2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide" USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for t... More

Enjoy a yacht-day bachelorette trip where everything is already set to go right from the biggest and best marina in SOUTH BEACH... We've found the boats, brought on the food and drinks, and made sure that everything that a good y... More

This 2 hour sailing excursion may take place in Pensacola Bay, passing by areas of Sabine Island, Deer Point, Fair Point and Deadman's Island. We may also sail east under the Bob Sikes (Pensacola Beach) Bridge, exploring areas of ... More

One of the best ways to relax on your vacation is to view a sunset aboard Destin sailing Adventures. Sit back and relax while Captain Kip takes you to the best spots to view the sunset, and see a dolphin.... More

Enjoy some time on the water with this 6-Hour Full Day Sailing Charter located in Fort Lauderdale. Your sail is entirely customizable, and travelers have the option to use their time docked or sailing out to sea. Once on the water... More

Enjoy a private Sunset Sail on a Classic 60 ft Schooner Serenity and get a front-row seat with just your family and friends to watch Key West's Famous sunsets. View Dolphins, Turtles, and all kinds of Marine Life. Take the helm, l... More

When you book a private charter on the Daydreams Sailboat, your captain and first mate will help you plan the perfect experience for you and your guests! Your 90 minute Dolphin Sightseeing Sail on our Daydreams sailboat will inclu... More

Sail around Key West on a romantic, nighttime sailing experience aboard Schooner America 2.0! This 1.5-hour sail by moonlight is perfect for date night or an evening out with family and friends. Departing in the evening as the moo... More

Set sail on North America's largest day sailing Catamaran, The Caribbean Spirit, and Miami's premier sailing and swimming activity. We include water, soda and peanuts and pretzels to snack on while onboard, Our guests are welcome ... More

Your 90 minute Dolphin Sightseeing Sail on our Daydreams sailboat will include a scenic trip through Grand Lagoon and along the coast of Shell Island. Enjoy a relaxing sail in the Gulf of Mexico and look for dolphins along the way... More

Explore the picturesque Intracoastal Waterway and relax with adventure. Experience breathtaking coastal scenery or unwind while spotting local wildlife during serene nature sails. Perfect for couples, families, or anyone looking t... More

Meet at Miami Beach on Lincoln Road for a 7am departure and we will take a double decker bus and travel to the most famous Key, Key West. When we arrive at 10:30am you will have time to walk around and enjoy Key West. Make it over... More

This is the most hands-on sailing experience in Miami. As soon as you get in the boat you become part of the crew. Our goal is to perform as a unit and get the boat to sail as fast as possible. However, if you are looking for a mo... More

Sail into the vibrant Miami nightlife aboard a double-decker boat for the ultimate party experience. This 3-hour Miami booze cruise offers a unique nightclub atmosphere on the water, complete with a FREE open bar serving unlimited... More

We would welcome an opportunity to host you and your guest aboard our luxury sailing yachts. Our staff and captains are friendly and eager to assist in making your experience a wonder memory. This 2-hour sail gives passengers a ... More

Jump aboard Hannah Banana Boat Charters for the ultimate small-group water adventure! Gather your favorite people and set sail on our spacious 48' private yacht "La Vie Dansante" through Florida’s stunning Intracoastal Waterway.... More

Set sail on a private charter in Panama City, FL, where relaxation meets adventure. Captain Jon and his co-host Carrie create an intimate atmosphere perfect for couples, families, or friends seeking a memorable outing. Whether it'... More

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks,... More

The Snorkeling Safari is a must-do when visiting Destin. Pop open your favorite drinks and let your professional, USCG-licensed captain cruise you through the heart of Destin Harbor while you soak in the scenery and the good vibes... More

What makes this experience truly special is that it is a private charter designed entirely around your group. Unlike crowded tours with fixed schedules, this trip offers a relaxed and flexible experience where the day can be tailo... More