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 Dodecanese islands in the heart of the Aegean Sea.

     👉 Detailed Greece Brochure [CLICK HERE]

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.

Abacos Flotilla Enrolment Form
Greece Flotilla Enrolment Form

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

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

Flotilla & Mileage Builder yacht charter costs explained

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.

 

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