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 Leeward Islands with 64 sailors in 2019.
  • 2 weeks in Croatia with 30 sailors in 2018
  • 4 weeks in the Antigua & Grenadines with 60 sailors in 2018

Some of our Caribbean sailing hotspots

Upcoming 2020 & 2021 Trips:  (brochure link)

1.  The Grenadines 12-day Flotilla, Feb 16 – 28, 2020 (St. Vincent &The Grenadines and Grenada)  Fee:  $1795*

2.  Martinique to Grenada Mileage Builder, Feb 8 – 15, 2020  Fee:  $1325*

3.  Grenada to Martinique Mileage Builder, Feb 29 – March 7, 2020  Fee:  $1325*

4.  September 2020:  Greece (more information available soon)

      5.  February 2021:  Leeward Islands (Sailing between Guadeloupe and Antigua)

      6.  September 2021:  Croatia


  • Mileage builder legs available for those looking for more of an instructional sailing experience, longer sailing stretches and more open water sailing.
  • Our boats range in size from 40 – 50′ (3-5 cabin) or similar type boat.
  • Monohull and Catamaran options available.


Our programs sell out fast.  Learn more by joining us for one of our free information sessions:

Grenadines flotilla playground


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 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.