boating vacations
Experience a Sailing Vacation outside Canada.
Join us for a Vacation Flotilla, Sailing Course, Mileage Builder, or Skippered Charter. Already an experienced sailor? We’ll help you arrange the perfect Bareboat Charter anywhere in the world.
The Best Week of Your Life Starts Here!
Imagine spending a week sailing crystal-clear waters, discovering secluded anchorages, snorkeling vibrant reefs, and sharing unforgettable sunsets with fellow sailors. No, this isn’t a dream—it’s an Advantage Boating Caribbean Sailing Vacation waiting for you!
For over three decades, sailors from across Canada have chosen Advantage Boating to experience the trip of a lifetime. Whether you’re crossing an item off your bucket list or have a lifelong passion for sailing, you’ll leave with new skills, new confidence, and stories you’ll be telling for years.
Explore our 2027 Caribbean Sailing Vacation Course opportunities below and discover why sailors return year after year.
With courses for every experience level, there’s never been a better time to trade winter for warm trade winds, turquoise waters, and an unforgettable week under sail.
2027 Winter Caribbean Sailing Opportunities.
Whether you’re pursuing certification, eyeing your first bareboat adventure, or just want to sail in good company, we have a down-south opportunity that’s right for you. From Basic Cruising to Intermediate, Advanced, and even ICC certification—our Winter Caribbean Sailing Courses are designed for all levels and are taught by experienced, Sail Canada-certified instructors aboard fully equipped yachts.
Explore our 2027 Winter Sailing Opportunities below.
Leave behind the snow shovels this winter and set course for the British Virgin Islands with Advantage Boating!
Escape winter and join us in the British Virgin Islands this January or February for an unforgettable week of sailing, learning, and island adventure!
Whether you’re looking to earn your Basic, Intermediate, or Advanced Sail Canada certification, or build valuable offshore experience through our Mileage Builder program, there’s a Caribbean Sailing Vacation Course for you. Courses run weekly from late January to the end of February 2027 and pricing starts at $2,895 USD per person (based on double occupancy).
Spaces are limited and our BVI vacation sailing courses fill quickly each year, so don’t wait! Download the full brochure and application form here, once completed, email it to us at info@advantageboating.com to secure your spot on this once-in-a-lifetime sailing experience. We can’t wait to welcome you aboard and share the beauty of the British Virgin Islands with you!
Where Will Your Next Adventure Take You?
Whether you’re looking to earn your Sail Canada certification, build offshore experience, or charter your own yacht, we have an unforgettable Caribbean adventure waiting for you!
Caribbean Sailing Vacation Courses
Flotillas and Mileage Builders
