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.

Our Mission is Simple—To provide a worry-free and unforgettable vacation.

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.

Upcoming Flotilla Adventures

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