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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
11 Trips
sx
Sailing Type
Experience Level
Dates
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
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
Any Experience
Racing & Performance
Heineken Regatta – Sint Maarten
Sint Maarten • Caribbean
Next: 3 - 8 March 2027
From
—
1 date available
Runs in Mar
Mile Builder
Any Experience
Racing & Performance
St. Maarten - Antigua Mile Builder
Sint Maarten & Antigua & Barbuda • Caribbean
Next: 8 - 9 March 2027
From
—
1 date available
Runs in Mar
Any Experience
Training
Eastern Caribbean Passage
Grenada & Sint Maarten • Caribbean
Next: 12 - 20 March 2027
From
US$4,850
1 date available
Runs in Mar
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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
11 trips found
List
Map
sx
Sailing Type
Experience Level
Dates
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
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
Any Experience
Racing & Performance
Heineken Regatta – Sint Maarten
Sint Maarten • Caribbean
Next: 3 - 8 March 2027
From
—
1 date available
Runs in Mar
Mile Builder
Any Experience
Racing & Performance
St. Maarten - Antigua Mile Builder
Sint Maarten & Antigua & Barbuda • Caribbean
Next: 8 - 9 March 2027
From
—
1 date available
Runs in Mar
Any Experience
Training
Eastern Caribbean Passage
Grenada & Sint Maarten • Caribbean
Next: 12 - 20 March 2027
From
US$4,850
1 date available
Runs in Mar
Any Experience
Cruising
Caribbean Hang Out Cruise - St Maarten to Antigua
Sint Maarten & Antigua & Barbuda • Caribbean
Next: 19 - 26 March 2027
From
—
1 date available
Runs in Mar
Mile Builder
Any Experience
Training
Caribbean Offshore Intensive
Sint Maarten & Grenada • Caribbean
Next: 27 March - 3 April 2027
From
US$4,850
1 date available
Runs in Mar
Mile Builder
Any Experience
Training
Rum & Ruins Passage
Sint Maarten • Caribbean
Next: 10 - 17 April 2027
From
US$4,850
1 date available
Runs in Apr
ARC
Advanced & Intermediate
Expedition
Atlantic Crossing Caribbean to Europe
Sint Maarten & France • Caribbean
Next: 1 May - 3 June 2027
From
—
1 date available
Runs in May
Mile Builder
Any Experience
Training
North Atlantic Intensive
Sint Maarten & Bermuda • Caribbean
Next: 6 - 15 May 2027
From
US$7,750
1 date available
Runs in May
See All
