Sailing Guides
Destination overviews, course recommendations, seasonal planning, and honest comparisons to help you choose the right sailing experience.
Destination Guides
Everything you need to know about sailing in each destination.
Sailing in British Virgin Islands – Courses, Seasons & What to Expect
Everything you need to know about sailing in British Virgin Islands. Caribbean sailing paradise with perfect conditions ASA certification courses from $2950.
Sailing in Croatia – Courses, Seasons & What to Expect
Everything you need to know about sailing in Croatia. Mediterranean sailing with stunning coastline and islands ASA certification courses from $2750.
Sailing in Madeira – Courses, Seasons & What to Expect
Everything you need to know about sailing in Madeira. Atlantic island sailing with dramatic landscapes ASA certification courses from $2650.
Sailing in St. Martin – Courses, Seasons & What to Expect
Everything you need to know about sailing in St. Martin. Dual-nation Caribbean island with French and Dutch culture ASA certification courses from $2850.
Sailing in Tahiti – Courses, Seasons & What to Expect
Everything you need to know about sailing in Tahiti. Exotic Pacific sailing in French Polynesia ASA certification courses from $3450.
Best Courses by Audience
Find the right sailing course for your experience level, group, or occasion.
Best Learn to Sail Vacation for Honeymoon
Best honeymoon sailing vacation. Learn to sail together in paradise – private cabin, stunning destinations, ASA certification, and unforgettable memories.
Best Sailing Course for Advanced Sailors
Best advanced sailing courses. ASA 104, 105, 106, and 114 certifications for experienced sailors. Offshore, catamaran, and night sailing in challenging destinations.
Best Sailing Course for Beginners
The best sailing course for beginners. Learn to sail in 7 days with ASA certification. No experience needed – our expert instructors start from scratch in stunning destinations.
Best Sailing Course for Catamaran
Best catamaran sailing course. Earn your ASA 114 Cruising Catamaran certification. Learn multihull handling, docking, and passage-making aboard modern charter catamarans.
Best Sailing Course for Women
Best women-only sailing course. Learn to sail in a supportive, all-female environment. ASA certified, female instructors, stunning destinations. Build confidence on the water.
Best Sailing School for Corporate Teams
Best corporate sailing team-building experience. ASA certification courses that build leadership, communication, and teamwork. Custom packages for 8-40 people.
Best Sailing Trip for Solo Travelers
Best sailing trip for solo travelers. Join a crew of fellow adventurers, share a cabin to save money, and make lifelong friends while earning your ASA certification.
Best Sailing Vacation for Couples
Find the best sailing vacation for couples. Compare romantic destinations, shared cabin options, and certification courses perfect for partners learning together.
Best Sailing Vacation for Families
Best family sailing vacation – kids and parents learn together. ASA certification courses in safe, stunning destinations with expert instructors. Ages 12+.
Best Sailing Vacation for Groups
Best group sailing vacation. Book a whole boat for your friend group (6-8 people). ASA certification, island-hopping, and the ultimate shared adventure.
Best Sailing Vacation for Spring Break
Best spring break sailing vacation. Skip the resort – learn to sail, island-hop the Caribbean, and earn your ASA certification. The adventure spring break you actually want.
Seasonal Availability
Plan your certification around the best season and destination.
ASA 101 + 103 Christmas & New Year 2026-27
Book your ASA 101 + 103 course for Christmas & New Year 2026-27. Holiday sailing in the Caribbean. Christmas at anchor, New Year under the stars, and ASA certification to start the new year. Destinations: BVI, St. Martin, Bahamas.
ASA 101 + 103 Fall Sailing 2027
Book your ASA 101 + 103 course for Fall Sailing 2027. Shoulder season with great value. Late Mediterranean and early Caribbean sailing at lower prices. Destinations: Croatia, Greece, BVI, Thailand.
ASA 101 + 103 Memorial Day Weekend 2027
Book your ASA 101 + 103 course for Memorial Day Weekend 2027. Kick off summer with a sailing certification. Great conditions in the Caribbean and early Mediterranean season. Destinations: BVI, Croatia, Greece, St. Martin.
