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Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843119-43WX1KYR7DCRX9RTYZD2/WN3%2Bb2dkR5u7xtK%25TDx0Cw.jpg Adventure Gallery - Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843176-G7MBK8JTOX7JYIESQS5O/cyx61bg5TnegxKkN5Vfs1A.jpg Adventure Gallery - Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843143-21HT4297KSIZSJECXXJ4/hQWyjv5%2BSxu6IR%2BQ%2BHJIYw.jpg Adventure Gallery - Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843151-YL2PEX0UHUHO3FSNE27Q/BeFswHQvQZ674iXq%25Mx2%2Bg.jpg Adventure Gallery - Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843185-YLT6PE1BGTGX3TABE7TD/rXQtrGRsS961znx4%2B7Cy1Q.jpg Adventure Gallery - Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843130-6PV5LFVZNGTRKYC7Y8LO/czh%254EBQSfSFOjyaMr%2BIIQ.jpg Adventure Gallery - Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843110-W4NUO43JVAFKYSV336Q1/%2BkIF6n2DTBmRRDlfOdOy6w.jpg Adventure Gallery - Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843092-NVZ7YOFOOY0837DA6A6Y/gEXyKyM1TNy4Fjm15eqfHA.jpg Adventure Gallery - Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843085-EPVTH5MRZW8X58FPJ20D/vV5hOtjRRsG6RFo4JNGe4g.jpg Adventure Gallery - Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843066-DVDU8LVPE1QL2YD9EREH/olM%25zwh%25RvaxdTgmXS6V8w.jpg Adventure Gallery - Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843167-NU8LQGBVXHDKTVH8KIWL/%2B%25yZL1otR0inwdLSBbexEw.jpg Adventure Gallery - Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843073-1GG9N0M1ZS5X6J8GXA28/jiqfIOIcRm6OHNZsD%2BiqMw.jpg Adventure Gallery - Key West Charters https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645843058-8DUI0Y01GPG79DJRNKBK/TWh6gob%25RviX8lKcS7QdIg.jpg Adventure Gallery - Key West Charters https://seagypsy.us/adventures daily 0.75 2024-02-01 https://seagypsy.us/adventures/sunset-sailing-charter monthly 0.5 2023-09-24 https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645928806-4QX1BWCES2ENN2IA3NLU/IMG_2412.jpg Sailing Adventures - Sunset Sailing Charter - Private Sunset Sailing Charter 3 hours to experience the famous Florida sunset. Enjoy a glass of champagne, wine, or beer and the most romantic views of either Miami’s Biscayne Bay or the Key West coastline. Book this intimate private sailing experience for your group of up to 4 passengers. Contact us to schedule your sunset cruise! We will help you plan for bringing your favorite provisions or ordering a custom catering package. https://seagypsy.us/adventures/private-half-day-sailing-charter-zfls4-3lapf monthly 0.5 2023-10-02 https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1695485357958-GPZHQMS80G457JDRLV07/7B9594B0-C727-482B-A47F-B9E3494D3043.jpeg Sailing Adventures - Private Half-Day Sailing Charter - Private Half-Day Sailing Charter from Miami Fun in the sun! Enjoy your private sailboat charter for an entire morning or afternoon. Set the sails, cruise to the infamous Stiltsville in Biscayne Bay, or simply soak up the sun on the deck of your sailboat. Your Captain is USCG Masters-licensed and a US Sailing-certified Instructor and ready to help with loads of suggestions. Your classic sailboat is equipped with a fully equipped galley (kitchen), with cooler and ice. Add one of our optional Beverage and Provisions Packages for carefree hours on the water. A perfect half-day sailing adventure for your group of up to 6 passengers, including children. https://seagypsy.us/adventures/full-day-private-sailing-charter-9ax4z-gb846 monthly 0.5 2021-06-21 https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645928757-ULGSYAYMQRFSIVX1B90G/Lucia+40-2.jpg Sailing Adventures - Private Full-Day Sailing Charter - Private Full-Day Sailing Charter from Key West There’s no better way to experience the Florida Keys than from the water! When visiting Key West, charter a roomy sailing catamaran with Captain for an entire day. Set the sails, snorkel at a nearby reef, or simply soak up the sun on the wide deck of your comfortable sailing catamaran. Your Captain is USCG Masters-licensed and a US Sailing-certified Instructor and ready to help with loads of suggestions. Your charter catamaran has a fully equipped galley (kitchen), with refrigerator, cooler and ice. Add a Beverage and Provisions Package for a carefree day on the water. This is the perfect sailing catamaran adventure for your group of up to 6 passengers, including children. https://seagypsy.us/adventures/private-celebrations-rm9lf-xswdm monthly 0.5 2021-03-18 https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645928782-IRF90WE99UPV7CHL39C0/IMG_2433.jpg Sailing Adventures - Private Celebrations - Private Celebrations Celebrate any special occasion aboard our beautiful classic sailboats! To ensure safety and be ready to help with loads of suggestions, your experienced Captain will be USCG Masters-licensed and a US Sailing-certified Instructor. Our sailboats have a galley (kitchen), with cooler, and ice. Add an optional Beverage and Provisions Package for