Orcas Island Sailing

Olga, United States

5

Closed now

18 reviews

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Telephone:
+1 360-310-0100
Website:
www.orcassailing.com
Address:
1945 Obstruction Pass Rd, Olga, WA, 98279
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Bussiness info

Good for Kids
Yes

Today

Today 9:00 am – 6:00 pm
Closed now
Local time (Olga) 02:56 Friday, 30 May 2025

Business hours

Monday 9:00 am – 6:00 pm
Tuesday 9:00 am – 6:00 pm
Wednesday 9:00 am – 6:00 pm
Thursday 9:00 am – 6:00 pm
Friday 9:00 am – 6:00 pm
Saturday 9:00 am – 6:00 pm
Sunday 9:00 am – 6:00 pm

Description

Specialties

We offer personalized sailing lessons in a calm, nurturing environment where having fun is emphasized! No prior experience required. You will be sailing the boat :-) We charge for the boat and instructor rather than per person. This ensures that only you and yours are sharing the thrill of learning to sail. We can accommodate from 1 to 6 passengers depending on the boat.

For experienced sailors we offer a nice selection of small day sailors and a small cruising sloop for rent. Choose from a half day or multiple days to explore the San Juan Islands at your own pace.

History

Established in 2001.

Orcas Island Sailing began with a dream to teach sailing to families and couples vacationing on Orcas Island. One 28′ sloop quickly led to a small fleet, originally located at Rosario resort. We are now located on the South-​East corner of Orcas in Obstruction Pass, at Lieber Haven Resort. Our new location allows for sailing in the protected waters of East Sound or Rosario Strait. Our fleet of boats has distilled to small daysailers and a small cruiser for overnight bareboat charters. We charge for the boat and captain rather than per person. This insures that only you and those you choose to take along are part of the trip. We love this and so do our customers. It has given us the opportunity to get to know our customers on a personal level, many of whom we now call friends, many who come back year after year. We are a small business and intend to stay that way, to keep the stress levels low and to maximize the fun!

Meet the Business Owner

Ben B.

Business Owner

I grew up sailing in the early 70’s on Lake Pend Oreille in Northern Idaho. At the age of 14 I was solo sailing the family 22′ sloop more often than not. Prior to starting Orcas Island Sailing I was a middle school science teacher for 6 years. Today I enjoy letting others take me sailing while I teach them just exactly what makes a sailboat «go». I love to see the ah ha moments that invariably happen! I’ve found that putting families or couples at the helm and controlling the sails while I offer calm encouragement is the best way for everyone to have a great time and learn how to sail.

Nearby

Near this location:
1
mi
Spring Bay Cabin
464 Springbay Trail
1
mi
Orcas Island Bayside cottages
65 Willis Ln
1
mi
Spring Bay Kayak Tours
464 Springbay Trl
1
mi
Furniture Revived
236 Woodside Farm Rd
1
mi
M Sawyer Drilling & Pump
621 Obstruction Pass Rd
1.2
mi
Buck Bay Shellfish Farm
77 EJ Young Rd

