5 Day Sailing Adventure in the Gulf Islands


Our 5 day sailing adventures begin and end at:

  • Sidney (10 minutes taxi from Victoria Airport)
  • Ladysmith (10 minute taxi from Nanaimo Airport)
  • Genoa Bay (10 minutes taxi from Maple Bay Airport)

They are customized marine adventures with an onboard wildlife naturalist and sailing instructor.

Two Whales Breeching

You’ll experience the cruising lifestyle, learn about the wildlife you’ll see, and improve your sailing capability by taking an CRYA certified course all at the same time!


Included in this adventure is:

  • 5 days / 4 nights sailing aboard 32 ft racing/cruiser
  • Onboard accommodation
  • Onboard meals
  • Customized Itinerary
  • CRYA Sailing Instruction Manuals & Log Books
  • Training Material
  • CRYA Course Certification
  • Licensed captain & instructor

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Helmsman Cruise and Learn is a Transport Canada Approved Recreational Boating School and participates in Transport Canada’s boat standards program called the Small Vessel Compliance Program.

Having a safe trip with a happy crew is always our primary objective.

Our Captain, Wade Karmann, has been actively sailing in the Gulf Islands for over 20 years, sailing single-handed as well as leading many sailing tours.   His local knowledge of both the water and the surrounding communities means that he can match each adventure with the unique interests of his guests.

Wade is certified by:

  • Canadian Recreational Yachting Association as an “Sailing Instructor”
  • Canadian Yachting Association as an “Advanced Skipper”
  • Transport Canada as a “Small Vessel Operator”

Wade is also a certified “Wildlife Naturalist” able to provide an integrated interpretation of the behaviour of and the issues being faced by the large variety of wildlife you’ll see in the area.  The result is a deeper experience for all on board.

Cruising on a sailboat is one of the most engaging ways to visit the Gulf Islands.  The scenery and wildlife that you’ll see is unparalleled.

Combine this with learning a new skill and experiencing the cruising lifestyle in one of the best sailing waters in the world and your vacation can be transformational.

  • Experience the live aboard cruising life style
  • View wildlife in their natural habitat
  • Visit many of the Gulf Island’s best attractions
  • Learn to Sail


Make a Reservation

Testimonials From Previous Guests


Cheri and Gary James

5 out of 5 stars!

I would highly recommend Captain Wade if you want to experience a truly amazing sailing experience. He planned a perfect 10 day adventure for a group of eight of us touring the beautiful Gulf islands. We had a great balance of sailing instruction and site seeing. His wealth of knowledge for sailing and the Gulg Island area made it a perfect vacation. We are happily letting our friends know what a great holiday we had. Thank you again. Congratulations to “Helmsman Cruise and Learn” for providing friendly and quality charter service.

Every success,

Cheri and Gary James

Greg Rosko

I had the pleasure of sailing with Wade on two occasions through the Gulf Islands and he is a very capable captain who makes everyone on board have a great time due to his good humour and skill of sailing. My wife is very afraid of water but Wade made her feel at home on the “Allegro” where we enjoyed a wonderful day of sailing and site seeing. Wade is a professional on the water and drives himself to be the best where every detail is looked after and everyone enjoys the time spent with him, I would highly recommend Wade on your sailing adventure.

Russ Glaser

I have had the pleasure of taking a guided cruise with Wade. We traveled through the gulf Islands and I had a magnificent time. We came to call Wade “the sail whisperer” because of his incredible sailing skills.  Can’t wait to sail again! I highly recommend Wade and his beautiful sailing vessel.

Commodore Mike Kosten

I first met Wade on a Caribbean sailing adventure, and he’s one of those gentlemen sailors with a friendly character, good humour, and great depth of sailing knowledge.  On that occasion, I was skipper and Wade was crew. Wade proved to be capable, eager, and easy-going (a nautical triple-crown).

We got along so well on that trip that Wade invited the captain and crew aboard his sailboat ‘Allegro’ a few months later.  We all enjoyed a jolly cruise of the Lower Gulf Islands with Wade as our skipper. His enjoyment of sailing is well matched by his competence, which comes from plenty of formal training, time spent on the water, and  reading to keep aware of current boating news.

I heartily recommend sailing with Wade. You’ll certainly learn from a capable fellow, and you’ll enjoy the trip!

Mike Kosten
Ail Sail Commodore

Dave Dunn

I’ve sailed with Wade on a number of occasions, from light air to strong breezes.  Wade closely observes the wind and sea conditions and plans a route that combines the most exciting sailing with safety and a timely arrival at the pub.  He is a natural teacher, explaining not just how to sail, but the details of why each procedure is best.  I am impressed by his knowledge and experience.  Great guy!

Jim Lee

I have sailed with Wade on several occasions as his crew as well as on my boat for Wednesday evening races. His sailing experience is extensive and I usually gained some knowledge that made me a better sailor. Wade is a safe sailor and explains all procedures very well.

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