ASA 101 + 103 Spring Break 2027
Book your ASA 101 + 103 course for Spring Break 2027. Spring break is prime time for Caribbean sailing. Perfect trade winds, warm water, and peak season conditions. Destinations: BVI, Bahamas, St. Martin, USVI.
ASA 101 + 103 Summer 2027
Book your ASA 101 + 103 course for Summer 2027. Mediterranean sailing season. Long days, warm waters, and ideal wind conditions across Europe. Destinations: Croatia, Greece, France-Brittany, Madeira.
ASA 101 + 103 Thanksgiving Week 2027
Book your ASA 101 + 103 course for Thanksgiving Week 2027. Thanksgiving sailing in the Caribbean. Skip the turkey, gather your crew, and give thanks on the water. Destinations: BVI, Bahamas, St. Martin.
ASA 101 + 103 Winter Escape 2026-27
Book your ASA 101 + 103 course for Winter Escape 2026-27. Caribbean and tropical winter sailing. Escape the cold with warm-water courses in the BVI, Bahamas, Thailand, and beyond. Destinations: BVI, Bahamas, Thailand, St. Martin, St. Lucia.
ASA 101 Christmas & New Year 2026-27
Book your ASA 101 course for Christmas & New Year 2026-27. Holiday sailing in the Caribbean. Christmas at anchor, New Year under the stars, and ASA certification to start the new year. Destinations: BVI, St. Martin, Bahamas.
ASA 101 Fall Sailing 2027
Book your ASA 101 course for Fall Sailing 2027. Shoulder season with great value. Late Mediterranean and early Caribbean sailing at lower prices. Destinations: Croatia, Greece, BVI, Thailand.
ASA 101 Memorial Day Weekend 2027
Book your ASA 101 course for Memorial Day Weekend 2027. Kick off summer with a sailing certification. Great conditions in the Caribbean and early Mediterranean season. Destinations: BVI, Croatia, Greece, St. Martin.
ASA 101 Spring Break 2027
Book your ASA 101 course for Spring Break 2027. Spring break is prime time for Caribbean sailing. Perfect trade winds, warm water, and peak season conditions. Destinations: BVI, Bahamas, St. Martin, USVI.
ASA 101 Summer 2027
Book your ASA 101 course for Summer 2027. Mediterranean sailing season. Long days, warm waters, and ideal wind conditions across Europe. Destinations: Croatia, Greece, France-Brittany, Madeira.
ASA 101 Thanksgiving Week 2027
Book your ASA 101 course for Thanksgiving Week 2027. Thanksgiving sailing in the Caribbean. Skip the turkey, gather your crew, and give thanks on the water. Destinations: BVI, Bahamas, St. Martin.
ASA 101 Winter Escape 2026-27
Book your ASA 101 course for Winter Escape 2026-27. Caribbean and tropical winter sailing. Escape the cold with warm-water courses in the BVI, Bahamas, Thailand, and beyond. Destinations: BVI, Bahamas, Thailand, St. Martin, St. Lucia.
ASA 103 Christmas & New Year 2026-27
Book your ASA 103 course for Christmas & New Year 2026-27. Holiday sailing in the Caribbean. Christmas at anchor, New Year under the stars, and ASA certification to start the new year. Destinations: BVI, St. Martin, Bahamas.
ASA 103 Fall Sailing 2027
Book your ASA 103 course for Fall Sailing 2027. Shoulder season with great value. Late Mediterranean and early Caribbean sailing at lower prices. Destinations: Croatia, Greece, BVI, Thailand.
ASA 103 Memorial Day Weekend 2027
Book your ASA 103 course for Memorial Day Weekend 2027. Kick off summer with a sailing certification. Great conditions in the Caribbean and early Mediterranean season. Destinations: BVI, Croatia, Greece, St. Martin.
ASA 103 Spring Break 2027
Book your ASA 103 course for Spring Break 2027. Spring break is prime time for Caribbean sailing. Perfect trade winds, warm water, and peak season conditions. Destinations: BVI, Bahamas, St. Martin, USVI.
