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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

24 Trips

Mile Builder
Any ExperienceRacing & Performance

Malta to Cartagena Mile Builder

Malta & Spain • Europe
Next: 25 - 29 October 2026
From
—
2 dates available
Runs Oct - Oct
ARC
Intermediate & AdvancedRacing & Performance

Atlantic Rally for Cruisers (ARC)

Spain & St. Lucia • Europe
Next: 29 November - 18 December 2026
From
—
1 date available
Runs in Nov
Atlantic
Any ExperienceRacing & Performance

RORC Transatlantic Race

Spain & Antigua & Barbuda • Europe
Next: 7 - 20 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
Any ExperienceRacing & Performance

Grenada Sailing Week

Grenada • Caribbean
Next: 31 January - 5 February 2027
From
—
1 date available
Runs in Jan
RORC
Intermediate & AdvancedRacing & Performance

RORC Caribbean 600

Antigua & Barbuda • Caribbean
Next: 16 - 23 February 2027
From
—
1 date available
Runs in Feb
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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

24 trips found

Mile Builder
Any ExperienceRacing & Performance

Malta to Cartagena Mile Builder

Malta & Spain • Europe
Next: 25 - 29 October 2026
From
—
2 dates available
Runs Oct - Oct
ARC
Intermediate & AdvancedRacing & Performance

Atlantic Rally for Cruisers (ARC)

Spain & St. Lucia • Europe
Next: 29 November - 18 December 2026
From
—
1 date available
Runs in Nov
Atlantic
Any ExperienceRacing & Performance

RORC Transatlantic Race

Spain & Antigua & Barbuda • Europe
Next: 7 - 20 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
Any ExperienceRacing & Performance

Grenada Sailing Week

Grenada • Caribbean
Next: 31 January - 5 February 2027
From
—
1 date available
Runs in Jan
RORC
Intermediate & AdvancedRacing & Performance

RORC Caribbean 600

Antigua & Barbuda • Caribbean
Next: 16 - 23 February 2027
From
—
1 date available
Runs in Feb
RORC
Intermediate & AdvancedRacing & Performance

RORC Caribbean 600

Antigua & Barbuda • Caribbean
Next: 17 - 26 February 2027
From
—
1 date available
Runs in Feb
RORC
Any ExperienceRacing & Performance

RORC Caribbean 600

Antigua & Barbuda • Caribbean
Next: 19 - 26 February 2027
From
—
1 date available
Runs in Feb
Mile Builder
Any ExperienceRacing & Performance

Antigua - St. Maarten Mile Builder

Antigua & Barbuda & Sint Maarten • Caribbean
Next: 27 - 28 February 2027
From
—
1 date available
Runs in Feb
Any ExperienceRacing & Performance

Heineken Regatta – Sint Maarten

Sint Maarten • Caribbean
Next: 3 - 8 March 2027
From
—
1 date available
Runs in Mar
Mile Builder
Any ExperienceRacing & Performance

St. Maarten - Antigua Mile Builder

Sint Maarten & Antigua & Barbuda • Caribbean
Next: 8 - 9 March 2027
From
—
1 date available
Runs in Mar
Any ExperienceRacing & Performance

Antigua Racing Cup

Antigua & Barbuda • Caribbean
Next: 17 - 21 March 2027
From
—
1 date available
Runs in Mar
Any ExperienceRacing & Performance

STIR - St Thomas International Regatta

U.S. Virgin Islands • Caribbean
Next: 7 - 11 April 2027
From
—
1 date available
Runs in Apr
Mile Builder
Any ExperienceRacing & Performance

Horta - Vigo Mile Builder

Portugal & Spain • Europe
Next: 8 - 12 April 2027
From
—
1 date available
Runs in Apr
Any ExperienceRacing & Performance

Antigua Sailing Week

Antigua & Barbuda • Caribbean
Next: 19 - 25 April 2027
From
—
1 date available
Runs in Apr
Beginner & IntermediateRacing & Performance

Antigua Sailing Week

Antigua & Barbuda • Caribbean
Next: 19 - 23 April 2027
From
—
1 date available
Runs in Apr
Mile Builder
Any ExperienceRacing & Performance

Vigo - Cowes Mile Builder

Spain & United Kingdom • Europe
Next: 19 - 23 June 2027
From
—
1 date available
Runs in Jun
Fastnet
Any ExperienceRacing & Performance

Rolex Fastnet Race

United Kingdom & France • Europe
Next: 20 - 27 July 2027
From
—
1 date available
Runs in Jul
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