Experience

LEARN TO SAIL VACATIONS

American Sailing schools can be found in destinations around the world and many of them offer learn-to-sail vacation packages. Combine your next trip to a popular destination with an amazing sailing education experience.

Spring Mile Builder to Chios A Learn-To-Sail Vacation

Athens Sailing Academy
Availability : May 02 - 09, 2026
104 / 105 / 106 / 114 / IPC

Spring Mile Builder is an intensive, live-aboard sailing experience designed to fast-track your skills through real offshore miles. Sail day and night in the Aegean, rotate through active crew roles, build confidence on longer passages, and log qualifying miles toward ASA certifications—all while exploring the Greek Islands under expert instruction.

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Corfu & North Ionian Sea Learn-to-Sail Vacation with Fair Winds Sailing

Corfu & The North Ionian Sea, Greece A Learn-To-Sail Vacation

Fair Winds Sailing Greece
Availability : Various Dates May - October, 2026
101 / 102 / 103 / 104 / 105 / 106 / 114 / 116 / 118

Sail through the stunning waters of Corfu and the North Ionian Sea with Fair Winds Sailing Greece. This all-inclusive adventure blends hands-on instruction with island hopping, swimming in crystal bays, and exploring charming coastal villages. Learn from Captain Dimitris Bampakos, a seasoned Greek Navy officer and master ASA instructor, as you earn certifications and experience the magic of Greece. Where every day brings new horizons and memories.

From$1,990
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Islands of Belize, Central America A Learn-To-Sail Vacation

Belize Sailing Vacations
Availability : Various Dates May - Dec 2026
Various Dates May - Dec 2026

Belize’s sailing experience extends beyond the sea, offering captivating inland ventures. With BSV’s fully crewed catamarans, guests enjoy the ultimate all-inclusive charter, accessing the world’s largest living barrier reef and remote sites.

From$2,795
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Central Ionian Sea, Greece A Learn-To-Sail Vacation

Fair Winds Sailing Greece
Availability : Various Dates May - October, 2026
103 / 104 / 114 / 118

Embark on an unforgettable Catamaran Learn to Sail Vacation with Fair Winds Sailing Greece, an American Sailing affiliate. Departing from Lefkas Marina, this adventure takes you through the Central Ionian Sea, a breathtaking region celebrated for its turquoise waters, gentle “maistro” winds, and lush green islands steeped in history and charm.

From$2,490
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North Adriatic Islands Learn-To-Sail Vacation

Islands of North Adriatic A Learn-To-Sail Vacation

Annapolis Sailing School
Availability : May 16 & Jun 20, 2026
101 / 103 / 104

Experience the beauty of the Adriatic Sea as you sail along Croatia’s breathtaking coastline, famous for its turquoise waters, charming islands, and vibrant seaside towns. Discover hidden coves, ancient ports, and picturesque villages while learning to sail with experienced local instructors. This program combines hands-on training with leisure, allowing you to relax, explore, and gain valuable sailing experience aboard a comfortable monohull or catamaran. From Rijeka to Rab, every stop offers a perfect blend of culture, nature, and adventure.

From$2,100
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Corfu LTSV Fair Winds Sailing

Corfu & Paxos Islands, Greece A Learn-To-Sail Vacation

Fair Winds Sailing Greece
Availability : Various Dates May - September, 2026
101 / 102 / 103 / 104 / 105 / 106 / 114 / 116 / 118

Sail the beautiful waters of Corfu and Paxos Islands with Fair Winds Sailing Greece. Departing from historic Mandraki Port, this all-inclusive Learn-to-Sail adventure blends hands-on training with island hopping, swimming in turquoise bays, and exploring charming harbors, all led by Captain Dimitris Bampakos, a seasoned Greek Navy officer and ASA Senior Master Instructor.

From$1,990
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Whitecaps Volos Kickoff - Sail Greece

Whitecaps Volos Kickoff – Sail Greece A Learn-To-Sail Vacation

Whitecaps Sailing School
Availability : Jun 06 - 13 & Jun 27 - Jul 04, 2026
101 / 103 / 104

Set sail with Whitecaps Sailing in Volos, Greece, and earn your ASA 101–104 certifications while exploring the tranquil Sporades Islands. This hands-on sailing adventure blends expert instruction with the beauty and culture of coastal Greece. Perfect for beginners or sailors advancing their skills.

