Experience

Upcoming Cruises and Flotillas

Islands of Belize, Central America A Guided Flotilla

Belize Sailing Vacations
Availability : Jan / Apr / May / Jun / Jul / Nov / Dec 2024

Explore Belize’s paradise islands on your own private luxury catamaran. Learn sailing from ASA certified instructors & crew. Snorkel, kayak, and fish in crystal clear waters. Enjoy gourmet meals & exotic drinks prepared by your crew. Experience a different destination every day on this ultimate sailing vacation!

From$2,995
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Society Islands in Tahiti, French Polynesia A Guided Flotilla

South Coast Sailing Adventures
Availability : February 17-March 2, 2024

Join our French Polynesia Flotilla and visit paradise on earth. Those who fly into the islands and stay at hotels experience only a part of the magic of these islands. It is only in sailing between the blue ocean and turquoise lagoons in the shadow of the majestic volcanic peaks.

From$6,500
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British Virgin Islands, Caribbean A Guided Flotilla

Sea Safaris Sailing School
Availability : February 24-March 2, 2024

Embark on an unforgettable adventure in the Caribbean BVIs with Sea Safari aboard a luxurious sailing catamaran. Discover the beauty of the British Virgin Islands while enjoying the spaciousness, speed, stability, and shallow draft that catamarans offer. This course is designed for both novice and experienced sailors who seek to explore the captivating waters of the Caribbean in style and comfort.

From$1,950
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Paraty in Brazil, South America A Guided Flotilla

Whitecaps Sailing School
Availability : April 6-13, 2024

Brazil is one of the most popular destinations on many tourists’ bucket list, but still widely unknown for its sailing culture. Join us as we set sail on an amazing flotilla from Paraty.

From$2,095
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Explore Croatia aboard Cataleya A Luxury Cruise

American Sailing
Availability : May 2024 / Sep 2024

Welcome aboard Cataleya a 30 meter luxury sailing yacht which will be your home for 8 days as you explore the Dalmation coast of Croatia. This trip will include stops in Split, Hvar, Korcula as well as a few anchorages that are the secrets of the captain and the crew. Join us on a once-in-a-lifetime sailing vacation.

From$2,800
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Italy’s Amalfi Coast, Mediterranean A Guided Flotilla

Whitecaps Sailing School
Availability : May 25-June 1, 2024

Sail the beautiful waters of the Amalfi Coast on this flotilla led by an experienced captain. You will have the opportunity to explore the amazing coastline of Italy and enjoy the local cuisine and culture.

From$2,095
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Greece & The Aegean Sea, Mediterranean A Guided Flotilla

Athens Sailing School
Availability : May 25-June 1, 2024

Athens Sailing Academy and American Sailing invite you to join us as we sail the beautiful Blue Aegean Sea. Depart from our base on Poros Island, just off Athens and discover ancient Castles and quaint anchorages and villages. You can choose from our large selection of Jeanneau Yachts, ranging from 34ft to 55ft.

From$1,400
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Croatia, The Dalmatian Islands A Guided Flotilla

Delta Sailing School
Availability : May 25-June 22, 2024

Set sail amidst the mesmerizing Dalmatian Islands of Croatia with Delta Sailing School! An ASA-accredited school, Delta Sailing School’s flotilla adventures cater to both novices and seasoned sailors alike, offering the opportunity to enhance your sailing skills and knowledge.

From$2,100
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Greece, Mediterranean A Guided Flotilla

Fair Winds Sailing
Availability : June 8-15, 2024

Join American Sailing and Fairwinds Sailing Greece on a journey from Corfu through the Corfu Islands. Our local captains from Fairwinds Sailing will take us to their favorite anchorages and introduce us to Greece as seen through their eyes. Corfu Island is in the north Ionian Sea, between Italy and Greece (Greek “Ιόνιο Πέλαγος” – Italian “Mare Ionio”). Corfu is considered one of the finest and most cosmopolitan islands in the Mediterranean. 

From$1,875
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Greece & The Ionian Sea, Mediterranean A Guided Flotilla

Whitecaps Sailing School
Availability : June 8-15, 2024

Sail in the “wake” of Ulysses in the Ionian Islands of Greece. We will leave from Lefkada and visit stunning places like Ithaca, Fiscardo, Meganisi, Kefalonia, Atakos and more. Swim in the crystalline clear waters of the Ionian Sea, and, as with all our flotillas, make new sailing friends!

From$2,095
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Lenny Shabes Sailing Festival ~ BVIs A Guided Flotilla

American Sailing
Availability : June 16-22, 2024

Join us for a week of sailing in paradise, as our late founder Lenny Shabes, set out to teach aspiring sailors to do. To pay tribute to all Lenny has done for the world of sailing, we are calling all sailors to partake in a week of festivities ranging from sundowners to regattas in the beautiful BVI’s.

From$2,250
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Victoria & the Gulf Islands, Pacific Northwest A Guided Flotilla

San Juan Sailing
Availability : June 22-28, 2024

Join fellow sailors for a week cruising the beautiful San Juan and Canadian Gulf Islands to Victoria, BC. The San Juan and adjacent Gulf islands are a cruising paradise boasting sheltered waters, magnificent marine parks, quiet villages, and welcoming marinas. Wildlife abounds on the land and in the sea, with deer, bald eagles, sea otters, and orca whales commonplace.

From$900
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Arabella Grand Tour of New England A Luxury Cruise

American Sailing
Availability : August 2024

Arabella is one of the most beautiful sailing yachts in the world. She epitomizes classic elegance and graceful style and has been an icon along the East Coast in summer and in the Caribbean in winter. Arabella is also US Coast Guard certified, one of the few mega yachts with this designation in our country.

From$2,200
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Dalmatian Islands of Croatia, Mediterranean A Guided Flotilla

Whitecaps Sailing School
Availability : September 7-14, 2024

Join our most popular itinerary in Croatia with visits to islands like Hvar, Brac, and Vis. This itinerary, which we started in 2009, has constantly remained the most popular choice for first-time sailors in Croatia.

From$2,150
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