Caribbean Trips

Join us as we set sail on another exciting adventure in the Caribbean!

We will be traveling to St Martin, St Barts & Anguilla in January and February 2020. We have course boats available, and also fun boats for those that simply wish to vacation in paradise, whilst we do all the work. The dates are as follows:

  •  Intro and Intermediate Course Boat Jan. 25 – Feb. 1, 2020 (wk 1)
  •  Intermediate Course Boat Feb. 1 – Feb. 8, 2020 (wk 2)
  • Advanced Course Boat Feb. 8 – Feb. 15, 2020 (wk 3)
  • Intermediate Course Boat Feb. 15 – Feb. 22, 2020 (wk 4) (to be confirmed)

Whatever your experience, whatever your chosen destination, we can provide the sailing experience for you. We can be your gateway to a whole new world of on-water adventure. Whether you wish to improve your sailing skills or simply want a relaxing vacation, our professional staff is on hand to assist you.


Sailing from one paradise location to another makes for the best vacation experience. Whether you have your own group or want to join an party, we have options. We can arrange a bareboat charter or you can join in on a fun boat and sail in a flotilla.

Not only will you enjoy a winter sailing vacation, you’ll meet sailors from all around the world. The days are well planned out, with plenty of sailing and social activities. Sail your heart out during the day and then meet up with the rest of the group in an anchorage for an evening of festivities. You can also charter a boat of your own. Sail with our fleet and join the social gatherings we arrange.

World Destinations

We can arrange a sailing adventure anywhere in the world. Each route will take you on a journey through the famous and the little known treasures of each sailing area. We cater to every taste and ability; all you have to do is choose!

Our Caribbean program grows stronger each year because our professional instructors can provide customized sailing experiences for all levels of experience. Live aboard and earn your Sail Canada certification. Learning is easy when you are having fun!


Introduction to Caribbean Cruising

This is the “Fun Boat” and a great way to explore unfamiliar cruising grounds. Whether you’re a sailor or building your confidence for future bare boating, our introduction to Caribbean Cruising offers you the fun and adventure of exploring some of the world’s finest cruising areas, while providing you with an experienced team to guide you through unfamiliar waters. Our flotilla itineraries include special events like shore parties and snorkeling, and will give you the chance to mix with other sailors from around the world on a spacious catamaran.

Sail Canada Intermediate Cruising

Go ahead and dream of sailing in any exotic playground. This is the certification you need to charter a boat anywhere in the world. Sail Canada Intermediate Cruising course is the next logical step for sailors with their Basic Cruising Standard or prior sailing experience. A 7-day live-aboard course, it takes you step by step into the world of big boat sailing, including performing controlled sailing maneuvers, preparing meals aboard, and piloting the vessel into unfamiliar harbours or anchorages for an overnight stay.

Sail Canada Advanced Cruising

Are you ready to put all your sailing skills to the test? Then what better classroom than the Caribbean.

Meet the challenge of an overnight sail and improve upon your current sailing competencies and develop passage making skills, including round the clock sailing in a broad range of weather conditions. This course is designed to develop your technical and practical knowledge so that you can plan an extended passage, including navigation, standing watches, cooking a meal while underway and maintaining control of the boat in heavy weather.

How We Can Help

Whatever paradise you dream of, whatever anchorage you’re bound for, our professional staff are waiting to assist you. We can help choose a location, boat, provisions and much more. We have access to the world-wide fleets of all major charter companies. Let us put our knowledge to work for you so that your vacation is everything you dreamed of and much more. Simply call 416-203-3000 and ask to speak with Clive or Emma or email

Free Caribbean Info Nights 2020

Come down to the club for a presentation about this years destination. We will talk about itineraries, the boats, currency, food and any other questions you may have.

Stay tuned for 2020 Caribbean Info Night dates!

Please ask our staff for the newsletter detailing our next trip. Ask about our early bird booking specials!

A 25% deposit is all that is required to reserve your spot.