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

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The boats are put away for the winter after another fabulous summer of sailing, laughing and learning!  Thank you to all who took Mark and I sailing or rented a boat from us.  Memories of your avid willingness to share your smiles, stories and laughter will take us through the winter months.  When Spring comes we will be ready to do it again!

While there is more to life than speeding it up, and often people come to Orcas to slow down, our Trimaran sure is fun to sail fast!  So far she has exceeded 14 knots.  For comparison, the inter-island ferry can only reach 13kts!

    Our location, Lieber Haven Resort, in beautiful and sunny Obstruction Pass, allows us the unique choice of sailing in the protected waters of East Sound or jumping right into Rosario Strait.  Come see for yourself why our customers keep returning to sail with use, year after year. 

"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

   * 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!

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.



Note: (October 1st through April 30th) Please contact us via email for the upcoming season.

Ground Transportation

All 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