…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
sailingdominica (8 of 10)
Adventure
10 Days, 9 nights
Dominica, Martinique, St Lucia
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
US Virgin Islands
US Virgin Islands

What Our Guests Say...

Adrian HoldenAdrian HoldenNowich, UK

"Sam, just to say thankyou for an unforgettable 2 weeks on ibis 5 , never had so much fun standing up ! It was just perfect for me and managed to leave all me troubles and tribulations behind me, I really appreciated all the effort you put in to make it such a special time, keep up the good work, you have been an inspiration for my sailing practice !