…because LIFE is about the journey,

and TIME the only real currency we have…

Find Your Perfect Caribbean Sailing Vacation...

For singles, couples and solo travellers

Our Caribbean Sailing Holidays

For Beginners
From $2,595

Sailing Holiday in St Martin, St Barths & Anguilla - 16th February to 25th February 2019

10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
Adventure
From $2,595

Sailing Holiday in St Kitts and Nevis, St Barths & Statia - 2nd to 11th March 2019

10 Days, 9 nights
St Barth’s, St Eustatius, St Kitts & Nevis, St Martin/St Maarten
Special Event
From $2,695

Sail in St Martin, St Barth's & Anguilla; Spectate the St Barth's Bucket Regatta - 16th to 25th March 2019

10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
Adventure
From $2,595

Caribbean Adventure Sailing From St Maarten to Guadeloupe - 30th March to 8th April 2019

10 Days, 9 nights
Guadeloupe, Montserrat, St Barth’s, St Kitts & Nevis, St Martin/St Maarten
Adventure
From $2,595

Easter Sailing From Guadeloupe to St Martin - 13th to 22nd April 2019

10 Days, 9 nights
Antigua & Barbuda, Guadeloupe, St Barth’s, St Martin/St Maarten
For Beginners
From $2,595

Caribbean Sailing Holiday in the British Virgin Islands - 4th to 13th May 2019

10 Days, 9 nights
British Virgin Islands
For Beginners
From $2,595

Sailing Holiday in the British Virgin Islands - 25th May to 3rd June 2019

10 Days, 9 nights
British Virgin Islands
Choose one of our

2018-19 Caribbean Sailing Areas

Antigua & Barbuda
Antigua & Barbuda
British Virgin Islands
British Virgin Islands
Guadeloupe
Guadeloupe
Montserrat
Montserrat
St Barth's
St Barth's
St Kitts, Nevis & St Eustatius
St Kitts, Nevis & St Eustatius
St Martin/St Maarten, St Barth's & Anguilla
St Martin/St Maarten, St Barth's & Anguilla

From the Ship's Log

Sailing Milebuilder from the Bahamas to Cuba - Feb 2018

Some challenging weather at the start, gave way to some wonderful trade wind sailing and gave us 4 days exploring the beautiful beaches of Long
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What Our Guests Say...

Scott MacklinScott MacklinUSA

Sam, thank you for a wonderful vacation. Excellent hospitality, food was fantastic and all of your sailing knowledge.  God willing I will sail with you again!