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Extraordinary sailing adventures for everyone

Browse trips chosen by sailors for sailors - no signup needed

Vetted operators only
Secure booking
Trusted by 50,000+ sailors

44 Trips

Any ExperienceTraining

Croisière Formation FFV dans les Grenadines

Martinique • Caribbean
Next: 7 - 14 November 2026
From
—
15 dates available
Runs Nov - May
Intermediate & BeginnerTraining

RYA Day Skipper Practical

United Kingdom • Europe
Next: 11 - 15 November 2026
From
—
8 dates available
Runs Nov - Mar
BeginnerTraining

RYA Competent Crew

United Kingdom • Europe
Next: 11 - 15 November 2026
From
—
8 dates available
Runs Nov - Mar
Mile Builder
Any ExperienceTraining

Wind & Waves Seminar

U.S. Virgin Islands • Caribbean
Next: 3 - 7 December 2026
From
US$3,850
2 dates available
Runs in Dec
Mile Builder
Advanced & IntermediateExpedition

The Three Seas Expedition: Pula to Sardinia

Croatia & Italy • Europe
Next: 13 - 23 December 2026
From
—
1 date available
Runs in Dec
Beginner & IntermediateCruising

St Lucia Christmas Cruise

St. Lucia • Caribbean
Next: 19 - 26 December 2026
From
—20% off
1 date available
Runs in Dec
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Extraordinary sailing adventures for everyone

Browse trips chosen by sailors for sailors - no signup needed

Vetted operators only
Secure booking
Trusted by 50,000+ sailors

44 trips found

Any ExperienceTraining

Croisière Formation FFV dans les Grenadines

Martinique • Caribbean
Next: 7 - 14 November 2026
From
—
15 dates available
Runs Nov - May
Intermediate & BeginnerTraining

RYA Day Skipper Practical

United Kingdom • Europe
Next: 11 - 15 November 2026
From
—
8 dates available
Runs Nov - Mar
BeginnerTraining

RYA Competent Crew

United Kingdom • Europe
Next: 11 - 15 November 2026
From
—
8 dates available
Runs Nov - Mar
Mile Builder
Any ExperienceTraining

Wind & Waves Seminar

U.S. Virgin Islands • Caribbean
Next: 3 - 7 December 2026
From
US$3,850
2 dates available
Runs in Dec
Mile Builder
Advanced & IntermediateExpedition

The Three Seas Expedition: Pula to Sardinia

Croatia & Italy • Europe
Next: 13 - 23 December 2026
From
—
1 date available
Runs in Dec
Beginner & IntermediateCruising

St Lucia Christmas Cruise

St. Lucia • Caribbean
Next: 19 - 26 December 2026
From
—20% off
1 date available
Runs in Dec
Any ExperienceCruising

The Grenadines - Caribbean Christmas

Grenada & Martinique • Caribbean
Next: 20 December 2026 - 2 January 2027
From
—15% off
1 date available
Runs in Dec
Mile Builder
Intermediate & AdvancedExpedition

The Final Push Outwards: Sardinia to Gibraltar

Italy & Gibraltar • Europe
Next: 24 - 31 December 2026
From
—
1 date available
Runs in Dec
Mile Builder
Intermediate & AdvancedExpedition

The Atlantic Threshold: Gibraltar to the Canaries

Gibraltar & Spain • Europe
Next: 1 - 9 January 2027
From
—
1 date available
Runs in Jan
Mile Builder
AdvancedExpedition

Uphill to Brazil - 2200 NM Blue Water Passage

Martinique & Brazil • Caribbean
Next: 6 - 24 January 2027
From
—
1 date available
Runs in Jan
Atlantic
Any ExperienceRacing & Performance

RORC Transatlantic Race

Spain & Antigua & Barbuda • Europe
Next: 7 - 20 January 2027
From
—
1 date available
Runs in Jan
BeginnerTraining

Catamaran Bareboat certification

British Virgin Islands • Caribbean
Next: 10 - 17 January 2027
From
US$4,050US$4,50010% off
4 dates available
Runs Jan - May
Any ExperienceExpedition

Race and Explore the Southern Caribbean

Antigua & Barbuda • Caribbean
Next: 13 January - 8 February 2027
From
—
1 date available
Runs in Jan
Mile Builder
Any ExperienceTraining

Caribbean Offshore Challenge

U.S. Virgin Islands & Grenada • Caribbean
Next: 14 - 23 January 2027
From
US$5,250
1 date available
Runs in Jan
Any ExperienceExpedition

St. Vincent & Grenadines Expedition

St. Lucia • Caribbean
Next: 15 - 24 January 2027
From
—
1 date available
Runs in Jan
Any ExperienceRacing & Performance

Barbados Sailing Week

Barbados • Caribbean
Next: 16 - 22 January 2027
From
—
1 date available
Runs in Jan
Mile Builder
Any ExperienceTraining

Windward to Leeward Training

Sint Maarten • Caribbean
Next: 30 January - 6 February 2027
From
US$5,200
1 date available
Runs in Jan
Any ExperienceExpedition

Blast in San Blas Islands | Aruba → San Blas Islands → Colon

Panama • Americas
Next: 31 January - 8 February 2027
From
US$3,493US$4,99030% off
1 date available
Runs in Jan
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