…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

Adventure
From $3,295

Easter Whistlestop Milebuilding Sailing Adventure - 5th to 18th April 2020

10 Days, 9 nights
Antigua & Barbuda, Guadeloupe, St Barth’s, St Martin/St Maarten
FULL
From $1,025

Mediterranean Sailing Holiday in the Gulf of Fethiye - 7th to 14th September 2019

7 Days/Nights
Turkey
FULL
From $2,795

Thanksgiving Sailing in St Martin, St Barths & Anguilla - 23rd November to 2nd December 2019

10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
Special Event
From $3,495

Caribbean Christmas & New Year Sailing + Carnivale - 22nd December 2019 to 4th January 2020

14 Days, 13 Nights
Anguilla, St Barth’s, St Eustatius, St Kitts & Nevis, St Martin/St Maarten
For Beginners
From $2,795

Beginner Sailing in St Martin, St Barths & Anguilla - 10th to 19th January 2020

10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
Adventure
From $2,795

Caribbean Sailing Adventure From St Maarten to Guadeloupe - 31st January to 9th February 2020

10 Days, 9 nights
Guadeloupe, Montserrat, St Barth’s, St Kitts & Nevis, St Martin/St Maarten
Adventure
From $2,795

Adventure Sailing From Guadeloupe to St Martin - 14th to 23rd February 2020

10 Days, 9 nights
Antigua & Barbuda, Guadeloupe, St Barth’s, St Martin/St Maarten
Special Event
From $2,895

Sail in St Martin, St Barth's & Anguilla; Spectate the St Barth's Bucket Regatta - 14th to 23rd March 2020

10 Days, 9 nights
Anguilla, St Barth’s, St Martin/St Maarten
For Beginners
From $2,795

Caribbean Sailing Holiday in the British Virgin Islands - 1st to 10th May 2020

10 Days, 9 nights
British Virgin Islands
For Beginners
From $2,795

Sailing Holiday in the British Virgin Islands - 16th to 25th May 2020

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

2018-19 Caribbean Sailing Areas

Anguilla
Anguilla
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
Read more

What Our Guests Say...

Jimmy McLeanJimmy McLeanWinston-Salem, NC USA

I just completed the whistle stop trip on Ibis, with Sam captaining. Three other guys and I served as "crew". For me , this was the trip of a lifetime. We sailed about 450 miles in mostly great conditions. I learned a bunch about cruising.
We did 3 night sails. Sam and Neil scheduled several shore days for us. They lined up some great activities.
The food was wonderful. The company was a blast. I got a year's worth of laughter in.