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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
20 Trips
Location
Expedition
Experience Level
Dates
Intermediate & Advanced
Expedition
Pacific Crossing - Hawaii to California
United States • Americas
Next: 10 - 27 September 2026
From
US$8,000
1 date available
Runs in Sept
Yachtmaster
Intermediate & Advanced
Expedition
Trip from Lagos, Portugal to Las Palmas de Gran Canaria
Portugal & Spain • Europe
Next: 4 - 11 October 2026
From
—
1 date available
Runs in Oct
Advanced
Expedition
Master the Passage: Pula to Malta Offshore
Croatia & Malta • Europe
Next: 5 - 12 October 2026
From
—
1 date available
Runs in Oct
Intermediate & Advanced
Expedition
Biscay Bound – Dartmouth to Porto Offshore Passage
United Kingdom & Portugal • Europe
Next: 5 - 15 October 2026
From
—
1 date available
Runs in Oct
Intermediate & Advanced
Expedition
South Atlantic Expedition - Leg 2
St. Helena & South Africa • Indian Ocean
Next: 11 - 21 November 2026
From
—
5 dates available
Runs Oct - Nov
Any Experience
Expedition
South Atlantic Expedition - Leg 1
South Africa & St. Helena • Indian Ocean
Next: 12 - 22 November 2026
From
—
5 dates available
Runs Oct - Oct
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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
20 trips found
List
Map
Location
Expedition
Experience Level
Dates
Intermediate & Advanced
Expedition
Pacific Crossing - Hawaii to California
United States • Americas
Next: 10 - 27 September 2026
From
US$8,000
1 date available
Runs in Sept
Yachtmaster
Intermediate & Advanced
Expedition
Trip from Lagos, Portugal to Las Palmas de Gran Canaria
Portugal & Spain • Europe
Next: 4 - 11 October 2026
From
—
1 date available
Runs in Oct
Advanced
Expedition
Master the Passage: Pula to Malta Offshore
Croatia & Malta • Europe
Next: 5 - 12 October 2026
From
—
1 date available
Runs in Oct
Intermediate & Advanced
Expedition
Biscay Bound – Dartmouth to Porto Offshore Passage
United Kingdom & Portugal • Europe
Next: 5 - 15 October 2026
From
—
1 date available
Runs in Oct
Intermediate & Advanced
Expedition
South Atlantic Expedition - Leg 2
St. Helena & South Africa • Indian Ocean
Next: 11 - 21 November 2026
From
—
5 dates available
Runs Oct - Nov
Any Experience
Expedition
South Atlantic Expedition - Leg 1
South Africa & St. Helena • Indian Ocean
Next: 12 - 22 November 2026
From
—
5 dates available
Runs Oct - Oct
Any Experience
Expedition
Across the Bay of Biscay | Portsmouth → Gran Canaria
United Kingdom & Spain • Europe
Next: 17 - 6 November 2026
From
—
1 date available
Runs in Oct
Any Experience
Expedition
ARC Atlantic Crossing | Gran Canaria → St Lucia
Spain & St. Lucia • Europe
Next: 18 - 20 December 2026
From
—
1 date available
Runs in Nov
Any Experience
Expedition
ARC Atlantic Crossing – Canary Islands to Saint Lucia
Spain & St. Lucia • Europe
Next: 22 - 13 December 2026
From
—
2 dates available
Runs Nov - Nov
Beginner
Expedition
South Atlantic crossing: Cape Town -- Rio
South Africa • Indian Ocean
Next: 1 - 20 December 2026
From
—
1 date available
Runs in Dec
Any Experience
Expedition
Race and Explore the Southern Caribbean
Antigua & Barbuda • Caribbean
Next: 13 - 8 February 2027
From
—
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
Expedition
Salvador - Rio De Janeiro Offshore
Brazil • Americas
Next: 15 - 26 March 2027
From
—
1 date available
Runs in Mar
ARC
Intermediate & Advanced
Expedition
The Atlantic Homecoming Voyage – West to East
Antigua & Barbuda & United Kingdom • Caribbean
Next: 10 - 15 May 2027
From
—
1 date available
Runs in Apr
ARC
Any Experience
Expedition
Atlantic Crossing Caribbean to Europe
Sint Maarten & Portugal • Caribbean
Next: 1 - 6 June 2027
From
—
1 date available
Runs in May
Any Experience
Expedition
Madagascar to Zanzibar
Madagascar & Tanzania • Indian Ocean
Next: 3 - 19 May 2027
From
—
1 date available
Runs in May
Intermediate & Beginner
Expedition
Kiel to Copenhagen - Leg 1 of our tour of the Baltics
Germany & Denmark • Europe
Next: 29 - 7 June 2027
From
—
1 date available
Runs in May
Scotland
Any Experience
Expedition
Sail the Northcoast 500 Scotland
United Kingdom • Europe
Next: 19 - 20 July 2027
From
—
1 date available
Runs in Jun
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