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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
29 Trips
Location
Sailing Type
Experience Level
Dates
Mile Builder
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
Advanced & Intermediate
Expedition
The Three Seas Expedition: Pula to Sardinia
Croatia & Italy • Europe
Next: 13 - 23 December 2026
From
—
1 date available
Runs in Dec
Mile Builder
Intermediate & Advanced
Expedition
The Final Push Outwards: Sardinia to Gibraltar
Italy & Gibraltar • Europe
Next: 24 - 31 December 2026
From
—
1 date available
Runs in Dec
Mile Builder
Intermediate & Advanced
Expedition
The Atlantic Threshold: Gibraltar to the Canaries
Gibraltar & Spain • Europe
Next: 1 - 9 January 2027
From
—
1 date available
Runs in Jan
Mile Builder
Advanced
Expedition
Uphill to Brazil - 2200 NM Blue Water Passage
Martinique & Brazil • Caribbean
Next: 6 - 24 January 2027
From
—
1 date available
Runs in Jan
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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
29 trips found
List
Map
Location
Sailing Type
Experience Level
Dates
Mile Builder
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
Advanced & Intermediate
Expedition
The Three Seas Expedition: Pula to Sardinia
Croatia & Italy • Europe
Next: 13 - 23 December 2026
From
—
1 date available
Runs in Dec
Mile Builder
Intermediate & Advanced
Expedition
The Final Push Outwards: Sardinia to Gibraltar
Italy & Gibraltar • Europe
Next: 24 - 31 December 2026
From
—
1 date available
Runs in Dec
Mile Builder
Intermediate & Advanced
Expedition
The Atlantic Threshold: Gibraltar to the Canaries
Gibraltar & Spain • Europe
Next: 1 - 9 January 2027
From
—
1 date available
Runs in Jan
Mile Builder
Advanced
Expedition
Uphill to Brazil - 2200 NM Blue Water Passage
Martinique & Brazil • Caribbean
Next: 6 - 24 January 2027
From
—
1 date available
Runs in Jan
Mile Builder
Any Experience
Training
Caribbean Offshore Challenge
U.S. Virgin Islands & Grenada • Caribbean
Next: 14 - 23 January 2027
From
US$5,250
1 date available
Runs in Jan
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
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
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
Expedition
Darwin’s Passage | Panama City → Galapagos
Panama & Ecuador • Americas
Next: 2 - 11 April 2027
From
US$7,693
US$10,990
30% off
1 date available
Runs in Apr
Mile Builder
Any Experience
Racing & Performance
Horta - Vigo Mile Builder
Portugal & Spain • Europe
Next: 8 - 12 April 2027
From
—
1 date available
Runs in Apr
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
Mile Builder
Any Experience
Expedition
Trans-Pacific Passage | Galapagos → Marquesas
Ecuador & French Polynesia • Americas
Next: 16 April - 14 May 2027
From
US$9,233
US$13,190
30% off
1 date available
Runs in Apr
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
Mile Builder
Any Experience
Training
Gulf Stream Intensive
Bermuda & United States • Americas
Next: 21 - 29 May 2027
From
US$5,850
1 date available
Runs in May
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