Flotilla Getaway

We’ve been hosting flotilla adventures around the world for over 20 years!

Flotilla Sailing

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.

Recently, Advantage Boating has spent:

    • 5 weeks in the Windward Islands with 40 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

Join us for our next flotilla in Greece September 12 – 26, 2020

Free Greece information session Tuesday January 21, 2020 @ 7 PM at the Britannia Yacht Club
RSVP HERE to attend

Sailing Greece

Upcoming Flotilla Trips:

  1. Greece – September 12-26, 2020 (Brochure)
    Free information session Jan 21, 2020 RSVP here to attend
  2. Leeward Islands & BVIs – February 2021
  3. Croatia – September 2021

Your flotilla leaders

What makes our trips different:

  • We have more than 20 years experience leading flotilla vacations around the world
  • Worry free sailing experience
  • Our experienced flotilla leaders plan the trip, organize the details, guide you from one beautiful anchorage to the next and travel along side the group throughout the sailing vacation
  • Each boat has a certified skipper and co-skipper on board
  • We charter newer boats ranging in size from 40-52′ (3-5 cabin)
  • Monohull and catamaran options are available
  • Mileage builder weeks are available for those who are looking for more of an instructional sailing experience including longer sailing stretches, more open water sailing and overnight sailing passages
  • Days are balanced to include f sailing, onshore exploring, socializing and relaxing

Our flotilla vacations sell out fast. 

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




FORMS:  2020 Down South 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

  • All prices are in US funds.
  • A deposit of 50% per person is required at the time of registration to secure your spot. The balance of the payment is due 75 days prior to departure.
  • Refund policy:  Full refund (less $500 UDS penalty) if more than 90 days prior to departure; 25% refund (of total trip cost) between 90 – 75 days prior to departure; NO REFUND if less than 75 days prior to departure.
  • Flotilla & Mileage Builder yacht charter costs explained

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 Jenneau boats are the regular boats used in this program, we reserve the right to substitute suitable yachts as necessary.  Catamaran options available.