Nat took my family out last month for an amazing half day on the water. It was truly the highlight of our month on Orcas! He has gorgeous boats but most importantly, is a very skilled sailor and guide and just such a kind human. We plan to do another sailing with Nat when we're next back on Orcas and I cannot recommend the experience highly enough! read more

We had an amazing lesson and a wonderful time with Orcas Island Sailing. Nat was so kind and patient in his learning style and also loads of fun. Highly recommend. We made our way over towards Blakely from the dock at Leiberhaven. Great teacher, great tkme read more

Captain Nat is a very competent and friendly skipper! He is extremely knowledgeable about the tides and currents around the San Juan islands and is happy to teach as much as you'd like to know about sailing in the area. My group included some experienced sailors and captain Nat let us maximize our time on his well maintained Catalina 27 to practice exhilarating maneuvers including sailing through narrow passes, docking on sail only, and generally improving our skills. He's very thoughtful and notices how all members of the group are doing. Definitely the highlight of my visit to Orcas. read more

Orcas Island Sailing - The stern of a 27' boat with 5 people, sailing through peavine pass on a clear day. - Sailing Near Me - Olga, Washington

Our group of six had a terrific 3-hour tour with Captain Nat. He mixed just the right amount of instruction while allowing us the room to learn the basics. Easygoing and completely in control, we felt very safe and loved the cruise. read more

Such an amazing day on the water. My father and I took a sailing lesson from Nat while my 4 sisters enjoyed just being on the water. I learned more from Nat in the 4 hours than I did in almost a week of classes elsewhere. He was knowledgeable in sailing and in the area and history. Excited to go back with my husband for some more instruction and fun on the water! read more

Orcas Island Sailing - Sailing Near Me - Olga, Washington

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Captian Nat is where it's at! We had such an amazing family day sailing with Nat around beautiful Orcas Island. He was extremely patient, great with our kiddos, and made us feel as though we were natural sailors. If you are thinking, even in the slightest, about going out for a sail, just do it! Do it now or forever regret missing out on an amazing experience. We can't wait to sail with Nat again next year! read more

Go! Do this! Nat is so knowledgeable, so kind, so competent. We had a great time with him. He asked immediately about our hopes and dreams for our outing, and about our fears . He was sensitive to each of them and tailored our sail carefully to match them. We loved being with him and we will definitely do this again next time we are back. read more

Our family of 5 so very much enjoyed our time. Captain Nat was so helpful in our planning and in asking what we wanted. We wanted to learn how to sail and that was exactly what we did. He was patient and helpful and we learned so much. Everyone took turns trying all the different jobs on the boat and we all (two adults and kids ages 17, 14, and 11) were thrilled with our day. Thank you, Captain Nat! read more

Orcas Island Sailing - Sailing Near Me - Olga, Washington

We had such a good time sailing with Captain Nat that we did it again the next day :) We had a fantastic couple days of sailing around Orcas, stopping at Blakely island for a picnic on the second day. Nat was fantastic with my 10yo daughter, who is on the Autism spectrum, chatting with her for a good part of each ride and giving her tasks she enjoyed - I'd worried whether she'd be able to focus through 2 days of sailing, but with Nat she had a great time! We'll definitely be back. read more

We had an amazing experience with Nat on his Catalina 27. Taking the challenge to not use the motor, but truly sail in and out the harbor, made it the experience we were looking for: pure sailing. Being a family of 4, Nat was totally comfortable having our kids steer, do the sails etc. and Nat a pleasant way of teaching them and us while just being a lot of fun as well (great stories). We loved every minute of it! read more

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Truly amazing. This was easily the highlight of our trip to Orcas Island. Although we didn't have a ton of wind on our sailing day, Nat made it well worth it with great conversation and teaching us everything he could! I can't recommend this experience enough, Orcas island is absolutely beautiful and if you are at all 'on the fence' about doing this, DO IT! you won't regret it, Nat is an incredible host and makes you feel welcome. He is open to doing anything you want, sailing over to Blakely Island for ice cream, food, and drinks was his recommendation and it was absolutely perfect. Best experience I've ever had, 10000000 times recommend. Will definitely be back for round 2! read more

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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. read more