From$2,295
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Lake Michigan, Wisconsin A Learn-To-Sail Vacation

Sea Safaris Sailing School
Availability : Jun 08 - 12, 2026
101 /103 / 104

Learn to sail on Lake Michigan with a hands-on vacation departing from Milwaukee. Sail aboard a modern Jeanneau 409 while building real-world skills like sail trim, helming, docking, navigation, and safety procedures. Cruise Wisconsin’s scenic shoreline with stops in Port Washington and Sheboygan. Designed for beginners and motivated novices, this immersive experience blends expert instruction with the adventure of true big-water sailing.

From$2,257
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women's only bvi vacation

Women’s-Only Week in the British Virgin Islands A Learn-To-Sail Vacation

Horizon Sailing School
Availability : Jun 13-20, 2026
101 / 103 / 104

Join Horizon Sailing School for a women-only learn-to-sail vacation in the beautiful British Virgin Islands. During this week-long liveaboard experience, you’ll build confidence on the water while sailing between iconic islands like Norman Island, Virgin Gorda, and Jost Van Dyke. Aboard a comfortable 34–44 ft monohull, you’ll learn sailing fundamentals, coastal cruising, and bareboat skills while earning ASA 101, 103, and 104 certifications. With small groups, expert instruction, and time to snorkel, explore beaches, and enjoy island life, this trip combines sailing education with a relaxed Caribbean adventure.

From$3,495
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San Juan Islands A Learn-To-Sail Vacation

San Juan Sailing
Availability : Jun 20 - 26 & Jul 18 - 24, 2026
101 / 102 / 103 / 104 / 111

Spend a week living aboard and learning to sail in the beautiful San Juan Islands. Practice sailing, navigation, docking, mooring, and anchoring while navigating currents, tidal swings, and island winds. Each evening you’ll anchor or dock in a new bay or island port. By the end of the week, you’ll earn ASA 101 through ASA 104 certifications. Accommodations, instruction, fuel, and most meals are included for an unforgettable sailing adventure.

From$3,120
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6 Days in Barbados A Learn-To-Sail Vacation

Wet & Salty Adventure Sailing School
Availability : Jun 28-Jul 03 & Nov 01-06, 2026
103 / 104

Join Wet & Salty Adventure Sailing School in Barbados for a 6-day intensive liveaboard course combining ASA 103 (Coastal Cruising) and ASA 104 (Bareboat Cruising) to help sailors refine their skills and gain confidence as a skipper. With steady trade winds, deep blue waters, and hands-on training in navigation, anchoring, and passage planning, this Caribbean adventure prepares you for independent cruising and chartering worldwide.

From$3,050
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Poros, Greece

Poros, Greece A Learn-To-Sail Vacation

Athens Sailing Academy
Availability : Jul 01 - 30, 2026
101 / 103 / 104 / 105 / 106

As Europe’s oldest ASA-certified sailing school, Athens Sailing Academy offers world-class instruction in Greece’s stunning waters. Train in Poros during summer, where sunshine, warm seas, and steady winds create the perfect learning conditions, or at our Athens headquarters year round. Our experienced English-speaking instructors share their passion for sailing and deep local knowledge to help you master the art of confident, safe cruising through the Greek islands.

From$1,850
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Costa Dorada, Spain A Learn-To-Sail Vacation

Red Sky Sailing Barcelona
Availability : Jul 04-10, Jul 11-17, Aug 29-Sep 04, & Sep 05-11, 2026
101 / 103 / 104

Sail the Costa Dorada on a 7-day coastal passage from Barcelona, exploring historic ports, clear-water coves, and vibrant seaside towns. This hands-on itinerary combines real-world sailing with ASA 101, 103, and 104 training, building skills progressively each day. With calm Mediterranean conditions, scenic anchorages, and unforgettable evenings ashore, it’s the ideal blend of certification, adventure, and culture.

From$3,500
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Barcelona, Spain A Learn-To-Sail Vacation

Red Sky Sailing Barcelona
Availability : Jul 18-24, Jul 25-31, Aug 01-07, & Aug 15-21, 2026
101 / 103 / 104

Barcelona Sailing Week offers a one week learn to sail experience where students earn ASA 101, 103, and 104 certifications while sailing the Mediterranean by day and enjoying the energy of Barcelona each night. Based out of Port Olímpic, the program combines consistent sailing conditions, hands on instruction, and a coastal passage to Sitges with the flexibility to stay aboard or in a hotel, creating a balanced experience of skill building, adventure, and city life.

