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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 40,000+ sailors
4 Trips
vi
Sailing Type
Experience Level
Dates
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
Mile Builder
Any Experience
Training
Caribbean Offshore Challenge
U.S. Virgin Islands & Grenada • Caribbean
Next: 14 - 23 January 2027
From
US$5,250
2 dates available
Runs in Jan
Any Experience
Racing & Performance
STIR - St Thomas International Regatta
U.S. Virgin Islands • Caribbean
Next: 7 - 11 April 2027
From
—
1 date available
Runs in Apr
See All
Extraordinary sailing adventures for everyone
Browse trips chosen by sailors for sailors - no signup needed
Vetted operators only
Secure booking
Trusted by 40,000+ sailors
4 trips found
List
Map
vi
Sailing Type
Experience Level
Dates
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
Mile Builder
Any Experience
Training
Caribbean Offshore Challenge
U.S. Virgin Islands & Grenada • Caribbean
Next: 14 - 23 January 2027
From
US$5,250
2 dates available
Runs in Jan
Any Experience
Racing & Performance
STIR - St Thomas International Regatta
U.S. Virgin Islands • Caribbean
Next: 7 - 11 April 2027
From
—
1 date available
Runs in Apr
See All
