Caribbean Sailing Vacations

Caribbean Sailing Vacations
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Caribbean Sailboat Charters aboard the 50 foot Luxury Sailing Yacht "Sophisticated Lady"...
Looking for the most fun you can have on a Caribbean Vacation?   Try a Charter Sailboat in the exquisite British Virgin Islands, the most spectacular sailing grounds in the Caribbean!  We offer fully crewed charters, or if you'd prefer, one of our Share-the-Sail Adventures will certainly give you something to write home about!

Swim, sail, snorkel, relax in the sun, explore beaches and remote islands ~ whatever your heart desires!

Enjoy, spectacular views and an unforgettable adventure aboard a private charter sailboat in some of the most pristine sailing areas found anywhere in the Caribbean!.

Let us create the perfect
Caribbean sailing vacation for you!

Caribbean Sailboat Vacations
Caribbean Sailboat Charters





Live BoatCam from 'Sophisticated Lady' in the Caribbean!

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Video of 'Lucky' the Talking Parrot!
View our Liveaboard Pirate Parrot 'Lucky'
She will entertain you endlessly with her antics during your stay!



Sailing Vacations in the British Virgin Islands


Caribbean Sailing Vacations, Sailboat Charters, and Share-the-Sail Adventures!


Romantic private charters

Swim, snorkel & scuba dive

Incredible sailing adventures

Toronto Boat Cruises

Explore beautiful, exotic places

Yoga Retreats in the Caribbean!!
Latest News

Early Booking Specials for 2014 Share-the-Sail Cabins
Enquire Here For Details!

BackStage BVI's DVD!

A behind the scenes look at some of the people, places, and things that make these islands special! Look for a sneak peak on our new movie page!
Send your request here for more info!

NEWS!!  'Sophisticated Lady' now offering Sailing Adventures in Grenada and the Grenadines during the summer months!!


Offshore Sailing Adventures



Wind in my Sails Inc.

Caribbean Cell: (284) 545-0911
Skype ID: WindInMySails