From$3,500
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9 Days in Barbados A Learn-To-Sail Vacation

Wet & Salty Adventure Sailing School
Availability : Aug 16-24 & Nov 29-Dec 07, 2026
101 / 103 / 104

Embark on the ultimate sailing adventure with our comprehensive 9-day ASA Liveaboard Monohull Class. This immersive course is designed for aspiring sailors seeking to master the essentials of sailing, with hands-on training and real-world experience. Over the span of a week, you will cover ASA 101, 103, and 104 certifications, ensuring you are well-prepared to handle various sailing conditions and navigate with confidence!

From$3,350
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Costa Brava, Spain A Learn-To-Sail Vacation

Red Sky Sailing Barcelona
Availability : Sep 05-11, Sep 19-25, Sep 26-Oct 02, & Oct 17-23, 2026
101 / 103 / 104

Sail the Costa Brava from Barcelona and experience real Mediterranean conditions, dramatic cliffs, and historic coastal towns. This hands-on itinerary combines ASA 101, 103, and 104 training with open-water passages and variable winds, building true confidence and skill. By the end of the week, students earn three certifications and are ready to charter anywhere in the Mediterranean.

From$3,500
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Womens Only Poros Greece learn to sail vacation

Women-Only Classes in Poros, Greece A Learn-To-Sail Vacation

Athens Sailing Academy
Availability : Sep 12 - 19, & Sep 26 - Oct 03, 2026
101 / 103 / 104 / 105 / 106

Discover Women of the Wind, an all-female ASA sailing experience in Greece where women learn, grow, and take the helm with confidence. Sail through the Greek islands, build real seamanship skills, earn certification, and join a supportive community of passionate women sailors.

From$1,900
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Lefkas, Ithaca, & Kefalonia, Greece A Catamaran Learn-To-Sail Vacation

Fair Winds Sailing Greece
Availability : Various Dates September - October, 2026
103 / 104 / 114 / 118

Sail through Greece’s breathtaking Ionian Sea, where calm maistro winds, turquoise waters, and lush islands set the stage for an unforgettable adventure. Explore the captivating beauty of Lefkas, Ithaca, and Kefalonia, discovering historic towns, hidden coves, and seaside tavernas that make these legendary islands some of the world’s most cherished sailing destinations.

From$2,490
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Monohull BVI

British Virgin Islands A Monohull Learn-To-Sail Vacation

Horizon Sailing School
Availability : Nov 07-14, 2026
101 / 103 / 104

Learn to sail while exploring the beautiful British Virgin Islands on this week-long liveaboard adventure with Horizon Sailing School. Aboard a comfortable 34–44 ft monohull, you’ll build sailing skills while visiting iconic destinations like Norman Island, Virgin Gorda, and Jost Van Dyke. During the trip you can earn ASA 101, 103, and 104 certifications, gaining the knowledge and confidence needed to bareboat a monohull. With small groups, expert instruction, and time to snorkel, explore beaches, and enjoy island life, this experience blends hands-on sailing training with a relaxing Caribbean vacation.

From$3,495
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British virgin islands

British Virgin Islands A Learn-To-Sail Vacation

Learn To Sail San Diego
Availability : Nov 13 - 21, 2026
103 / 104 / 114

Join the Ultimate Sailing Experience! Set sail with us in the stunning British Virgin Islands, whether you want your own boat or prefer to share with others. Certified ASA instructors can be on board, guiding you through ASA 103, 104, and 114 certifications as you explore one of the world’s best sailing destinations. Don’t need certifications? Charter captains are available by request.

From$3,500
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Catamaran BVI Vacation

British Virgin Islands A Catamaran Learn-To-Sail Vacation

Horizon Sailing School
Availability : Nov 14-21, 2026
103 / 104 / 114

Learn to sail while exploring the beautiful British Virgin Islands aboard a 40–44 ft catamaran. During this week-long liveaboard adventure with Horizon Sailing School, you’ll gain hands-on sailing experience while visiting iconic islands like Norman Island, Virgin Gorda, and Jost Van Dyke. The course includes ASA 103, 104, and 114 certifications, onboard accommodations, instruction, and most meals.

From$3,995
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