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. read more

We had an amazing time with Nat this week. He's a fun, friendly captain and a patient teacher. He knew all the good spots to see wildlife, check out incredible homes or grab a beer in islands with private boat access only. He made the whole trip very fun and we'll definitely be going again! THANKS NAT! read more

I had a fantastic experience with Orcas Island Sailing. I rented a 27' sloop and Nat was extremely helpful in arranging our arrival, offering ideas on where to set sail to, setting up the boat and ensuring we had a fantastic experience. Really friendly and great place to sail from! read more

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!!! read more

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This was the highlight of our Orcas Island trip. We signed up for the three hour lesson with Nat. He is a really fun person and a great instructor, he allowed us to sail the entire time. He taught technique while explaining the fundamentals in a way that we could understand easily. We had a perfect day on the water and stopped at Blakely Island for coffee on the way back. We hope to schedule another trip or lesson in future with Nat, I would recommend Orcas Island Sailing to all of my friends. read more

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. read more

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! read more

Nat was very friendly and helpful. He gave us good ideas on where to sail and covered the basics of tides/currents. Our family of 3 had a great time and I'd definitely go again. We did a half day rental but I think Nat would be a great instructor, he's friendly and calm. read more

Ben was great! He was educational and fun, we really felt like we were spending the day on the water with a good friend!

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. read more

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! read more

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. read more

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. read more

We had a great time on our 1/2 day sailing adventure. Nat was very warm and welcoming, and so sweet with our two young kids. The boat was well maintained, ready to go when we arrived and just what we were looking for. Highly recommend! read more

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! read more

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! read more

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. read more

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! read more

We recently completed our first sailing lesson with Nat from Orcas Island Sailing. Whether you are new to sailing or looking for more advanced instruction, look no further! Nat was calm and patient, working within our comfort level to give us a day of hands-on sailing experience in the calm and beautiful waters of Orcas Island. Given his extensive background on a variety of boats, Nat is able to "go deep" on the mechanics of sailing or simply offer engaging stories of his adventures at sea. Above all, Nat's excellent and patient demeanor truly set him apart. We highly recommend Orcas Island Sailing! read more

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. read more

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! read more

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! read more

Just went sailing with Ben for the second time, every bit as much fun as the first. The wind was a little different from last year, so we tacked up Eastsound & got to see The Rosario Resort from the water. 4+ hours, a fantastic afternoon. Ben is a great instructor and a great companion. He will teach you as much as you want to know, or just let you enjoy the time on the water, whatever you want. We were a party of four, two interested in learning sailing, two not so interested. Everyone had a fine time. We're going to make this an annual event. read more

Ben runs an excellent operation at Orcas Island Sailing. He is extremely personable and accommodating to your group's sailing needs. We took out 2 different boats over 3 days and have fun trying each boat over the week. The location is great because it gives you easy access to East Sound, which has amazing views and little boat traffic compared to other harbors on the island. read more

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. read more

Took the whole family sailing with Nat and had amazing time. Nat didn't flinch when we said we had a 14 month old ands a five year old with a penchant for sea sickness. He was totally flexible in meeting our needs and an amazing teacher to boot. We had a relaxed fun time and I learned a whole lot about how to sail. Like any good teacher, he met me, his student, where I was at; with just enough knowledge about sailing to be dangerous. He humored my non stop questioning, took great care of our kids, and ensured that we had an awesome experience. I ended up sailing the boat, with Nat and our son tacking the jib as we tacked, we practiced heaving to, points of sail, trimming the sails and catching the wind, and all the while had a great time cruising around. The next time we're back we'll definitely be getting in touch with Nat, hopefully to charter a boat of our own and go sailing in the San Juans. read more

I recently had the pleasure of sailing with Nat and my two teenagers on our recent trip to Orcas Island. Very little excites and captivates my daughter like sailing. Nat's natural teaching ability and relaxed style expanded my daughter's interests even further and helped create an unforgettable experience for all of us. Orcas Island Sailing's uncommon approach to creating a hands-on experience enlivens the typical sailing tour, allowing sailors of different skill levels to understand sailing's natural principles and own the feeling of capturing the wind. I highly recommend a sail with Nat and Orcas Island Sailing. It will become a cherished memory. read more