Departing from Key West’s Historic Seaport, the Appledore Star’s sails are raised for an authentic sail experience on the way to Key West’s backcountry. Your day is spent exploring Key West’s uninhabited mangrove islands... More

Key West’s ONLY Happy Hour Sandbar Party & Sunset Cruise! Get ready for the ultimate Key West experience—the only Happy Hour at the Sandbar & Sunset Cruise! This exclusive trip takes you to a beautiful sandbar, where you can l... More

Escape the ordinary and embark on an unforgettable journey aboard our 50 foot sailboat, “Chao Lay”. Choose a 3-hour Day Sail or our popular Sunset Sail through the Florida Keys Marine Sanctuary in Marathon, Florida. Our sailbo... More

If you’re looking for the ultimate Key West experience, join the 'Duval Crawl' pub crawl! Key West is famous for its lively bars. Join the original Key West Pub Crawl established in 2002. The only pub crawl that includes five dr... More

These Tours are unique because they are offered by a seventh generation local who knows the waters and can take you to places other people can’t. This completely custom and private tour so start Band end times are charla e upon... More

We offer new Four Winns boats for the tour with maximum of 6 people, ensuring an intimate and fun-filled adventure for all. Our trips depart daily from The Perry Hotel. Tour times may vary throughout the year. For our guests wh... More

Trips are customizable - to a point. Your friendly, knowledgeable guide has experience with all sorts of ocean activities and knows the waters around the Lower Keys really well. So there are a few different areas to choose from on... More

The Hemingway Experience celebrates Key West’s most infamous author, Ernest “Papa” Hemingway, with a historical walking adventure retracing his steps on a "Bucket List" tour of Old Town. Our 4-hour guided experience stops at... More

Max 6 people. Explore the waters around Key West in the Looking Glass, our 28' glass bottom boat. This versatile boat let's you plan your own adventure. Snorkel the reef, explore an offshore island, look for dolphin and other mari... More

Enjoy the Thrill of the open sea and the comfort of top class amenities, ideal for sunbathing, sightseeing or simply relaxing with your group exploring with stops like Fort Zachary Taylor Historic State Park, U.S. Coast Guard Cutt... More

Come experience the Crystal clear waters and sandbar island surrounding the Florida Keys. This tour can be completely tailored to whatever you have in mind. From drinking and relaxing on the sandbars to a full eco-tour through t... More

Experience the best of Key West on our guided walking and boat tour, where you'll delve into the island's rich history and explore its stunning coastline. Begin your journey by strolling through the charming streets, learning abou... More

Experience the beauty of the Florida Keys, gorgeous turquoise water and abundant fish! Marathon the hub for fishing in the Keys, great beaches, shopping, and fantastic food. View the beautiful scenery, while experiencing the thril... More

Embark on an unforgettable journey in Key West, where laid-back vibes meet vibrant culture. Explore the island's storied past, from its indigenous roots to its role in pivotal historic events like the Civil War and the Spanish-Ame... More

We are owner-operated and ensure every detail of your trip is perfect! We work with you ahead of time to determine your goals for the day and make them happen. Our guests almost always say that their trip with us was the highlight... More

Please Note: Price of $695 is for up to 6 guests. Enjoy this private charter with friends or that special someone! Soak up the afternoon sun and cool off in the bright aqua waters of the Keys as you snorkel and explore Florida's a... More

Rent your own private yacht and savor the beautiful Key West sunset away from the crowds. Do it all on a luxury catamaran reserved just for you! Dolphin watch, jump off of the bows of the boat, sail along the Key West coastline, a... More

Rent your own private yacht and savor the beautiful Key West waters away from the crowds. Do it all on a luxury catamaran reserved just for you! Snorkel a pristine reef, dolphin watch, jump off of the bows of the boat, sail along ... More

Join in on the annual Wreckers Race and take part in a fast pace race toward Sand Key Lighthouse aboard Schooner America 2.0! Back in the day, pirate ships from afar often ran aground on Sand Key Reef, nine miles off the southern ... More

Experience the charm of Key West from a unique perspective with our Harbor Cruise. About Set sail from historic seaports and meander through picturesque harbors, where colorful sailboats and historic landmarks line the waterfront... More