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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
31 Trips
Caribbean
Sailing Type
Experience Level
Dates
Any Experience
Training
Croisière Formation FFV dans les Grenadines
Martinique • Caribbean
Next: 7 - 14 November 2026
From
—
15 dates available
Runs Nov - May
Mile Builder
Any Experience
Training
Sailing the Tropical Trail
Bermuda & U.S. Virgin Islands • Caribbean
Next: 13 - 23 November 2026
From
US$7,550
1 date available
Runs in Nov
Mile Builder
Any Experience
Training
Wind & Waves Seminar
U.S. Virgin Islands • Caribbean
Next: 3 - 7 December 2026
From
US$3,850
2 dates available
Runs in Dec
Beginner & Intermediate
Cruising
St Lucia Christmas Cruise
St. Lucia • Caribbean
Next: 19 - 26 December 2026
From
—
20% off
1 date available
Runs in Dec
Any Experience
Cruising
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
Advanced
Expedition
Uphill to Brazil - 2200 NM Blue Water Passage
Martinique & Brazil • Caribbean
Next: 6 - 24 January 2027
From
—
1 date available
Runs in Jan
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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
31 trips found
List
Map
Caribbean
Sailing Type
Experience Level
Dates
Any Experience
Training
Croisière Formation FFV dans les Grenadines
Martinique • Caribbean
Next: 7 - 14 November 2026
From
—
15 dates available
Runs Nov - May
Mile Builder
Any Experience
Training
Sailing the Tropical Trail
Bermuda & U.S. Virgin Islands • Caribbean
Next: 13 - 23 November 2026
From
US$7,550
1 date available
Runs in Nov
Mile Builder
Any Experience
Training
Wind & Waves Seminar
U.S. Virgin Islands • Caribbean
Next: 3 - 7 December 2026
From
US$3,850
2 dates available
Runs in Dec
Beginner & Intermediate
Cruising
St Lucia Christmas Cruise
St. Lucia • Caribbean
Next: 19 - 26 December 2026
From
—
20% off
1 date available
Runs in Dec
Any Experience
Cruising
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
Advanced
Expedition
Uphill to Brazil - 2200 NM Blue Water Passage
Martinique & Brazil • Caribbean
Next: 6 - 24 January 2027
From
—
1 date available
Runs in Jan
Any Experience
Expedition
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 Experience
Training
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 Experience
Expedition
St. Vincent & Grenadines Expedition
St. Lucia • Caribbean
Next: 15 - 24 January 2027
From
—
1 date available
Runs in Jan
Any Experience
Racing & Performance
Barbados Sailing Week
Barbados • Caribbean
Next: 16 - 22 January 2027
From
—
1 date available
Runs in Jan
Mile Builder
Any Experience
Training
Windward to Leeward Training
Sint Maarten • Caribbean
Next: 30 January - 6 February 2027
From
US$5,200
1 date available
Runs in Jan
Any Experience
Cruising
Windward – Leeward Cruise
St. Lucia & Antigua & Barbuda • Caribbean
Next: 31 January - 7 February 2027
From
—
1 date available
Runs in Jan
Any Experience
Racing & Performance
Grenada Sailing Week
Grenada • Caribbean
Next: 31 January - 5 February 2027
From
—
1 date available
Runs in Jan
RORC
Intermediate & Advanced
Racing & Performance
RORC Caribbean 600
Antigua & Barbuda • Caribbean
Next: 16 - 23 February 2027
From
—
1 date available
Runs in Feb
RORC
Intermediate & Advanced
Racing & Performance
RORC Caribbean 600
Antigua & Barbuda • Caribbean
Next: 17 - 26 February 2027
From
—
1 date available
Runs in Feb
RORC
Any Experience
Racing & Performance
RORC Caribbean 600
Antigua & Barbuda • Caribbean
Next: 19 - 26 February 2027
From
—
1 date available
Runs in Feb
Mile Builder
Any Experience
Training
To The South
Sint Maarten & Grenada • Caribbean
Next: 27 February - 6 March 2027
From
US$4,550
1 date available
Runs in Feb
Mile Builder
Any Experience
Racing & Performance
Antigua - St. Maarten Mile Builder
Antigua & Barbuda & Sint Maarten • Caribbean
Next: 27 - 28 February 2027
From
—
1 date available
Runs in Feb
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