Top 10 Sailing in Key West

Destination: Key West.
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 the perfect blend of natural beauty, maritime history, and the thrill of the open sea. Don't forget your camera – this is a photo opportunity you won't want to miss! Book your spot now and get ready to create memories that will last a lifetime.
Known For: Key West Water Tours, Key West Half-day Tours, Key West Shore Excursions, Key West Small Group, Key West Ports of Call Tours, Key West Private and Luxury, Key West New Product, Key West Sailing.
Duration: Around 3 hours.

Destination: Key West.
This private charter is designed for a relaxed, flexible day on the water, perfect for groups who want a casual, unstructured experience. Instead of a formal, guided eco-tour, this trip offers a more laid-back vibe, allowing you to create your own adventure. Connect with Key West's abundant wildlife as you cruise the waters in search of our resident coastal dolphins. From there, we'll head to a secluded sandbar, a pristine shallow-water oasis where you can unwind and enjoy the tranquility. This tour is ideal for those who prefer to relax and socialize. Spend your time floating, swimming, or simply lounging with a cold beverage in hand. While snorkeling is an option, it is not a guided activity on this trip, making it perfect for guests who are more interested in a leisurely day on the water than a structured snorkel excursion. We'll provide a snack of fresh, organic fruit from Date & Thyme, and the trip is BYOB so you can bring your favorite drinks.
Known For: Key West Likely To Sell Out, Key West Snorkeling, Key West New Product, Key West Sailing, Key West On the Water, Key West Whale Watching, Key West Dolphin Watching, Key West Likely to Sell Out, Key West Swimming.
Duration: Around 4 hours.

Destination: Key West.
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 moon comes up over Key West, enjoy star gazing opportunities and a moonlit sky as the boat glides through the majestic waters at night.
Known For: Key West Water Tours, Key West Night Tours, Key West Night Cruises, Key West Private and Luxury, Key West Sailing, Key West Likely to Sell Out, Key West Likely To Sell Out.
Duration: Around 1 hour and a half.

Destination: Key West.
Get out to the Key West barrier coral reef in style on a former luxury sailing catamaran yacht now licensed for 30 passengers, but with only 17 passengers maximum. Avoid the crowds and enjoy sailing, coral reef snorkeling and the wild dolphins that live, feed and breed right along the south side of Key West. Get that yacht feeling with Champagne Service from your professional crew. Tickets are fully refundable if canceled outside of two weeks in advance!
Known For: Key West Sailing, Key West New Product, Key West On the Water, Key West Dolphin Watching, Key West Whale Watching, Key West Snorkeling.
Duration: Around 3 hours.

Destination: Key West.
Join us aboard Schooner America 2.0 in Key West for a fun night time experience. During this night cruise in Key West, guests can enjoy unobstructed views of the sweeping night sky and a fun adventure in Key West at night. Please note there are different options for this experience. Select departures will have live narration from a seasoned local astronomer, or a local guide sharing nautical superstitions with Key West's most famous ghost stores. Select options accordingly at check-out.
Known For: Key West Eco Tours, Key West Sailing, Key West Water Tours, Key West Night Tours, Key West Night Cruises, Key West Private and Luxury, Key West Likely to Sell Out, Key West Likely To Sell Out, Key West New Product.
Duration: Around 2 hours.

Destination: Key West.
Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. Enjoy a festive hot cocoa and holiday treats as we glide along with water for a fun night in Key West. Our beautiful 105-foot Schooner America 2.0 in full holiday decor that's sure to get you into the Christmas spirit in Key West harbor.
Known For: Key West Sailing, Key West Likely to Sell Out, Key West Music Tours, Key West Likely To Sell Out, Key West New Product, Key West Private and Luxury, Key West Adventure Tours, Key West Water Tours, Key West Christmas, Key West Art Tours.
Duration: Around 1 hour and a half.

Destination: Key West.
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 amazing natural wildlife with up to five others, before sailing back to shore at sunset.
Known For: Key West Private Sightseeing Tours, Key West Swimming, Key West Water Tours, Key West Sailing, Key West Half-day Tours, Key West Snorkeling, Key West Zombie, Key West On the Water, Key West Adventure Tours, Key West Zombie Slice, Key West Sunset Cruises.
Duration: Around 4 hours.

Destination: Key West.
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, learn how to raise and trim the sails, or just sit back and relax. Enjoy a private sunset cruise off the coast of Key West See the sites of Key West from the water Snacks and beverages included Fun for an entire group or family Private guides for a more personalized experience. Enjoy a private sunset sail off the coast of Key West and see the sights of Key West. Bring your favorite alcoholic beverages to enjoy while watching the sunset. Knowledgeable Captains to explain the art of sailing.
Known For: Key West Private and Luxury, Key West Private Sightseeing Tours, Key West Sunset Cruises, Key West New Product, Key West Water Tours, Key West Sailing, Key West Adventure Tours.
Duration: Around 2 hours.

Destination: Key West.
Sail with a smaller group of guests on our 65 foot schooner. Enjoy wines from around the world. Indulge in a variety of IPA, Import or domestic beers. Taste an assortment of appetizers. Enjoy a beautiful sunset while on the water. We provide 8 Varieties of Wine - 4 Red, 3 White & a Champagnoise • 5 Premium Beers - Imported & Domestic • Charcuterie Boards - Meats, cheeses, crackers, fruit, crudités, chocolate • Sodas and bottled water
Known For: Key West Sailing, Key West Spring Break, Key West Likely To Sell Out, Key West Likely to Sell Out, Key West On the Water, Key West Wine Tastings, Key West Excellent Quality.
Duration: Around 2 hours.

Destination: Key West.
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 comfortable. We limit passengers to just 36, guaranteeing you'll have room to move about and have an intimate evening experience. Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of captaining a traditional tall ship. With the painted sky as an exquisite backdrop, your sunset sail takes you past Key West’s Historic Seaport, Mallory Square’s Sunset Celebration, the Navy Mole where the big ships dock and the civil war era Fort Zachary Taylor. Soak in these sights while enjoying a glass of premium wine, an icy cold premium beer, full cocktail bar or soft drinks.
Known For: Key West New Product, Key West Excellent Quality, Key West Best Conversion, Key West Romantic Tours, Key West Sunset Cruises, Key West Sailing, Key West Top Product, Key West Water Tours, Key West Nature and Wildlife Tours, Key West Private and Luxury.
Duration: Around 2 hours.