making gorgeous places and epic races

more accessible to sailors and sailors-in-progress


Sea to Sky Sailing is offering individual berths for select overseas racing events each year.

We secure a yacht through our network of trusted private owners, organize all the details of the trip, and send one of our best skippers to race with you every step of the way. You show up and sail, becoming part of the kick-ass team we’ve formed for that event, making lifelong friendships and lasting memories (fair warning: only some of which you’ll be able to explain to other people).

Our skippers are highly trained instructors and experienced racers with a wide range of expertise, able to help you build your sailing skills every step of the way. Together with one of our first mates, they will make sure you come out the other side of this awesome experience smiling, in one piece, and a far better sailor than when you first stepped aboard.

Some events are beginner-friendly, others do require a fair level of experience for the safety of the crew and boat as a whole. If you need to up-skill before joining us, check out our 5-star training program based out of West Vancouver.

Take a gander at how we can help fill your sailing bucket list…

St.Maarten Heineken Regatta

February 28-March 3, 2019

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On board a J-120

The tagline of this almost criminally fun regatta is #seriousracing #seriousfun and they really, really mean it. Caribbean racing and hospitality and its very best!

Our 2019 team aboard J-Aguar was FULL. Check out our posts on Facebook or Instagram for a taste of what this awesome regatta involved & stay tuned for details on our 2020 return to the Heineken and the rest of the Caribbean season!


We’ll be adding more events as we finalize details with yacht owners. On our list for 2020:

Grenada Race Week: January 26-31, 2020

Caribbean 600: February 24-28, 2020

St.Maarten Heineken Regatta: March 5-8, 2020

Les Voiles de St.Barth’s: April 12-18, 2020


Follow us for updates & don’t get left behind!