Your 2 hour sunset charter on our 47-foot sailboat Daydreams 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. Wit... More

This is a luxury Sailboat Excursion for up to 6 guests. Our 47 ft Daydreams Sailboat has a great bow for sunbathing, aft seating area for enjoyment and a luxury salon, galley, cabins and marine head for your use. Get ready for fu... More

Discover Miami from a whole new perspective aboard one of the top-rated private boat experiences in the city, rated 4.9⭐ with 1.2k+ reviews on Google. Perfect for birthdays, bachelor or bachelorette parties, proposals, annivers... More

Join Sunset Watersports, Key West's Original Watersports Company for a day at Smathers Beach. We are the only company offering the Key West Beach Pass.... More

Whether you are a seasoned sailor or if this is your first time sailing, this will be a memorable visit!!! ;) *Children under age 5-not permitted to sail. *Not Suitable for Guests with mobility issues. *Participants must weigh l... More

Live the high life on this private chartered day sail in Key West. Set sail on your boat for a 90-minute adventure around the Florida Keys and view the city from the water in peace and tranquility. You may even get to see some fri... More

Join us on Sebago's newest trip, designed to allow guests to experience the waters around Key West as so many locals do, visiting little known, breathtakingly beautiful spots with small groups of friends while enjoying great food ... More

Upon agreeing to embark on this adventure with us, you'll formalize the arrangement through a straightforward bareboat charter. Now, let's talk logistics. The captain's compensation is a separate matter, settled directly at the ... More

Perfect for kids to grandparents, and perfect for couples! Always fun, relaxing, and uncrowded. Chill out in comfy seats, with beautiful views of the bay and National Seashore. Or explore the Condor: walk around, do the Titanic po... More

Embark on an unforgettable journey starting in Fort Lauderdale on the iconic New River, often called the “Venice of America.” This scenic waterway offers a beautiful blend of natural mangroves, luxurious waterfront homes, and ... 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

Embark on an unforgettable adventure to Key West, whether you’re a seasoned snorkeler or trying it out for the first time! This day trip from Fort Lauderdale promises thrilling experiences and breathtaking sights both above and ... More

Experience the magic of a Key West sunset from the water on this elegant 2-hour sailing cruise departing from the historic Key West Seaport. As the sails are raised and the breeze carries you across the sparkling Gulf waters, unwi... More

Sail around in style aboard a catamaran with a fun local avid sailor that wants to share his passion with you. Let Captain Kip take you to some of the best spots the area has to offer while you are visiting the Emerald Coast.... More

Historic Schooner. Champagne Sunset Toast. Elegant and Exclusive. Step aboard the historic schooner When And If, commissioned by General George Patton in the late 1930s, and sail into a breathtaking Key West sunset. Raise a champ... More

Fury’s Nights of Lights cruises offer a one-of-a-kind way to experience St. Augustine’s holiday magic from the water, giving guests sweeping, unobstructed views of the illuminated bayfront, the Bridge of Lions, and Castillo de... More

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

Sail aboard the fastest and most elegant schooner in Key West, Schooner America 2.0! This boat is a replica of the 1851 Schooner America that won the first America's Cup Race in 1851. Admire her beauty on the clear, calm Caribbean... 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

Experience sailing Key West on a majestic 2-masted schooner, just like adventurers from the 19th century, while enjoying the luxurious state-of-the-art accommodations of a modern passenger schooner. Her decks are spacious and comf... More