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 and cruise ‘n learn trips 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 sail 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.

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. 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 below at how we can help fill your sailing bucket list…

cruise ‘n learn weeks

Grenada to St. Lucia

February 2-9, 2020

St.Lucia to Antigua

February 9-16, 2020


International Yacht Racing

Caribbean 600 Offshore Race

February 22-28, 2020

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St.Maarten Heineken Regatta

March 3-8, 2020

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