18 reviews of Orcas Island Sailing

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Place rating: 5
San Jose, CA
While we were sad to learn that Ben, the previous owner of Orcas Sailing, had moved on, we decided to to go out today with Nat, the new owner. Not an iota of quality has been lost in the transition., Nat asked us what kind of experience we wanted (we said we wanted to learn to sail), listened, and we got to basically sail the boat ourselves under his patient tutelage.
Nat is knowledgeable and charming and cool as a cucumber — necessary when learning to navigate a boat full of family!
Plus he is open to stopping on Blakely for ice cream on the way back.
Such a great time! Thank you Nat. Once again, Orcas Sailing was the highlight of our week here.
Place rating: 5
Redmond, WA
When I read the reviews before our trip, I wondered if all these people could actually be Ben’s friends:-) But I just met him on our trip (my husband, 14 yo son, his 2 friends and me) and I totally agree. He has a lovely, calm manner but really knows what he’s talking about. He gently (but persistently) takes passengers through everything from the process of rigging the boat to sailing in different conditions and finally docking. I’ve sailed before with others who tried to teach me but this time I actually remember – and had a great time in the process. He loved getting into the science of it but was also just a pleasant guide. We saw harbor porpoises and flying fish and the three 14 yos were in charge of the rudder the whole time, and they did a fine job under Ben’s guidance.
Place rating: 5
Oakland, CA
My husband and I had to decide whether or not to keep our lesson on a blustery day. Ben carefully and frankly laid out the considerations, including the probability of spending a lot of time tilted over in a way that might be unnerving. After our conversation, I felt completely confident about going out as a first time sailor with Ben as our coach and instructor. We are so glad we did — our time sailing with Ben became the highlight of our weeklong vacation on Orcas Island. Ben is a kind, honest and friendly person. As a lifelong educator, I give him my highest compliment — he is a very skilled teacher. We had a wonderful experience!
Place rating: 5
Seattle, WA
Oh what fun! Ben is an amazing teacher. We learned so much while having a blast. The boat was clean and well maintained. We will definitely see Ben again.
Place rating: 5
Portland, OR
We can’t say enough good things about our experience today with Ben and Orcas Island Sailing. It was my wife and myself, plus my 16 y/​o daughter and my 13 y/​o son. Ben is a fantastic teacher and able to talk in a way to make sailing fun and accessible to any age and experience level. We went out in the 19′ Pearson Resolute which was the perfect boat for our family. It was a 10 plus!!!
Place rating: 5
Vancouver, WA
Ben was amazing! He was educated, skilled, friendly, and fun.
I’m a curious guy and ask a lot of questions; Ben had answers for all of them somehow. He clearly knows his stuff about sailing and its physics and history, and his educational background shows clearly in the concise and cogent way that he explains these things.
Neither my wife or I had any complaints and would heartily recommend Orcas Island Sailing to anybody with an interest.
If you have the chance, take the trimaran — it’s fast! We got up to 13.1kt in it in mild winds and it was our first time out. That’s about twice as fast as the top speed of his monohull boats.
Place rating: 5
Sacramento, CA
Simply put: Ben is fantastic! He welcomed us, a couple with little sailing experience, with such genuine warmth, enthusiasm, and curiosity, that we immediately felt at ease. We then preceded to enjoy the heck out of our introductory sailing lesson. For hours Ben educated us on the physics and «touchy feely» aspects of sailing, tailoring his explanations to our divergent learning styles. He truly loves sailing, teaching, and. people! You will be so happy you choose to spend time learning with him.
Place rating: 5
Saint Louis, MO
Ben is amazing! My experience sailing with Orcas Island Sailing far exceeded my expectations. If you have ever wanted to learn to sail I would highly recommend Captain Ben. He provided the perfect combination of lesson and fun during my trip with him! Thanks Ben… can’t wait to do it again!
Place rating: 5
Chicago, IL
Ben runs a great sailing shop and is a fantastic instructor. He was able to accomodate our unique schedule for a day trip and took an avid interest in our desire to learn more about sailing. It was a great day on the water!
Place rating: 5
Provo, UT
It would be hard to imagine a better way for a family to enjoy a vacation in the San Juan Islands. You get to learn to sail, and actually sail the boat, taught by a very nice teacher.
Place rating: 5
Longmont, CO
Everything above has been said. Our family of 4 enjoyed our time out immensely. We didn’t get to go far as it was a high wind day, but Ben got us eat safe place and we sailed and sailed. Great family activity!
Place rating: 5
Seattle, WA
i rented Jazz (Rhodes 19′ keelboat) back in August. my wife and i headed to orcas from seattle for a wedding one weekend and spur of the moment googled some sailing opportunities on the drive up to the ferry. i’ve been sailing all my life and i was shocked to find a way to rent small sailboats for a half day for a reasonable price, and at the last minute!
ben, naturally, wanted to talk to me about my sailing experience, gave me a quick run down of the rules (all normal ones), and then watched me rig it to be sure i was who i said i was. the boat was amazing — in top shape, METICULOUSLY stowed and completely clean. if you’re a real sailor then there is nothing you value more than a meticulous stow job so you can see/​find everything you need when you need it. the engine was full of gas and we motored out into the harbor to raise the sails. everything was smooth and and boat really sliced through the waves and current in 15kts! (edit: the engine also started smoothly every time!)
ben is super nice and helpful and if you don’t know how to sail, offers lessons (if i’m remembering correctly). whether you are an experienced sailor or a landlubber wanting to learn, check out orcas island sailing’s website.
happy sailing!
Place rating: 5
Tacoma, WA
Ben was great! He was educational and fun, we really felt like we were spending the day on the water with a good friend!
Place rating: 5
Washington, DC
Ben lent us one of his prize fleet for the afternoon and our group had an amazing time. One of use dropped a camera in the water and Ben offered to fish it out with his scuba gear! Ben had set up a time to meet with our captain, who had sailing experience but missed the initial meeting, and called back so we did in fact get the little test in and got to go out on the water.
Place rating: 5
Chicago, IL
My friends and I had such a great time sailing thanks to Captain Ben. It is clear that Ben is passionate about sailing and he is an incredible instructor. He kept us all engaged by teaching us how to sail and by pushing our understanding of the physics behind sailing. He was informative, friendly and encouraging every step of the way. Living in Chicago, I would make the trip back to Orcas Island Sailing to learn more from Ben. If you have the opportunity, I highly recommend this trip!
Place rating: 5
Olga, WA
My children and myself all learned how to sail with Orcas Island Sailing. Being in the San Islands is one of the most amazing experiences in the world and I can’t think of a better way to experience them than from a sailboat.
Place rating: 5
Byron, CA
My sister, brother-​in-​law, and I spent an afternoon sailing with Captain Ben of Orcas Island Sailing and had a terrific time. Captain Ben is clearly passionate about sailing, and a patient teacher. When he discovered my brother-in-law’s interest in the science of sailing his enthusiasm was palpable. It was hands on learning as soon as we boarded the boat, but no pressure on my sister who wanted to relax and be a passenger. Captain Ben encouraged us to explore our own limits while making us confident in our safety. I would wholeheartedly recommend Captain Ben and Orcas Island Sailing.
Place rating: 5
Seattle, WA
We had such a great experience with Orcas Island Sailing that we chartered boats two weekends in a row. The first weekend, we did a day sail, cruising up Eastsound for the afternoon. This past weekend, we chartered Pilgrim, a 26 ft Pearson for two nights — it was awesome. The boats are perfectly maintained and come with everything you need, and Ben is a wealth of local and sailing knowlege. At the mouth of East Sound, you are centrally located and can easily explore Orcas, Lopez, Shaw and San Juan Islands. Highly recommend a trip!