“Amazing” “Exceptional” “Outstanding”

Helmsman Cruise and Learn offers 3 and 5 day Sailing Adventures in the Gulf Islands.  


Join us for an unforgettable experience while you learn to crew or skipper a sea going yacht.

Sailings available every week between May 1 and  September 31!

About the Sailing

You’ll cruise to remote Gulf Island destinations, immerse yourself in breathtaking marine settings and learn to sail by taking CRYA certified sailing lessons at the same time!


Included in each multi-day sailing adventure is:


  • On-board accommodation
  • On-board meals
  • Customized itinerary
  • Sailing Instructor & Wildlife Naturalist
  • CRYA sailing instruction manuals & log books
  • CRYA course certification (Competent  Crew, Day Skipper, Coastal Navigation)


Sailings depart and return from Genoa Bay, Sidney or Ladysmith.

About the Adventure

Whether you’re interested in quiet anchorages, local markets, hiking, kayaking, wildlife viewing, bird watching or incredible seafood restaurants we’ve got it covered!


Adventure Checklist:

  • Sail as much as possible!
  • Witness marine wildlife in natural habitat 
  • Drop anchor at “boat only access“ marine park
  • Swim in the ocean... or not
  • Sleep on-board while at anchor 
  • Watch sunset from the cockpit 

Sailing Adventures

5 Day Sailing Adventure

Event Details

5 Day Sailing Adventure

$1375/person (based upon 3 person min)


Cruise the Gulf Islands on a sailboat with a wildlife naturalist and sailing Instructor. Experience th...

Event Details

3 Day Sailing Adventure

Event Details

3 Day Sailing Adventure

$825/person (based upon 3 person min)


Cruise the Gulf Islands on a sailboat with a wildlife naturalist and sailing Instructor. Experience the...

Event Details

3 Hour Sailing Adventure

Event Details

3 Hour Sailing Adventure

$75/person (based upon 2 person min)


This is a 3 hour sailing adventure across Cowichan Bay out into Sansum Narrows.  

Sailings depart daily ...

Event Details

Gift Certificates

Event Details

Gift Certificates

Sailing Adventures make fantastic gifts!


You prepay any portion of the fee for any of the sailing adventures.  We’ll send you a beautiful per...

Event Details

Reservations and Inquiries

SPECIAL REQUESTS AVAILABLE

We can customize an itinerary to emphasize your interests. If you have a special request, send us a message, and we will be sure to get back to you soon.

Message us on WhatsApp

Helmsman Cruise and Learn

(250) 510-6698