Florida Keys Sailboat Charters
Alphabetical Listings ~ 41 ~
FROM WEST TO EAST (Key West to Key Largo)
KEY WEST SAILBOAT CHARTERS ~ 22 < Click for Key West Sailboat Charters
LITTLE TORCH KEY SAILBOAT CHARTERS ~ 1 ~
23 Miles from Key West
Coastal Sailing Adventures, Inc. - Little Torch Key, Florida Keys, Florida - Monroe County - Welcome aboard the Schooner Dream Catcher, designed and built for a spectacular sailing experience in the Florida Keys. We offer 2 to 6 hour private-charter sails accommodating up to 49 guests. At over 70 feet, this beautiful vessel features spacious sundecks, shaded decks, restrooms, complete galley, sleeping accommodations for 19 guests and much more.
MARATHON SAILBOAT CHARTERS ~ 5 ~
55 Miles from Key West
American Sailing Adventures - Marathon, Florida Keys, Florida - Monroe County - We are Licensed and Insured and Coast Guard Inspected and offer ASA Certified sailing lessons. We also offer half day and full day sailing charters in the Florida Keys. Come sail with us on the beautiful, crystal waters of the Florida Keys. Take one of our fantastic half day or set sail for a full day on the water in in The Keys. Our Florida Keys charters are fully crewed and private for up to 6 passengers.
Caribbean Soul Charters - Marathon, Florida - Relax at a Florida Keys weekly vacation rental that includes a sailboat with your stay. Our Florida Keys waterfront accommodation with a sailboat is an ideal place to stay for the experienced sailor. We offer a clean, comfortable, affordable vacation rental in the middle Florida Keys, 10 miles north of Marathon on Conch Key. Our room rentals include a 23 foot Com-Pac sailboat for your use and enjoyment.
Florida Keys Sailing - Marathon, Florida Keys, Florida - Monroe County - At Florida Keys Sailing our specialty is private live aboard sailing classes and sailing vacations with just you, your spouse, your family or friends. “Learn to Sail” or take an Advanced Course to further develop your sailing and navigation skills. Sailing instruction is offered here all year long on demand in our tropical setting. America’s Caribbean is the Florida Keys, with the only living coral reef in the continental USA.
Sailing Catamaran Sirius - Marathon, Florida - Monroe County - The Sailing Catamaran Sirius is a Coast Guard inspected 36ft by 24ft sailing catamaran with a 24 passenger capacity. Catamaran sailing offers a safe, stable, and comfortable setting for sailing with larger groups. Our business profile is green to the environment. Captain Dale Kamerzel has provided approximately 4,400 documented sailing charters performed in 10 years and a lifetime of sailing the waters of south Florida.
Sunny Sail Charters - Marathon, Florida Keys, Florida - Monroe County - Come sail with us on the beautiful, clear waters of the Florida Keys. 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. Our Florida Keys charters are fully crewed and private - with the exception of our our Just-For-Fun-Sail package, your party will have the whole boat to themselves.
ISLAMORADA SAILBOAT CHARTERS ~ 1 ~
81 Miles from Key West
Islander Watersports - Islamorada, Florida Keys, Florida - Monroe County - Enjoy breathtaking sunsets aboard the "Horizon Cat" Islamorada's only Sailing Catamaran. No need to travel 2 more hours to Key West to see our famous Sunsets here in the heart of the Florida Keys. Our 40 foot 24 passenger Sailing Catamaran awaits your arrival. Enjoy the beautiful warm evening weather and calm ride as the sun meets the sea. Bring your camera and a loved one, you won't want to miss this memorable sailing trip.
KEY LARGO SAILBOAT CHARTERS ~ 11 ~
98 Miles from Key West
Adventures Adrift - Key Largo, Florida Keys, Florida - Monroe County - High Seas Adventure aboard the Ketch Viewfinder! Custom charters for the day / half day / weekend getaways. We specialize in liveaboard adventures from overnights to multi day voyages through the Florida Keys. Enjoy cruising in comfort, snorkeling, diving & fishing aboard your own skippered private yacht. USCG Licensed and fully insured since 1997.
Calypso Watersports & Charters - Key Largo, Florida Keys, Florida - Monroe County - Calypso Watersports & Charters was created by Captain Lance Holmquist and has been sailing out of Key Largo since 1988. We specialize in extended charters but also offer day and sunset charters. Enjoy a luxury sailing vacation on one of our Leopard catamarans. Captained and bareboat charters are available on our 42ft and 47ft Leopard catamarans.
Key Largo Sailboat Charters - Key Largo, Florida Keys, Florida - Monroe County - Key Largo Sail School and Charter offers both crewed sailboat charters and sailing lessons in the first city on the Keys. Our ocean side dock locations in Garden Cove, Key Largo and Key West are set amongst the cream of the dive boats in what has been called “America’s premier dive capital.” Your sailboat charter or sailing lessons will take on the clear, blue, warm waters of the Atlantic Ocean. We are also a few mere minutes sail from America’s best live coral reefs.
