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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

72 Trips

Any ExperienceCruising

October Half Term Corfu & Paxos - Share-a-Yacht

Greece • Europe
Next: 25 October - 1 November 2026
From
—18% off
2 dates available
Runs Oct - Oct
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
Intermediate & BeginnerTraining

RYA Day Skipper Practical

United Kingdom • Europe
Next: 26 - 30 October 2026
From
—
9 dates available
Runs Oct - Mar
BeginnerTraining

RYA Competent Crew

United Kingdom • Europe
Next: 28 October - 1 November 2026
From
—
9 dates available
Runs Oct - Mar
Any ExperienceTraining

Croisière Formation FFV dans les Grenadines

Martinique • Caribbean
Next: 7 - 14 November 2026
From
—
15 dates available
Runs Nov - May
Mile Builder
Any ExperienceTraining

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
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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

72 trips found

Any ExperienceCruising

October Half Term Corfu & Paxos - Share-a-Yacht

Greece • Europe
Next: 25 October - 1 November 2026
From
—18% off
2 dates available
Runs Oct - Oct
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
Intermediate & BeginnerTraining

RYA Day Skipper Practical

United Kingdom • Europe
Next: 26 - 30 October 2026
From
—
9 dates available
Runs Oct - Mar
BeginnerTraining

RYA Competent Crew

United Kingdom • Europe
Next: 28 October - 1 November 2026
From
—
9 dates available
Runs Oct - Mar
Any ExperienceTraining

Croisière Formation FFV dans les Grenadines

Martinique • Caribbean
Next: 7 - 14 November 2026
From
—
15 dates available
Runs Nov - May
Mile Builder
Any ExperienceTraining

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
BeginnerExpedition

Coastal Passage: Monterey to San Francisco

United States • Americas
Next: 14 - 14 November 2026
From
US$600
1 date available
Runs in Nov
ARC
Any ExperienceExpedition

ARC Atlantic Crossing | Gran Canaria → St Lucia

Spain & St. Lucia • Europe
Next: 18 November - 20 December 2026
From
—
1 date available
Runs in Nov
ARC
Any ExperienceExpedition

ARC Atlantic Crossing – Canary Islands to Saint Lucia

Spain & St. Lucia • Europe
Next: 22 November - 13 December 2026
From
—
2 dates available
Runs Nov - Nov
Mile Builder
Any ExperienceTraining

Wind & Waves Seminar

U.S. Virgin Islands • Caribbean
Next: 3 - 7 December 2026
From
US$3,850
2 dates available
Runs in Dec
Beginner & IntermediateCruising

St Lucia Christmas Cruise

St. Lucia • Caribbean
Next: 19 - 26 December 2026
From
—20% off
1 date available
Runs in Dec
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
Atlantic
Any ExperienceRacing & Performance

RORC Transatlantic Race

Spain & Antigua & Barbuda • Europe
Next: 7 - 20 January 2027
From
—
1 date available
Runs in Jan
Any ExperienceExpedition

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 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 ExperienceExpedition

St. Vincent & Grenadines Expedition

St. Lucia • Caribbean
Next: 15 - 24 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
Mile Builder
Any ExperienceTraining

Windward to Leeward Training

Sint Maarten • Caribbean
Next: 30 January - 6 February 2027
From
US$5,200
1 date available
Runs in Jan
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