Experience

Upcoming Cruises and Flotillas

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.

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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.

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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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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$1,250
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Islands of Belize, Central America A Guided Flotilla

Belize Sailing Vacations
Availability : Jun - 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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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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Offshore Passage, Bermuda to NYC A Learn-To-Sail Voyage

American Sailing
Availability : Jun 28, 2024
108 / 117 / 208 / 217

Embrace the adventure of a lifetime with our exclusive Learn to Sail vacation. Journey from Bermuda’s serene shores to the iconic Manhattan Marina, mastering the art of sailing and earning ASA credentials on the majestic Arabella. Don’t miss this unparalleled blend of education, adventure, and luxury at sea.

From$3,995$3,799
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Grand Tour of New England Aboard Arabella A LUXURY CRUISE

American Sailing
Availability : August 2024

From the moment you board Arabella in Newport, Rhode Island, the tone is set for a sailing adventure. Your week aboard Arabella will be filled with full sails on the way to Martha’s Vineyard, Nantucket, and Cuttyhunk. This is more than a sailing vacation; it’s an adventure for the soul.

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

Whitecaps Sailing School
Availability : Aug 31 - Sep 7   |   Sep 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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A REGATTA EXPERIENCE

Trieste, Italy – 2024 Barcolana 56Participate In A Unique Regatta Experience

American Sailing & North U
Availability : Oct 9, 2024

Join American Sailing and North U at Barcolana 56 in Trieste, Italy from October 9-13, 2024! Be part of the world’s largest sailing race, where camaraderie meets competition. Whether you’re a seasoned sailor or just love the sea, experience the inclusive spirit of Barcolana with us. Don’t miss this chance to sail amidst 2,600 boats and 16,000 sailors in a festival atmosphere like no other!

From$2,300
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EXPLORE MALLORCA ABOARD CHRONOS A LUXURY CRUISE

American Sailing
Availability : Oct 21, 2024

Embark on a 6-day luxury sailing adventure aboard Chronos Yacht, exploring Mallorca to Menorca with American Sailing. Enjoy personalized service, secluded coves, and stunning coastlines with a small, passionate group. This intimate voyage offers full-board luxury, breathtaking views, and unique experiences in the heart of the Balearic Islands. Set sail for an unforgettable journey this fall.

From$2,975
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The Bahamas, Caribbean A Guided Flotilla

Whitecaps Sailing School
Availability : Dec 7-14, 2024

Join Whitecaps Sailing School in the Bahamas for an extraordinary sailing adventure. Explore turquoise waters, encounter dolphins, reefs, and sea turtles, all guided by expert ASA instructors.

From$2,300
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A BVI ESCAPE ABOARD ARABELLA A LUXURY CRUISE

American Sailing
Availability : Dec 2024 | Jan 2025 | Feb 2025

Embark on a transformative journey through the British Virgin Islands aboard Arabella with American Sailing. From the lively shores of Jost Van Dyke to the serene beauty of Virgin Gorda, every moment is promised to be infused with laughter, camaraderie, and pure joy. Lose yourself in the rhythm of island life, where each day brings new adventures and lifelong friendships. Your dream itinerary awaits – let Arabella be your guide through paradise.

From$2,550
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PRICE INCREASES 7/1/24

British Virgin Islands, Caribbean A Guided Flotilla

Annapolis Sailing School
Availability : Jan 31-Feb 7 & Feb 8-Feb 15

Join our vibrant flotilla for an unforgettable voyage through the BVI’s azure waters. Enjoy daily sailing excursions, island hopping, and leisurely activities like snorkeling and beachcombing. Whether you’re a seasoned sailor or a novice, this trip promises endless fun and relaxation in paradise.

From$2,350
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PRICE INCREASES 7/1/24

British Virgin Islands, Caribbean A Learn-To-Sail Vacation

Annapolis Sailing School
Availability : Jan 31-Feb 7 & Feb 8-Feb 15, 2025
104 / 114

Embark on a sailing adventure through the picturesque BVI while earning your ASA 104 and 144 credentials. Our seasoned skippers will guide you through every aspect of sailing, from provisioning to navigation, ensuring a comprehensive learning experience amidst stunning island backdrops.

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