Mallory Square Tours

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.

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.

Ride through the streets of Old Town Key West during a leisurely bicycle tour—a perfect introduction for first-time visitors. Learn about the island's history and see highlights such as Mallory Square, Mile Marker Zero, and White Street Pier. Pedal out to the Southernmost Point Buoy and enjoy panoramic ocean views. Plus, choose from morning or afternoon times to easily fit this tour into your schedule.

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.

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.

From local shrimp to the perfect Key lime pie, Key West dining is a food-lover’s dream, but finding authentic flavors can be a challenge in a town packed with touristy restaurants. Discover the very best bites on a gourmet tour that samples a little bit of everything, exploring Key West’s charming neighborhoods, colorful characters, and history along the way.

Take in the views of Key West from above on this scenic, small-group helicopter tour. Circle 20 miles (32km) around the island, passing over popular landmarks including Smather’s Beach, Fort Zachary Taylor State Park, Sunset Key, and Duval Street. Find a time that works best for you with convenient departure times offered throughout the day.

This is the only 2 hour sunset cruise in Key West that provides a private guided tour around the island.Sit back and relax while your Captain points out all the sites along the way. Enjoy the privacy of a private charter. Feel free to bring food or beverages of your choice. Price is $375 TOTAL and includes up to 6 people. Looking forward to seeing you on the dock!

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.

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.

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.

While there are a number of catamarans to chose from in Key West, Bimini charters is unique in that we limit the number of people on our public cruises to six, so you can have a comfortable and safe sail distanced from others with much room to spread out, unlike other charters where they jam over 20 people in the boat with you. We also allow you to bring your own drinks and food so that you can create your own memorable experience with the food and cocktails that you prefer. You can also rent the entire boat out for 1/2 day (3 hour) or full day (6 hour) sails to host family and friends on a private charter (up to 10 people.) The S/V Liberty is a luxurious 44-ft cat, offering 5 different seating areas, so you can spread out, enjoy different vantage points, and savor the coastline as we sail by. Enjoy a romantic sunset cruise, host a cocktail party, all aboard this luxurious yacht.

Stroll along the Gulf of Mexico, enjoying the island’s best happy hours, then watch the famous Key West sunset. Download this multi-media, GPS-driven tour to your phone or tablet. It's like walking with your own local tour guide! Historic photos, recordings and videos plus links to restaurant menus and websites rest at your fingertips. In just 35 minutes of walking, you can cool off at a tiki bar with a gorgeous waterfall, then stroll along a hidden boardwalk with stunning ocean views. Find the best best happy hours with the tastiest seafood snacks. Stroll past Jimmy Buffett’s secret recording studio. Enjoy Key West’s most popular brewery, best mojito, or the world’s yummiest coffee. Learn where locals watch the sunset. Sight-see at your own pace, avoid being herded in a crowd, and linger only in the places that truly interest you. After purchasing, check your confirmation emails for instructions on how to download your tour to your phone or tablet.

Key West is famous for it's sunsets and it doesn't get any better then on a private sunset cruise aboard our custom tiki bar catamarans. You and up to 5 guests will toast the sunset with your favorite libation(BYOB). Our boats feature a large thatch roof for shade, bluetooth tv and stereo, a walk in bathroom, adjustable padded bar stools and a gorgeous live edge tiki bar. You'll cruise the Key West harbor in style and view the famous sunset on your private 2 hour adventure.

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 and tuna poke 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!

Visit the one-and-only island city of KEY WEST! Enjoy a narrated tour on the way down, and island music on the way back. HIGHLIGHTS • See the sights in Key West • Stay for the Key West sunset • Plenty of Free Time • Designated Driver • Narrated Tour Do what you want in Key West! We're doing the driving! Choose to sightsee, enjoy a happy hour, eat a nice dinner, check out Mallory Square at sunset, take a sunset sail, and more! Sit back & enjoy the scenery as we drive down to Key West. We're licensed like a limousine, so you can enjoy your favorite beverages en route. Learn the history, culture, and ecology of the Florida Keys & Key West from your friendly local guide. See the Southernmost Point, Hemingway's House, Mile Marker Zero, Sloppy Joe's, and Mallory Square It's more like a road trip than a tour - ask questions, point out wildlife, make new friends.

Walk through Old Town Key West with a long-time local, see & learn about the unique places you can visit during your vacation. **If it's too far or too hot to walk, you have the option of hopping on the Duval Loop bus with your guide for only $1 per person** 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.

Enjoy a morning sailing experience and have Schooner America 2.0 all to yourself! Let us whisk you and yours away on a glorious morning sail across the beautiful waters of Key West on your own private yacht! This 1.5 hour charter aboard the America 2.0 grants you all the luxuries of yachting on your own private schooner. Let our crew do the work as you sit back and relax and take in the sights. Soda and water included. Alcoholic beverages and food are available for purchase onboard. Due to our licensing, guests are not permitted to bring their own alcoholic beverages on their sail. At this time, we do not offer swimming, snorkeling, or diving. After booking, you will be contacted by a Classic Harbor Line representative regarding more details about your trip.

A great way for families and friends to relax on Christmas morning! Enjoy a 2-hour sailing experience aboard the beautiful and classic Schooner America 2.0. Your ticket includes a special Christmas Day plated brunch served onboard including spiraled ham, bagels and pastries, meats and cheese, smoke salmon, crudite and more! Also enjoy complimentary beer, wine, Champagne, mimosas, bloody Marys and soft drinks. Sit back and relax as the crew raises sail and provides beverage service. As the boat sails along the majestic Key West waters, take-in views of Fort Zachary Taylor, Sand Key Lighthouse, Mallory Square and Sunset Pier.