ASA 103 Summer 2027
Book your ASA 103 course for Summer 2027. Mediterranean sailing season. Long days, warm waters, and ideal wind conditions across Europe. Destinations: Croatia, Greece, France-Brittany, Madeira.
ASA 103 Thanksgiving Week 2027
Book your ASA 103 course for Thanksgiving Week 2027. Thanksgiving sailing in the Caribbean. Skip the turkey, gather your crew, and give thanks on the water. Destinations: BVI, Bahamas, St. Martin.
ASA 103 Winter Escape 2026-27
Book your ASA 103 course for Winter Escape 2026-27. Caribbean and tropical winter sailing. Escape the cold with warm-water courses in the BVI, Bahamas, Thailand, and beyond. Destinations: BVI, Bahamas, Thailand, St. Martin, St. Lucia.
ASA 104 + 114 Christmas & New Year 2026-27
Book your ASA 104 + 114 course for Christmas & New Year 2026-27. Holiday sailing in the Caribbean. Christmas at anchor, New Year under the stars, and ASA certification to start the new year. Destinations: BVI, St. Martin, Bahamas.
ASA 104 + 114 Fall Sailing 2027
Book your ASA 104 + 114 course for Fall Sailing 2027. Shoulder season with great value. Late Mediterranean and early Caribbean sailing at lower prices. Destinations: Croatia, Greece, BVI, Thailand.
ASA 104 + 114 Memorial Day Weekend 2027
Book your ASA 104 + 114 course for Memorial Day Weekend 2027. Kick off summer with a sailing certification. Great conditions in the Caribbean and early Mediterranean season. Destinations: BVI, Croatia, Greece, St. Martin.
ASA 104 + 114 Spring Break 2027
Book your ASA 104 + 114 course for Spring Break 2027. Spring break is prime time for Caribbean sailing. Perfect trade winds, warm water, and peak season conditions. Destinations: BVI, Bahamas, St. Martin, USVI.
ASA 104 + 114 Summer 2027
Book your ASA 104 + 114 course for Summer 2027. Mediterranean sailing season. Long days, warm waters, and ideal wind conditions across Europe. Destinations: Croatia, Greece, France-Brittany, Madeira.
ASA 104 + 114 Thanksgiving Week 2027
Book your ASA 104 + 114 course for Thanksgiving Week 2027. Thanksgiving sailing in the Caribbean. Skip the turkey, gather your crew, and give thanks on the water. Destinations: BVI, Bahamas, St. Martin.
ASA 104 + 114 Winter Escape 2026-27
Book your ASA 104 + 114 course for Winter Escape 2026-27. Caribbean and tropical winter sailing. Escape the cold with warm-water courses in the BVI, Bahamas, Thailand, and beyond. Destinations: BVI, Bahamas, Thailand, St. Martin, St. Lucia.
ASA 104 Christmas & New Year 2026-27
Book your ASA 104 course for Christmas & New Year 2026-27. Holiday sailing in the Caribbean. Christmas at anchor, New Year under the stars, and ASA certification to start the new year. Destinations: BVI, St. Martin, Bahamas.
ASA 104 Fall Sailing 2027
Book your ASA 104 course for Fall Sailing 2027. Shoulder season with great value. Late Mediterranean and early Caribbean sailing at lower prices. Destinations: Croatia, Greece, BVI, Thailand.
ASA 104 Memorial Day Weekend 2027
Book your ASA 104 course for Memorial Day Weekend 2027. Kick off summer with a sailing certification. Great conditions in the Caribbean and early Mediterranean season. Destinations: BVI, Croatia, Greece, St. Martin.
ASA 104 Spring Break 2027
Book your ASA 104 course for Spring Break 2027. Spring break is prime time for Caribbean sailing. Perfect trade winds, warm water, and peak season conditions. Destinations: BVI, Bahamas, St. Martin, USVI.
ASA 104 Summer 2027
Book your ASA 104 course for Summer 2027. Mediterranean sailing season. Long days, warm waters, and ideal wind conditions across Europe. Destinations: Croatia, Greece, France-Brittany, Madeira.
ASA 104 Thanksgiving Week 2027
Book your ASA 104 course for Thanksgiving Week 2027. Thanksgiving sailing in the Caribbean. Skip the turkey, gather your crew, and give thanks on the water. Destinations: BVI, Bahamas, St. Martin.
