flotilla sailing
Flotilla Getaway
Explore. Sail. Relax. Repeat.
Join Advantage Boating for a sailing vacation like no other! For over 25 years, we have been hosting unforgettable flotilla vacations in some of the world’s most beautiful sailing destinations — including Greece, Croatia, Thailand, and the Caribbean.
Whether you’re new to sailing or a seasoned cruiser, we make it easy to discover the world — one incredible voyage at a time.
What is a Flotilla?
At its core, a flotilla is a fleet of sailboats traveling together—each with its own crew—under the guidance of a knowledgeable lead boat and flotilla leader. As Skipper or crew you command your own vessel, but you never sail alone: there’s always support for navigation, weather updates, and mooring assistance. These trips bring together the freedom of a bareboat charter with the comfort, confidence, and social spark of group travel.
Our Mission is Simple—To Provide a Worry-Free and Unforgettable Vacation
Upcoming Flotilla Adventures
Our flotilla trips sell out fast. To reserve your spot, please see below— we’d love to welcome you aboard!
Abacos, Bahamas 🇧🇸
Join us March 21–28, 2026, for an unforgettable sailing adventure through the stunning islands of the Abacos—a fun and social way to sail.
👉 Detailed Bahamas Brochure [CLICK HERE]
Greece 🇬🇷
Set sail September 5–19, 2026, exploring the breathtaking Cyclades islands in the heart of the Aegean Sea.
👉 Detailed Greece Brochure Coming Soon.
How Do I Register?
- Download our Flotilla Enrolment Form.
- Complete and sign the Brochure/Application form and email it back to us at info@advantageboating.com
- We will contact you to confirm your enrolment.
Sail with Confidence through breathtaking destinations—whether you’re an experienced skipper or new to sailing, you’ll enjoy the support of a lead boat, daily briefings, and guidance from our experienced team as you cruise turquoise waters, island-hop to charming harbours, and unwind in warm, waterfront villages.
Sail side-by-side with fellow cruisers, discover stunning destinations, and enjoy a perfect balance of independence and community—ideal for couples, single sailors, or friends.
Recommended Experience
- As Crew – Sail Canada Basic Cruising standard or equivalent.
- As Skipper – Sail Canada Intermediate Cruising, VHF-ROC(M), ICC (for Greece & Croatia), and previous skipper experience.
- Please contact us at info@advantageboating.com or 613-721-8683 for more information.
Robert and I want to thank Doris and Ron for a great introduction to cruising. Sailing in the Caribbean is so beautiful, and swimming in that clear turquoise water was a real treat. Well planned, well executed, it was a terrific vacation. We are definitely hooked. ~ S. McKellips and R. Madill, Ottawa, February 2017
Do you want to know what our sailing vacations are like? Check out this video from our Windward Islands trip in 2020:
What makes our trips different?
Here’s Why You Should Join an Advantage Boating Flotilla.
⛵ 25+ Years of Experience — We have a proven track record of delivering unforgettable sailing vacations in top destinations around the world — from the Caribbean to Greece, Croatia, and beyond.
⛵ Expertly Planned Itineraries — Let us handle the details! We arrange the boats, plan the routes, organize logistics, highlight local hotspots, and safely guide you from one stunning anchorage to the next.
⛵ On-the-Water Support — Our lead boat and experienced flotilla leaders are on site and sailing with you — offering guidance, assistance, and peace of mind from arrival at the charter base to the moment you disembark.
⛵ Certified Skippers on Board — Each boat will has a certified skipper and co-skipper, so newer sailors can enjoy the experience knowing you’re in safe, capable hands.
⛵ Flexible Crew Options —Travel solo, as a couple, or with friends — we help match crews and boats to create the best experience for everyone on board.
⛵ Stress-Free Provisioning — We’ve perfected the provisioning process so you can skip the stress and start enjoying your vacation from day one.
⛵ Exceptional Yachts — We charter only modern, well-equipped monohulls and catamarans ranging from 40–54 feet (3–5 cabins), offering comfort, style, and performance.
⛵ Mileage Builder Options Available — Looking to log more sea miles or boost your sailing skills? Our Mileage Builder weeks include longer passages, open-water sailing, and overnights for a more advanced sailing experience.
⛵ Sailing-Centric, Start to Finish — We specialize in delivering sailing-focused vacations, with personalized support every step of the way — from booking to boarding and beyond.
Previous Flotilla Adventures
Recently, Advantage Boating hosted flotillas & mileage builders and spent:
- 3 months in the Bahamas in 2025 hosting mileage builders & sailing lifestyle experiences.
- 3 months in the Bahamas in 2024 hosting mileage builders & sailing lifestyle experiences.
- 2 weeks in Croatia with 30 sailors in 2024
- 2 weeks in Greece with 48 sailors in 2023
- 3 weeks in the Windward Islands with 40 sailors in 2023.
- 5 weeks in the Windward Islands with 58 sailors in 2020.
- 5 weeks in the Leeward Islands with 64 sailors in 2019.
- 2 weeks in Croatia with 30 sailors in 2018.
- 4 weeks in the Grenadines with 60 sailors in 2018.
Our Mission is Simple—To Provide a Worry-Free and Unforgettable Vacation
Sail side-by-side with fellow cruisers, discover stunning destinations, and enjoy a perfect balance of independence and community—ideal for couples, single sailors, or friends.