We’ve been hosting flotilla adventures around the world for over 25 years!



Don’t worry about chartering the boat, assembling the crew or planning the route.  Our experienced flotilla leaders will organize the trip, help you plan the provisioning and provide you with all the information you will need for your adventure. Together with your crew, you will do the sailing while your flotilla guide leads you to the next breathtaking destination of the day. Support is always nearby





Everyone is involved at every stage according to the level of experience, so you will never be bored. Whether you’ve just completed your Basic Cruising or are an experienced sailor, you will deepen your sailing competencies, build confidence and get vital lessons in teamwork.







Recently, Advantage Boating hosted flotillas & mileage builders and spent:

      • 3 months in the Bahamas in 2024 hosting mileage builders & sailing lifestyle experiences
      • 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

Upcoming Trips:

  • Croatia Sept 2024
  • The Caribbean Jan – March 2025
  • Greece Sept 2025

Explore the Mediterranean and it’s exotic coastline and historical medieval towns!


1. CROATIA:  Croatia boasts the most stunning and sunniest coastlines in Europe.  From the base in Trogir, join us for a 14-day flotilla as we set sail and explore the crystal clear Adriatic waters.  With more than 1200 small Croatian islands to discover we will visit beautiful hidden bays accessible only by boat and explore charming seaside towns while immersing yourself in their rich history, culture and tradition.


How do I find out more?

  • Click on the image below to download our brochure and application for complete details about our trip.

How do I register for this trip?

  • Download our Croatia Brochure/Application form.
  • Complete and sign the above Croatia Brochure/Application form and email it back to us.
  • Submit a $500 USD holding deposit:  Holding deposit link.
  • We will contact you to confirm your enrolment.

Our flotilla vacations sell out quickly. 

Don’t miss the boat! Complete the application form for our upcoming trip or email us to secure your spot.


2. The Caribbean – Our 2024 winter sailing programs are sold out and we are planning for our winter 2025 winter sailing opportunities.  You can help us decide where to go next; let us know. The Windward Islands? The Leeward Islands?  BVIs?  Bahamas?  Send us an email and help us decide where Advantage Boating should sail winter 2025.

3. Greece – We sailed the impressive Cyclades islands of Greece in September 2023 and we can’t wait to go back again in September 2025.  Stay tuned for details!

Do you want to know what our sailing vacations are like?  Check out this video from our Windward Islands trip in 2020:

VIDEO:  Sailing the Windward Islands

What makes our trips different:

  • Proven track record:  25 years of delivering worldwide sailing vacations
  • Expert planners:  We arrange the boats, plan the routes, organize the details, locate the local hotspots and safely lead you from one beautiful anchorage to the next
  • On site sailing support:  Our lead boat and experienced flotilla leaders are there sailing with you to ensure a smooth trip from the day you arrive at the charter base to the day you disembark the boat
  • Certified skipper & co-skipper on each boat:  You can relax knowing you are in good hands
  • Crew planning:  Join our trips as a boat load, a couple or a single.   We organize the crew and boats to maximize a great experience for your trip
  • Easy provisioning:  We’ve perfected the process to take the stress out of provisioning
  • Exceptional boats:  We only use newer monohull & catamaran yachts ranging in size from 40- 52′ (3 – 5 cabin)
  • Mileage builder weeks are available:  For those who are looking for more of an instructional sailing experience, these trips including longer sailing stretches, more open water sailing and overnight sailing passages
  • Specialists in delivering sailing centric vacations:  We are with you every step of the way from start to finish

Providing a worry free & memorable vacation!

Your flotilla leaders


Recommended Experience:

Please contact us at info@advantageboating.com 613-721-8683 or toll free at 1-877-934-7245 for more information

Robert and I want to thank Doris and Ron for a great introduction to cruising.  The BVIs are 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 costs explained


For all our trips we encourage each participant to take out trip cancellation insurance should for some reason the trip not be able to take place. We are TICO (Travel Industry Council of Ontario) certified. Being part of TICO means we are tightly regulated for offering travel vacations. Sailing vacation fees are protected in that they go into a trust account. The boats we use are from Tier 1 charter companies. We will make every effort to protect your trip and will try to obtain refunds from the charter companies should any of our sailing vacations not be able to run due to for unforeseen circumstances.  You trips are protected through TICO and through the trip cancellation insurance we encourage you to take out. Advantage Boating has a longstanding record of offering and delivering sailing vacations for the past 25 years and prides itself from our excellent customer service.

*Note:  Advantage Boating reserves the right to alter program content, boat sizes or types and schedule due to situations beyond our control. Flights, land transfers and provisioning not included.  While Dufour, Beneteau and Jeanneau boats are the regular boats used in these programs, we reserve the right to substitute suitable yachts as necessary.  Catamaran options available.