…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

sailing holidays in anguilla (3 of 3)-2
For Beginners
10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
sailing holidays in paradise (1 of 1)-41
Experienced
14 Days, 13 Nights
Anguilla, Antigua & Barbuda, Guadeloupe, Montserrat, St Barth’s, St Eustatius, St Kitts & Nevis, St Martin/St Maarten
christmas in paradise (1 of 1)-1
Special Event
14 Days, 13 Nights
British Virgin Islands, US Virgin Islands
sailing holidays in st kitts nevis (1 of 1)
Adventure
12 Days, 11 Nights
Anguilla, St Barth’s, St Eustatius, St Kitts & Nevis, St Martin/St Maarten
sailing holidays in anguilla (3 of 3)-1
For Beginners
10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
heineken
Regatta
10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
StBarthB
Special Event
10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
sailing holidays in paradise (1 of 1)-40
Adventure
10 Days, 9 nights
Guadeloupe, Montserrat, St Barth’s, St Kitts & Nevis, St Martin/St Maarten
sailing holidays in dominica (3 of 5)
Adventure
14 Days, 13 Nights
Dominica, Guadeloupe, Marie Galante, The Saintes
sailing holidays in st lucia (1 of 1)-1
Adventure
10 Days, 9 nights
Dominica, Martinique, St Lucia
DCIM100GOPROGOPR6749.
Adventure
10 Days, 9 nights
Grenada, St Lucia, St Vincent, The Grenadines
sailing in st vincent grenadines (24 of 24)
For Beginners
10 Days, 9 nights
Grenada, The Grenadines, Tobago Cays
sailing in trinidad & tobago (102 of 155)
Experienced
12 Days, 11 Nights
Grenada, The Grenadines, Tobago, Trinidad
Choose a

Caribbean Sailing Area

Anguilla
Anguilla
Antigua & Barbuda
Antigua & Barbuda
British Virgin Islands
British Virgin Islands
Dominica
Dominica
Grenada & Carriacou
Grenada & Carriacou
Grenadines & Tobago Cays
Grenadines & Tobago Cays
Guadeloupe
Guadeloupe
Martinique
Martinique
Montserrat
Montserrat
St Barth's
St Barth's
St Kitts & Nevis
St Kitts & Nevis
St Lucia
St Lucia
St Martin/St Maarten
St Martin/St Maarten
St Vincent & the Grenadines
St Vincent & the Grenadines
Trinidad & Tobago
Trinidad & Tobago
US Virgin Islands
US Virgin Islands

What Our Guests Say...

Andrew SwayneAndrew SwayneUK

I had a great time.

Sam is an excellent sailor, host and chef.