…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

pirate party invite
Special Event
From $0

Pirate Parley 17th September 2016 - Kingston Upon Thames, UK

A few hours
London
sailing holidays in anguilla (3 of 3)-2
For Beginners
From $1,595

Sailing Holiday in St Martin, St Barths & Anguilla - 11th November to 20th November 2016

10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
sailing holidays in paradise (1 of 1)-41
Experienced
From $1,795

Whistlestop Sailing Tour of the Leeward Islands - 27th November to 10th December 2016

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
From $1,995

Caribbean Christmas & New Year Sailing in the Virgin Islands - 22nd December 2016 to 4th January 2017

14 Days, 13 Nights
British Virgin Islands, US Virgin Islands
_H3B4719
For Beginners
From $1,595

Caribbean Sailing Holiday in the British Virgin Islands - 13th January to 22nd January 2017

10 Days, 9 nights
British Virgin Islands
sailing holidays in st kitts nevis (1 of 1)
Adventure
From $1,695

Sailing Holiday in St Kitts and Nevis, St Barths & Anguilla - 27th January to 7th February 2017

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
From $1,595

Sailing Holiday in St Martin, St Barths & Anguilla - 11th February to 20th February 2017

10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
heineken
Regatta
From $1,695

Sail as Race Crew in the St Maarten Heineken Regatta - 25th February to 6th March 2017

10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
StBarthB
Special Event
From $1,595

Sail in St Martin, St Barth's & Anguilla including the St Barth's Bucket Regatta - 11th to 20th March 2017

10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
sailing holidays in paradise (1 of 1)-40
Adventure
From $1,595

Caribbean Adventure Sailing From St Maarten to Guadeloupe - 24th March to 2nd April 2017

10 Days, 9 nights
Guadeloupe, Montserrat, St Barth’s, St Kitts & Nevis, St Martin/St Maarten
sailing holidays in dominica (3 of 5)
Adventure
From $1,795

Easter Sailing Holiday in Guadeloupe, the Saints, Marie Galante & Dominica - 9th to 22nd April 2017

14 Days, 13 Nights
Dominica, Guadeloupe, Marie Galante, The Saintes
sailing holidays in st lucia (1 of 1)-1
Adventure
From $1,595

Sailing Holiday in Dominica, Martinique & St Lucia - 28th April to 7th May 2017

10 Days, 9 nights
Dominica, Martinique, St Lucia
DCIM100GOPROGOPR6749.
Adventure
From $1,595

Sailing Holiday in St Lucia, the Grenadines & Grenada - 13th to 22nd May 2017

10 Days, 9 nights
Grenada, St Lucia, St Vincent, The Grenadines
sailing in st vincent grenadines (24 of 24)
For Beginners
From $1,595

Sailing Holiday in Paradise; Grenada & the Grenadines - 27th May to 5th June 2017

10 Days, 9 nights
Grenada, The Grenadines, Tobago Cays
sailing in trinidad & tobago (102 of 155)
Experienced
From $1,695

Adventure Sailing Holiday to the Grenadines, Trinidad & Tobago- 9th to 20th June 2017

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

From the Ship's Log

whistlestop caribbean (1 of 1)-1

Whistlestop Caribbean Milebuilder Sailing Trip - Nov 2015

Read more

What Our Guests Say...

Andrew SwayneAndrew SwayneUK

I had a great time.

Sam is an excellent sailor, host and chef.