ASA 104 Winter Escape 2026-27
Book your ASA 104 course for Winter Escape 2026-27. Caribbean and tropical winter sailing. Escape the cold with warm-water courses in the BVI, Bahamas, Thailand, and beyond. Destinations: BVI, Bahamas, Thailand, St. Martin, St. Lucia.
ASA 105 + 106 Christmas & New Year 2026-27
Book your ASA 105 + 106 course for Christmas & New Year 2026-27. Holiday sailing in the Caribbean. Christmas at anchor, New Year under the stars, and ASA certification to start the new year. Destinations: BVI, St. Martin, Bahamas.
ASA 105 + 106 Fall Sailing 2027
Book your ASA 105 + 106 course for Fall Sailing 2027. Shoulder season with great value. Late Mediterranean and early Caribbean sailing at lower prices. Destinations: Croatia, Greece, BVI, Thailand.
ASA 105 + 106 Memorial Day Weekend 2027
Book your ASA 105 + 106 course for Memorial Day Weekend 2027. Kick off summer with a sailing certification. Great conditions in the Caribbean and early Mediterranean season. Destinations: BVI, Croatia, Greece, St. Martin.
ASA 105 + 106 Spring Break 2027
Book your ASA 105 + 106 course for Spring Break 2027. Spring break is prime time for Caribbean sailing. Perfect trade winds, warm water, and peak season conditions. Destinations: BVI, Bahamas, St. Martin, USVI.
ASA 105 + 106 Summer 2027
Book your ASA 105 + 106 course for Summer 2027. Mediterranean sailing season. Long days, warm waters, and ideal wind conditions across Europe. Destinations: Croatia, Greece, France-Brittany, Madeira.
ASA 105 + 106 Thanksgiving Week 2027
Book your ASA 105 + 106 course for Thanksgiving Week 2027. Thanksgiving sailing in the Caribbean. Skip the turkey, gather your crew, and give thanks on the water. Destinations: BVI, Bahamas, St. Martin.
ASA 105 + 106 Winter Escape 2026-27
Book your ASA 105 + 106 course for Winter Escape 2026-27. Caribbean and tropical winter sailing. Escape the cold with warm-water courses in the BVI, Bahamas, Thailand, and beyond. Destinations: BVI, Bahamas, Thailand, St. Martin, St. Lucia.
ASA 114 Christmas & New Year 2026-27
Book your ASA 114 course for Christmas & New Year 2026-27. Holiday sailing in the Caribbean. Christmas at anchor, New Year under the stars, and ASA certification to start the new year. Destinations: BVI, St. Martin, Bahamas.
ASA 114 Fall Sailing 2027
Book your ASA 114 course for Fall Sailing 2027. Shoulder season with great value. Late Mediterranean and early Caribbean sailing at lower prices. Destinations: Croatia, Greece, BVI, Thailand.
ASA 114 Memorial Day Weekend 2027
Book your ASA 114 course for Memorial Day Weekend 2027. Kick off summer with a sailing certification. Great conditions in the Caribbean and early Mediterranean season. Destinations: BVI, Croatia, Greece, St. Martin.
ASA 114 Spring Break 2027
Book your ASA 114 course for Spring Break 2027. Spring break is prime time for Caribbean sailing. Perfect trade winds, warm water, and peak season conditions. Destinations: BVI, Bahamas, St. Martin, USVI.
ASA 114 Summer 2027
Book your ASA 114 course for Summer 2027. Mediterranean sailing season. Long days, warm waters, and ideal wind conditions across Europe. Destinations: Croatia, Greece, France-Brittany, Madeira.
ASA 114 Thanksgiving Week 2027
Book your ASA 114 course for Thanksgiving Week 2027. Thanksgiving sailing in the Caribbean. Skip the turkey, gather your crew, and give thanks on the water. Destinations: BVI, Bahamas, St. Martin.
ASA 114 Winter Escape 2026-27
Book your ASA 114 course for Winter Escape 2026-27. Caribbean and tropical winter sailing. Escape the cold with warm-water courses in the BVI, Bahamas, Thailand, and beyond. Destinations: BVI, Bahamas, Thailand, St. Martin, St. Lucia.
