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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

6 Trips

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
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 ExperienceRacing & Performance

Grenada Sailing Week

Grenada • Caribbean
Next: 31 January - 5 February 2027
From
—
1 date available
Runs in Jan
Mile Builder
Any ExperienceTraining

To The South

Sint Maarten & Grenada • Caribbean
Next: 27 February - 6 March 2027
From
US$4,550
1 date available
Runs in Feb
Any ExperienceTraining

Eastern Caribbean Passage

Grenada & Sint Maarten • Caribbean
Next: 12 - 20 March 2027
From
US$4,850
1 date available
Runs in Mar
Mile Builder
Any ExperienceTraining

Caribbean Offshore Intensive

Sint Maarten & Grenada • Caribbean
Next: 27 March - 3 April 2027
From
US$4,850
1 date available
Runs in Mar

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

6 trips found

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
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 ExperienceRacing & Performance

Grenada Sailing Week

Grenada • Caribbean
Next: 31 January - 5 February 2027
From
—
1 date available
Runs in Jan
Mile Builder
Any ExperienceTraining

To The South

Sint Maarten & Grenada • Caribbean
Next: 27 February - 6 March 2027
From
US$4,550
1 date available
Runs in Feb
Any ExperienceTraining

Eastern Caribbean Passage

Grenada & Sint Maarten • Caribbean
Next: 12 - 20 March 2027
From
US$4,850
1 date available
Runs in Mar
Mile Builder
Any ExperienceTraining

Caribbean Offshore Intensive

Sint Maarten & Grenada • Caribbean
Next: 27 March - 3 April 2027
From
US$4,850
1 date available
Runs in Mar