Flotilla Getaway

The Pandemic has kept us from travelling, but won’t keep us grounded forever!  We are busy planning our next flotilla trips:

Upcoming Trips:

  • The Caribbean – February 2023
  • Greece – September 9-23, 2023
  • Croatia – September 7-21, 2024

Sailing Greece

Sailing the Caribbean


We’ve been hosting flotilla adventures around the world for over 20 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 breath-taking destination of the day.

Flotilla Sailing

Recently, Advantage Boating hosted flotillas and spent:

    • 5 weeks in the Windward Islands with 58 sailors in 2020 (Brochure)
    • 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

Check out this video from on of our Windward Islands trips:

VIDEO:  Sailing the Windward Islands

Upcoming Flotilla Trips:

  1. Caribbean – February 2023
  2. Greece – NEW DATES:  September 9-23, 2023 (2020 Greece Brochure) (2020 Greece Flotilla Application)
    Get ready for crystal clear blue waters, magnificent sunsets, warm breezes and dancing the night away.  This year, make your sailing holiday in Greece a reality. Sail away to discover the land of ancient lore and modern mysteries. Join us in Greece this September!
  3. Croatia – September 7-21, 2024

2022:  If you are interested sailing down south with us this winter, please send us an email @ info@advantageboating.com and we will reach out to you with additional information. 

Your flotilla leaders

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!

Our flotilla vacations sell out quickly. 

Don’t miss the boat! Complete the Greece 2023 application form or email us to secure your spot.




FORMS:  2020 Greece Flotilla Application.  (Please fill out and submit to info@advantageboating.com)

As Crew – Sail Canada Basic Cruising standard or equivalent
As Skipper – Sail Canada Intermediate CruisingVHF-ROC(M), ICC (for Greece & Croatia), previous skipper experience

Please contact us at 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



*Terms and Conditions

Flotilla costs explained

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