries and cafes to the famous southernmost point monument located just 90 miles north of Cuba. Key West’s Caribbean flair and charm will seduce you and is a favorite day tour from Miami. Round trip transportation from select Miami meeting points is included.  

Cruise alongside Key West’s picturesque waterfront in style during this private sunset tour aboard a charactered tiki bar boat. Enjoy BYOB drinks in a floating, thatched bar, complete with private restroom, bluetooth-equipped television and stereo, and padded bar stools. Head past attractions like Sunset Pier, Mallory Square, Wisteria Island, and Trumbo Point, with cruises timed to capture the coastline’s famous sunsets.

Key West is famous for its sunsets. Rather than joining the crowds at Mallory Square, you can enjoy a more personal, uncrowded experience on this small-group sunset cruise. Aboard a custom tiki bar boat, you can toast the sunset (byob) while taking in the sights as you cruise around the Key West harbor.

Welcome to Key West! Stroll through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation. This is a private tour just for your group = we won't group you with others. Perfect for your wedding party, couples, family & friends, bachelor and bachelorette party, birthday party, reunion, corporate groups, and more! It's even fun for solo travelers! **If it's too far or too hot to walk, you have the option of hopping on the Duval Loop bus with your guide** It's air-conditioned with several convenient stops throughout Old Town. These tours are private so you can ask questions and we can customize the tour to your interests. Your tour guide is knowledgeable about everything Key West, so don't hesitate to let us know what interests you and what you want to know about Key West. Total distance about 1 1/2 miles.

Located more than 150 miles (240 kilometers) from Miami, Key West is a long day trip to make on your own. That’s why you need someone else to do the driving. This guided tour handles all the logistics, so you can relax and enjoy the views along the way and activities in Key West. Plus, the efficient tour provides ample time to explore before returning to Miami in the evening.

There's so many great places to eat and drink in Key West that it can be difficult to choose. Let this guided tour make the decisions for you. You'll stop into several locals' favorite restaurants to sample cocktails and food before heading to Mallory Square in time for the sunset celebration.

Discover Key West in a fun new way on this 3-hour scavenger hunt. Jump into the middle of an exciting adventure from the Historic Seaport at Key West Bight to Duval Street, Mallory Square and other real-life locations around town. Discover both well-known and overlooked locations, solving clues and completing challenges via smartphone while learning the local history of this popular island city. Teams of 2- to 5-people are welcome.

Looking for the perfect way to end your day? Join us on the Seabreeze and ride in comfort with this relaxing, catered cruise into the horizon on Key West’s gentle seas. Relax in the shade under the bimini or sunbathe on the bow to take in that last bit of sunshine. Sunset Cruises are a Key West luxury with our panoramic views of the sun melting into tropical waters – and the best way to enjoy it is with good food and great drinks! Departing from the Garrison Bight Marina, your sunset cruise will take you on a unique path away from the rush of boats leaving downtown. This exclusive cruise is a great way to start your night out, celebrate a special occasion, or bring your stay to a close with an easy-going route through the Key West Harbor and the Gulf of Mexico. We operate year-round at reduced capacity for a more intimate experience for our guests. You’ll get to know our crew and maybe meet some friends along the way. We also have a full marine head (bathroom) for your convenience.

We are the only floating bar on the island and we take you to places that normal tours do not, 100 year old Shipwreck, Movie boat set of Beach Bum, and we provide swimming, snorkeling, water saddles and Reef viewers. You will see Castaway Island a.k.a. Christmas Tree, Sunset Key and the crazy wildlife in, under, and around the waters of Key West. We also offer Sunset Tours. Join us from launching off the only downtown beach in Key West - Lagerheads Beach Bar. Our beach has a restaurant and drink. Along with live entertainment and lounge chairs for you to rent and stay all day. See you soon.