Have you been dreaming about sailing in the San Juan Islands? 

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NOTE:  We are closing for the season September 22.  Limited availability between Labor Day and the 22nd.

My mother, myself and our six year old went sailing with Ben from Orcas Island Sailing.  The experience was amazing.  We had no experience in sailing and he was so patient with us - especially our six year old.  Best experience on the island by far ---thanks Ben!

Trip Advisor Review  

"Ben is a favorite with our children, our guests, and with us: we always learn from him, we always have fun."  Peter F.  Menlo Park, CA


Come see for yourself why our customers keep returning to sail with us, year after year. 



    * Family/couple oriented.  Each lesson is just you and yours, the boat and the captain, no crowds.

  * Fun oriented professional instructors (Ben, Tara and Mark) with a dedication to calmly teach you sailing!

*Read our reviews (or leave one) at Trip Advisor by clicking here and Yelp by clicking here.


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Reservations and Information

Orcas Island Sailing is a small business that intends to stay that way.  I answer the phone when I'm available and rely on you to leave a message when I'm out.  This business is staying small so I can provide the best service to my customers, keep my stress levels low, and have as much FUN as possible!  Myself (Ben), Mark and Tara are committed to providing the best sailing experience possible.  Don't look for us to grow any larger ;-))

I'm open nearly every day in the summer and you can usually reach me between 9 AM and 7 PM.  Sometimes sending a text message is the best way to reach me quickly.


Driving Directions

We are located at 1945 Obstruction Pass Rd, Olga, WA  98279

From Eastsound, drive south through Moran State Park.  At the Artworks building in Olga turn left onto Point Lawrence Rd.  Two intersections later veer right onto Obstruction Pass Rd.  At the end of this road is the county boat ramp and parking lot.  My office shack is adjacent to the boat ramp just inside the property of Lieber Haven Resort. 

From Doe Bay, turn left onto Obstruction Pass Rd then follow the directions above.

NOTE:  We are located at Lieber Haven Resort, in Obstruction Pass, at the end of the Obstruction Pass Rd.  We are not at Obstruction Pass State Park which is at the end of Trails Rd.

Ground Transportation

A-ll forms of ground transportation can be easily arranged by calling Orcas Island Shuttle and Rental Car.  We encourage you to walk on the ferry!  Click here to go directly to their website or call 360-376-7433 for info!


  In 2007 author and world renown lecturer James Bach told me he had a goal to learn to sail one of my boats by himself.  James was an outstanding student, always wanting me to push his comfort zone.  During one of his lessons he mentioned he was going to put me in his forthcoming book.  Well, here is the book!  Some of his experiences learning how to sail are captured in the Epilogue.  Click here to read an excerpt from the Epilogue!  ~  Ben