a carefree day or evening on the water. You'll have free use of the entire boat with generous deck spaces as well as the weather-protected salon. We will work with you on catering and decorations to make your celebration memorable. Private Celebrations are currently boarding in Key West and Miami. Simply request your departure date, then answer a few questions to let us help you build your private charter experience! https://seagypsy.us/adventures/classic-sailboat-photoshoots monthly 0.5 2023-09-23 https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/9aaa2055-3c6d-471b-898f-5dba147df720/7D0536F4-7C24-47CE-84D3-B1D30F5DD596.jpeg Sailing Adventures - Classic Sailboat Photoshoots - Miami Skyline Shoots Whether by day or night - a photoshoot with the Miami skyline as backdrop created lasting memories. https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1695483413315-BD8AKE7DZ099WZD8Z44G/image-asset.jpeg Sailing Adventures - Classic Sailboat Photoshoots - Classic Sailboat Photo & Video Shoots Book a classic sailboat as the perfect location for your next photo or video shoot! Our sailboats have been used in numerous private and commercial photoshoots, so we know what it takes to get the best shots. Boarding and departure location will be Miami or Key West. Click here to see impressions from past photoshoots and here for pictures of our classic sailboat. https://seagypsy.us/adventures/private-sailing-events monthly 0.5 2023-09-23 https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645928636-64BG0XIIMJ1SGR8CVJBM/RJZLfyRqRt6q2HXeQogeDA.jpg Sailing Adventures - Private Sailing Events - Private Sailing Events Experience a private luxury event aboard the most romantic classical sailboat! Plan your intimate event for up to 4 passengers or enjoy the magic of our professional event planners. Enjoy your private sailing adventure to go where you wish, whether it is the twinkling Miami skyline or the open water of Biscayne Bay. Stay comfortable on the boat with room for food and ice-cold drinks, running water, bathroom, and plenty of room to lounge. You are in the good hands of your qualified Captain and optional service crew. Private Celebrations are currently boarding in Miami. Simply request your departure date, then answer a few questions to let us help you build your private sailing event! https://seagypsy.us/adventures/custom-private-charter-a4x9d-f54jj monthly 0.5 2023-09-24 https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645928702-3WVB6963XEDFCZBZP9SB/IMG_2400.jpg Sailing Adventures - Custom Charter Package - Private Custom Charter Experience Is there anything involving sailing the ocean from Miami to the Florida Keys that we didn't cover? Please let us know, and we will help you create your adventure. https://seagypsy.us/adventures/private-sailing-instructions-hhfwb-r89k2 monthly 0.5 2021-10-14 https://seagypsy.us/adventures/custom-multi-day-sailing-charter-vacation-p6emt-s7l9j monthly 0.5 2023-09-24 https://images.squarespace-cdn.com/content/v1/640e1a4998e06141e89f7b98/1678645928757-ULGSYAYMQRFSIVX1B90G/Lucia+40-2.jpg Sailing Adventures - Sailing Charter Vacation - Crewed Sailing Charter - The Ultimate Bespoke Ocean Vacation Our fully crewed yacht charters are designed for those seeking an exclusive, exceptional, and truly remarkable vacation of a lifetime. Step aboard our premium, fully crewed private yachts. Our expert team is on hand to guide you through every planning step so your vacation goes smoothly from the start. Contact our experienced team, who can make your dream vacation a reality. How about a custom sailing catamaran vacation with family or friends? Our vessels are fully-equipped with everything needed for a live-aboard cruising catamaran and will accommodate your group of up to 6 passengers, including children. Board in Key West and enjoy your charter adventure to go where you wish in the Florida Keys. Immerse yourself in your destination and enjoy a different view every day. Relax on a spacious deck with a cocktail, while our professional crew takes care of every detail for you and your guests. Visit the beaches at Bahia Honda State Park or sail west to the Dry Tortugas and beautiful Loggerhead Key - we will help you design your custom itinerary. Snorkel the famous reefs of John Pennecamp Coral Reef, go on a paddle board tour, or just simply relax; the choices are yours! Your Captain is an experienced USCG Masters-licensed and US Sailing-certified instructor, who knows the best spots to island-hop up and down the Keys from Key West to Key Biscayne near Miami. Use the fully-stocked galley to prepare memorable meals and grill your fresh catch under the moon and stars. Charters are available as self-provisioned or full-service with a mate aboard who will work with you on your food and beverage choices, shop for, and prepare your meals. No clean-up required! Then experience comfortable and quiet nights at anchor under the stars in your three air-conditioned double cabins with private en-suite bathrooms.