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.

Islands of Belize, Central America A Learn-To-Sail Vacation

Belize Sailing Vacations
Availability : Dec 2025 - Dec 2026
101 / 103 / 104 / 105 / 106 / 114

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
0
View Details
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 : May 04-09, May 11-16, Jun 01-06, & Jun 22-27, 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
0
View Details
Corfu LTSV Fair Winds Sailing

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

Fair Winds Sailing Greece
Availability : May 18-23, May 25-30, Jun 08-13, & Jun 15-20, 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
0
View Details
lefkas ithica keflonia greece vacation

Lefkas, Ithaca, & Kefalonia A Catamaran Learn-To-Sail Vacation

Fair Winds Sailing Greece
Availability : Sep 19 - 26 & Sep 26 - Oct 03, 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, Kefalonia, Corfu, and Paxos, 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
0
View Details
Ionian Sea

Central Ionian Sea A Catamaran Learn-To-Sail Vacation

Fair Winds Sailing Greece
Availability : May 16 - 23 & 23 - 30, 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
0
View Details
Annapolis Sailing School BVI Flotilla

British Virgin Islands A Learn-To-Sail Vacation

Annapolis Sailing School
Availability : Feb 07 - 14 & 15 - 21, 2026
104 / 114

Join Annapolis Sailing School for an unforgettable Learn-to-Sail Vacation in the British Virgin Islands from February 7–14 or February 15–21, 2026. Sail aboard a 45’+ catamaran or 48’ monohull while exploring Tortola, Virgin Gorda, Anegada, Jost Van Dyke, and more, with opportunities to earn ASA 104 Bareboat Cruising and ASA 114 Cruising Catamaran certifications. Enjoy hands-on training, stunning anchorages, and the perfect balance of learning, adventure, and Caribbean relaxation.

From$2,500
0
View Details
Whitecaps Volos Kickoff - Sail Greece

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

Annapolis 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
0
View Details
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
0
View Details
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
0
View Details
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
0
View Details

San Juan Islands A Learn-To-Sail Vacation

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

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$3,120
0
View Details

Diesel Maintenance & Sailing in Denver, CO A Learn-To-Sail Vacation

Victoria Sailing School
Availability : Jan/Feb 2026
Marine Diesel

Join a unique three-day sailing vacation in Denver, Colorado, that combines hands-on marine diesel engine training with outdoor adventure. Enjoy expert instruction, meals, included tools, and an evening sail on scenic Chatfield Reservoir.

From$900
0
View Details