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Lessons and Boat Rental

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Boat rentals are available for a full day or half day.  In order to rent we ask that you have an intermediate level of boating experience.  We have 4 sailboats from 19 to 27 feet.

Prices vary based on boat.

Boat rentals are available for a full day or half day.  In order to rent we ask that you have a least an intermediate level of boating experience.  We have your choice of 3 sailboats, from 19 to 27 feet.

                Prices vary based on boat

Sailing lessons are private and personalized to you and your guests. They are available for a full day (6 to 7 hours) or half day (3 hours).  Rates include the boat, captain, and up to six passengers of your choosing.

half day rate..........................$575

full day rate...........................$1200



We began with a simple idea which continues to be our guide to business today:  Provide a fun sailing opportunity for visitors vacationing in the San Juan Islands.

Because we don't charge per person you will experience learning how to sail in the company of your traveling companions rather than with a group of strangers.  This way you get a private charter for you and yours only!  Every skippered charter is hands-on.  You will be sailing the boat and learning the ropes!

Where we are

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. Please call ahead as I am not often there.

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

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


"My husband arranged this sailing lesson for our recent visit to Orcas Island. This was the highlight of my trip. My husband has been sailing for a few years and I am brand new to the sport. Nat was awesome. He was so patient with my lack of knowledge and/or recall of the limited knowledge I have. The bay was quite choppy when we headed out but I immediately felt very confident with Nat at the helm. Nat is very personable and is a great teacher. I highly recommend Orcas Island sailing.'"

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