Skip to content. Their schooners also offer a popular Wind & Wine sunset sail where guests sample fine wines from around the world while the sun sets. In 1513, Spanish explorer Ponce de Leon sailed the waters around Key West in search of the legendary Fountain of Youth. Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you. Our sailing trips provide the ideal way to check out the Keys, from the water! Definitely spacious. Explore Trips. Bay Side sailing conditions are characterized by 5 to 15 knot breezes and small seas that usually run a foot or less. Sail Away Key West is your source for the most luxurious private catamaran charters in Key West. From Key Largo to Key West many good anchorages can be found. Enjoy private day sailing charters in Key West, Florida. Complete with Sailing Lessons! TripAdvisor. The Florida Keys run approximately 120 from just north of Key Largo down to Key West. You can enjoy these Florida Keys activities here at Key Lime Sailing Club and Cottages in Key Largo. The staff were MORE than helpful and so fun to talk with. More time exploring, more islands, reefs, and shore excursions! Our daily sunset sails, sail/snorkel/kayak trips are limited to 25 guests, and our captains and staff go above and beyond to make sure your trip is the highlight of your Key West adventure. Bay and the fascinating coral … (813) 601-5243. WHAT TO BRING Bring your own alcohol, beer or wine if … We had an amazing vacation at the Key Lime Club and so much fun sailing in the Keys! Quite comfortable. Our 4+ night trips are actually more popular than the shorter trips! They won our 2020 Video Contest where they'll get a … 40 ratings. Laid back relaxed fun atmosphere. Calypso Sailing charters day, sunset and overnight sailing adventures in the Florida Keys. Sailing the Keys Whether you charter a boat and crew, or bare-boat your own cruise, the gin clear water of the Atlantic is your playground and expressway from island to island. Private & Shared Sailing Charters Sunset Sail Key West. We are owner operated and can accommodate a wide variety of sailing experiences from sunset cruises, family day sails, overnight excursions and beyond. Danger Charters sets sail where others can't, and without the huge crowds. Captained and Bareboat Keys Yachts Charters Available! 305-304-7999 The Bloody Pirate is a beautiful schooner sailing in the beautiful Florida Keys. All-Inclusive Private Sailing Charter Key West and Cape Cod. We sail where others don't. Let 30 years of experience on the reefs and waters around Key Largo set you free to discover. Explore our trusted fleet and 25 worldwide destinations. Get inspired with our most popular trips! Sunny Sail Charters - Marathon, Florida Keys, Florida - Monroe County - Come sail with us on the beautiful, clear waters of the Florida Keys. We offer full service sailing charters aboard our beautiful 45 foot sloop, Griffin. We provide sailing classes from basic sailing to advanced cruising and coastal navigation. Sailing, kayaking, paddle boarding, fishing, snorkeling, and more! Private Sunset Sail. Nearly 500 years later, Key West sailing charters follow in his wake, offering the same promise of exploration and youthful rejuvenation. 1-888-579-4782 5 Blocks from the Cruise Ship Docks • The Historic Seaport • Pier D • Downtown Key West, Florida. Sailing in the Florida Keys … Charters Read More » 3 Day / 2 Night Packages Sailing Vacations are so easy with us in the Florida Keys! Excite yourself with the starburst blaze of colors that is the Key West sunset on a luxurious sunset sail. A world leader in yacht charters and experts in bareboat and flotilla yacht sailing vacations. key west boat tours Free Spirit Sailing Charters Come and Enjoy an afternoon in the sun on board the Sailing Vessel Free Spirit! Learn More Or just sit back, … We are a boutique yacht charter company that specializes in Bareboat and Crewed Charter, ASA Sailing … BAREBOAT Charters Come enjoy our Islands in Paradise! 4.89/5. Check out the video made by our dear guests, the Carlson family. Interested in a longer trip? after 800+ ratings. We have a full schedule of sailing trips from January 2021 to the end of July 2021 in St Vincent & The Grenadines. From our marina you are minutes from sailing . She is named after the famous Code Rum cocktail drink. While enjoying one of our Florida sailing vacations, you can spend your time wind surfing off of Miami, snorkeling off the Florida Keys, or even fishing for marlin and other big game fish. Loved the relaxed atmosphere, the family feeling at the tiki, and being able to use the water toys was a big plus. Take one of our gorgeous sunset cruises, set sail for fun day on the water or let us help you plan a custom sailing vacation in The Keys. Calypso Sailing was established in 1988 with locations in both Key Largo and Key West that specialize in luxury sailing vacations on Leopard catamarans. Yacht