Girls Only ASA 101 Christmas & New Year 2026-27
Book your Girls Only ASA 101 course for Christmas & New Year 2026-27. Holiday sailing in the Caribbean. Christmas at anchor, New Year under the stars, and ASA certification to start the new year. Destinations: BVI, St. Martin, Bahamas.
Girls Only ASA 101 Fall Sailing 2027
Book your Girls Only ASA 101 course for Fall Sailing 2027. Shoulder season with great value. Late Mediterranean and early Caribbean sailing at lower prices. Destinations: Croatia, Greece, BVI, Thailand.
Girls Only ASA 101 Memorial Day Weekend 2027
Book your Girls Only ASA 101 course for Memorial Day Weekend 2027. Kick off summer with a sailing certification. Great conditions in the Caribbean and early Mediterranean season. Destinations: BVI, Croatia, Greece, St. Martin.
Girls Only ASA 101 Spring Break 2027
Book your Girls Only ASA 101 course for Spring Break 2027. Spring break is prime time for Caribbean sailing. Perfect trade winds, warm water, and peak season conditions. Destinations: BVI, Bahamas, St. Martin, USVI.
Girls Only ASA 101 Summer 2027
Book your Girls Only ASA 101 course for Summer 2027. Mediterranean sailing season. Long days, warm waters, and ideal wind conditions across Europe. Destinations: Croatia, Greece, France-Brittany, Madeira.
Girls Only ASA 101 Thanksgiving Week 2027
Book your Girls Only ASA 101 course for Thanksgiving Week 2027. Thanksgiving sailing in the Caribbean. Skip the turkey, gather your crew, and give thanks on the water. Destinations: BVI, Bahamas, St. Martin.
Girls Only ASA 101 Winter Escape 2026-27
Book your Girls Only ASA 101 course for Winter Escape 2026-27. Caribbean and tropical winter sailing. Escape the cold with warm-water courses in the BVI, Bahamas, Thailand, and beyond. Destinations: BVI, Bahamas, Thailand, St. Martin, St. Lucia.
RYA Day Skipper Christmas & New Year 2026-27
Book your RYA Day Skipper course for Christmas & New Year 2026-27. Holiday sailing in the Caribbean. Christmas at anchor, New Year under the stars, and ASA certification to start the new year. Destinations: BVI, St. Martin, Bahamas.
RYA Day Skipper Fall Sailing 2027
Book your RYA Day Skipper course for Fall Sailing 2027. Shoulder season with great value. Late Mediterranean and early Caribbean sailing at lower prices. Destinations: Croatia, Greece, BVI, Thailand.
RYA Day Skipper Memorial Day Weekend 2027
Book your RYA Day Skipper course for Memorial Day Weekend 2027. Kick off summer with a sailing certification. Great conditions in the Caribbean and early Mediterranean season. Destinations: BVI, Croatia, Greece, St. Martin.
RYA Day Skipper Spring Break 2027
Book your RYA Day Skipper course for Spring Break 2027. Spring break is prime time for Caribbean sailing. Perfect trade winds, warm water, and peak season conditions. Destinations: BVI, Bahamas, St. Martin, USVI.
RYA Day Skipper Summer 2027
Book your RYA Day Skipper course for Summer 2027. Mediterranean sailing season. Long days, warm waters, and ideal wind conditions across Europe. Destinations: Croatia, Greece, France-Brittany, Madeira.
RYA Day Skipper Thanksgiving Week 2027
Book your RYA Day Skipper course for Thanksgiving Week 2027. Thanksgiving sailing in the Caribbean. Skip the turkey, gather your crew, and give thanks on the water. Destinations: BVI, Bahamas, St. Martin.
RYA Day Skipper Winter Escape 2026-27
Book your RYA Day Skipper course for Winter Escape 2026-27. Caribbean and tropical winter sailing. Escape the cold with warm-water courses in the BVI, Bahamas, Thailand, and beyond. Destinations: BVI, Bahamas, Thailand, St. Martin, St. Lucia.
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