Key Lime Sailing Club - Key Largo, Florida Keys, Florida - Monroe County - At the American Sailing Academy, located at the Key Lime Sailing Club and Vacation Cottages, you will learn from experienced professionals who provide the most comprehensive, safety first training available. If you're an experienced sailor, we invite you to use one of our own 22' sailboats with your cottage rental at no additional charge.
Morning Star Sailing Charters LLC - Key Largo, Florida Keys, Florida - Monroe County - Sailing, snorkeling on our 50' sailing yacht. Morning Star offers charters for two to six persons. We offer the opportunity for you to enjoy the beautiful waters of Key Largo in a fun and relaxed atmosphere. We are the longest existing sail, snorkel charter in the Florida Keys. In an area where businesses come and go, Captain Rick Winters has been successfully operating Morning Star Charters for the past 27 years.
Quicksilver Catamarans - Key Largo, Florida Keys, Florida - Monroe County - Your Vacation in Key Largo is not Complete Without a snorkeling and sailing adventure on our catamarans. Sail the calm, clear waters of Key Largo in the Florida Keys on the Reef Roamer and Quicksilver 50 ft catamarans. We offer private sunset charters for wedding ceremonies, corporate events, fundraisers, birthday parties, spreading of ashes etc. Our two vessels can accommodate 2 to 89 passengers.
Reef Runner Sailing - Key Largo, Florida Keys, Florida - Monroe County - Reef Runner Sailing offers a variety of sailing experiences in our locations in Panama City, Florida, and Key Largo. We also have affiliates in key locations of the Bahamas, the Caribbean, and the Greek Isles. Reef Runner Sailing School is an American Sailing Association (ASA) accredited sailing school. We offer a variety of Key Largo sailboat charters from a relaxing day sail with family or friends, a romantic sunset cruise, or a unique corporate team building sailing charter.
Rosa Del Mar Sailing - Key Largo, Florida Keys, Florida - Monroe County - Rosa Del Mar Sailing specializes in private sailing and snorkeling charters and vacations in Key Largo and the Florida Keys for up to 6 persons. On the Rosa Del Mar, each is trip is a private charter, with a maximum capacity of 6 persons, so there's no stumbling over bodies and gear to get off the boat. Spend an entire day or just a half-day sailing off Key Largo and snorkeling the azure waters of Molasses Reef and other locations in Pennekamp State Park.
Sunshine Coast Adventures - Key Largo, Florida Keys, Florida - Monroe County - Sunshine Coast Adventures is a Key Largo, Florida Keys sailing school specializing in ASA adventure sailing programs for youth, women, couples and anyone seeking a sailing vacation. We are an award winning ASA sailing school offering live aboard ASA sailing classes and sailing charters in the beautiful Florida Keys and the Bahamas. During a typical sailing vacation, we mix in some snorkeling, some sailing, some fishing, some kayaking and some relaxing.
Zephyrus Sailing Charters - Key Largo, Florida Keys, Florida - Monroe County - The sailboat Zephyrus is available for custom charters, special events, weddings, photo shoots, etc. for 1-6 guests. State Rooms available for our guests include 3 cabins with queen beds. Each cabin has its own private shower and head (restroom), deck shower, air-conditioning, TV/DVD/CD, Playstation 3, stereo sound system, iPOD compatible. Sailboat amenities include 2 person hammock, dine-in seating for 6, Bimini top, BBQ grill, 12 ft skiff with 25 HP outboard motor, boarding ladder and more.
MIAMI TO FLORIDA KEYS SAILBOAT CHARTERS ~ 3 ~
Bikini Sailing - Miami, Florida to Florida Keys - Sail from the beautiful city of Miami and the lovely warm waters of Biscayne Bay to the crystal clear waters of the Florida Keys. We offer private sailing instruction for couples, families and women's groups. Bikini Sailing was formed to promote the sport of sailing and cruising, and especially to encourage the increasing numbers of interested women to understand and enjoy the sport.
Juliet Sailing & Diving - Miami, Florida to Florida Keys - Offers customized week-long liveaboard diving itineraries on board a majestic 104’ schooner. Join us April through November as we sail and dive the crystal clear, turquoise waters of the Bahamas and the wreck-strewn waters of the Florida Keys, each winter explore the beauty and romance of Puerto Rico, and the US and British Virgin Islands
Florida Keys Catamaran Charters - Miami, Florida to Florida Keys - We offer fully crewed sailing and power catamaran charters for the pristine waters of the Florida Keys. We are based at Key Biscayne near Miami at the Crandon Park Marina and provide private sailboat charters from Miami to all destinations in the Florida Keys. The Alymaya is a 44 foot Lagoon catamaran. She is a sailing catamaran but also is powered by twin diesels, in case that there is not enough wind to sail during your charter. We sail year round in the Florida Keys.