Charters, Sales & Management - 1 (800) 327-0228 She is moored in Garrison Bight at the Key West Municipal Marina. Avg. Daysailing Trips and Rentals Daysailing Trips Daysailing Rentals Sunset Sailing Private Day Sailing Trips – USCG Captain Onboard – No Sailing Experience Needed –Reservations may be made 1 week prior to Sailing based on availability. PLEASE ASK ABOUT OUT 4-5-6 night SAILING TRIPS, OUR MOST POPULAR TRIP IS Key Largo TO Key West, IDEALLY DONE IN 5-6 nights. Additionally, a Florida sailing vacation or Florida Keys sailing vacation from Sailing Ship Adventures provides access to a wide range of water sports not commonly found on larger cruise lines. Answer 31 of 50: We'll be visiting Key West in October and have heard good things about some of the nude sailing charters that they have. View Sailing Charters Completely personal. Sail Charters. We look forward to planning your customized itinerary so that we can share with you our passion for sailing as well as the stunning waters, reefs, and wildlife of the Florida Keys. “MORNING STAR CHARTERS” Florida Keys, Key Largo Sailing-Snorkeling-Kayaking-Sunsets 2 to 6 individual passengers or single groups of up to 6. Enjoy an exciting Keys sailing adventure and watch us hoist her red sails on a true tall ship.. She can accommodate intimate private parties or large groups up to 38 people for day charters or 24 overnight. Check out our 4-7 night SAILING TRIPS on Viator, such as Key Largo TO Key West, IDEALLY DONE IN 5-6 nights. Experience the beauty and wonder of an unspoiled tropical paradise without ever leaving the Continental United States. 2 Hrs. For those with a yearning to experience more adventure, a trip to the Marquesas Islands or the Dry Tortugas and Fort Jefferson will give you some great offshore experience. Our 4+ night trips are actually more popular than the shorter trips! According to Paul Keever of Key Largo, Florida, there are islands out in the Everglades that are great destinations, as well as jungle tours that cruisers can make via kayak or—if their draft is shallow enough and their sense of adventure strong enough—sailboat. Dine aboard under the stars…or ashore at our island’s favorite Tiki Huts. Sail to the Marquesas Keys Anchor for three hours near the mangrove Take a guided tour aboard the 12 ft inflatable boat to see the abandoned Cuban “chug” boats Drive through the inside harbor on the return to the boat. Southernmost Sunset Sail with Full Bar and Hors d’Oeuvres. Enjoy the beauty of the Florida Keys. Enjoy our captained sailing/ snorkeling or sunset sails, both bayside and oceanside. Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas. We have many unforgettable sailing trips around the Caribbean for singles, solo travellers, couples, and small groups.. Our cabin charters range from day sails to 7 or 9-night adventure sails. Owner-operated. You can sail, snorkel & explore. Enjoy our Captained sailing/ snorkeling or sunset Sails, both Bayside & Oceanside. The Keys are easy to get to. Danger Charters: Snorkel and kayak Key West's mangrove islands and shallow backcountry on a full-day or half-day sail with Danger Charters. Let 30 … Other Key West Boat Tours & Adventures. Florida Keys Charters: A cruise through the Florida Keys is an attractive alternative to an extended cruise in the Bahama's. Learn to sail, immerse yourself in the live-aboard lifestyle, and explore Key West aboard a Rogue Angel, Kaimana, Southern Crosser, and more. At the end of a 110-mile-long chain of islands, stretched like a string of pearls across a Caribbean blue sea lies charmed Key West, it is here you will find Florida Yachts Charters. We offer day sailing, snorkeling, island hopping, and sunset cruise (upon request). Experience unforgettable sailing yacht charters in some of the world's greatest destinations. Laid back relaxed fun atmosphere. Cooler & Ice 1/2 Day – 4hours 9am-1 or 1-5 $330 + tax Full Day 9 … Daysailing Read More » Learn the fundamentals of sailing! Whether it is a sunset cruise or day sailing adventure, Catamaran ECHO is the best choice! Give our love to Captain G, Irene, James and CJ! Groups of … The best destinations are in our backyard. Breezin the Keys with Captain Dees - Private sailing charters, sailing lessons, snorkeling, weddings and memorials. Harness the wind with a sailing vacation aboard an innovative catamaran or sleek monohull in one of over 20 idyllic destinations. More time exploring, more islands, reefs, and shore excursions! 2 to 6 individual passengers or single groups up to 12. Explore the Florida Keys with Fun in the Sun Yachts - Florida Keys Sailing Charter. This location is minutes from the airport, and is a convenient 'jumping off point' for Sailing Charters to the Florida Keys or across the Gulf Stream to The Bimini Island Chain in the Bahamas. Key West Sailing Charters. 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