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.
2026 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 2026 Winter Sailing Opportunities below.
Leave behind the snow shovels this winter and set course for the British Virgin Islands with Advantage Boating!
This February, join Advantage Boating for an unforgettable 8-day sailing experience in the breathtaking British Virgin Islands. Perfect for vacationers and sailors looking to build skills or earn certification, our Caribbean Sailing Vacation Courses support every level, from Basic Cruising to Intermediate, Advanced, and ICC certification.
Courses run weekly from late January to the end of February 2026 and pricing starts at $2,795 USD per person (based on double occupancy).
Spaces are limited and filling quickly. Download the full brochure and apply online today to secure your place on this once-in-a-lifetime sailing experience.
Freedom, Fun, and a Fleet of Friends! Explore Paradise by Sail – Flotilla Style!
Independent sailing, shared adventure—flotillas are better together! This winter, build the skills and sea time to sail confidently with catamaran and monohull options!
Join us from March 21–28, 2026, for an unforgettable 8-day sailing experience through the stunning islands of the Abacos. This fun and social flotilla is designed for sailors and vacationers alike, offering the perfect mix of skill-building and laid-back island adventure.
The Bahamas are a sailor’s dream—steady trade winds, turquoise waters, and endless opportunities to snorkel, swim, and soak in authentic Bahamian culture. With 3-4 boats, a mix of catamarn and monohull boat options and 3–5 hours of sailing each day, participants will also enjoy plenty of time for beach stops, local exploring, and group socials.
Whether you’re looking to log miles, connect with fellow sailors, or simply relax in paradise, the Abacos Flotilla offers a well-balanced blend of learning, leisure, and discovery.
For full details and to fill out your application, CLICK HERE.
50,000 Shades of Blue – Your Adventure awaits!
Enjoy a more intimate sailing experience through the pristine waters of the Exumas aboard a fully equipped Catalina-Morgan 440. Fully custom 1-2+ week sailing vacation for just 2 – 3 people, this skippered charter and sailing-lifestlye experience tailored entirely to you. With a relaxed, adventurous itinerary designed to explore the very best that the Exumas has to offer. A perfect balance of adventure and relaxation.
For full details and to fill out your application, CLICK HERE.
Caribbean Sailing Vacation Courses
Flotillas and Mileage Builders
