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    Shearwater Sailing

    5.0 (14 reviews)
    Closed 8:00 am - 9:00 pm

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    Silly A.

    We had a very fun day sailing with Kevin last Saturday and we did manage to see some whales. Kevin has lots of experience in sailing. Kevin and Jarod are cool and is just fun to go out sailing together and do some outdoor stuff at the ocean safely with experience tour guide. I enjoyed very much how the sail boat catches the wind and gets the full speed from 30 to 40 degree angle. Thanks ! Will definitely sail again with Kevin !

    Hilary M.

    We had planned a family trip to Monterey, our first vacation in years, and very last minute I decided we needed to do something SPECIAL and memorable. I'm talking, I decided to book a sunset sail around the bay the night before. Kevin at Shearwater was incredibly responsive and communicative during the booking process, and away we went! When I say it was unforgettable, I absolutely mean it. We had incredible weather that day, and the sunset was really breathtaking. The crew was equally as memorable. They made sure we were well taken care of, that the kids had a blast, and were an absolute pleasure to converse with. I can honestly say we'll be back again and again, every time we're in Monterey. Thank you SO MUCH Kevin and Sherry! We will absolutely recommend you to everyone visiting.

    View of the San Francisco skyline from Atalanta.
    Sofia S.

    I spent an incredible afternoon on Atalanta the most beautiful and well kept and extremely comfortable yacht have been! Captain Kevin is a very experienced sailor and knows how to provide a enjoyable sailing experience. If you are looking for a unforgettable sailing day look no further! Against all odds we even saw a whale in the SF bay!

    My husband booked us a 2 hour sunset cruise and this was by far one of the most beautiful experiences. The sail boat was clean, well maintained and made us feel comfortable from beginning to end. Kevin was able to take us right up to the whales that were out (a mama and a calf) and to watch the sea lions cluster for feeding, plus so much more. Thank you Kevin for making it all the more memorable with your excellent service, the knowledge you shared and passion for sailing. You and Chris took our experience to the next level. We both look forward to sailing with you again soon. Thank you for having us!

    That is me on the front of Captain Kevin's sailboat! How cool is that???!!!!

    Captain Kevin is a well seasoned sailing captain and will ensure every aspect of your trip is expertly addressed before, during and after your sail. A few notables for those who never sailed before: we sailed in the fall season and wore layers that consisted of hiking pants that are wind and water resistant as well as jackets with the same attributes. Underneath our clothing we wore light thermals and a layer of sporting shirts. Life at sea is unpredictable in terms of wildlife encounters, however, we were able to experience wildlife in a way that was almost surreal. Captain Kevin and his staff are not only knowledgeable of sailing, but they are versed in the wildlife you may encounter. For me and my sailing companions it was the trip of a lifetime! You will not regret sailing with Captain Kevin! My note to Captain Kevin: "Thank you to you and your crew for a job well done! We are thrilled that Shearwater Sailing was able to be a special part of our trip. You have the best combination of talent, skills and attitude that add up to memories of a lifetime! We would happily recommend Shearwater Sailing to future clients. May you be proud of the sail we had today and the difference you made to us. We are very grateful!

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    2 months ago

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    Kevin W.

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    2 years ago

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    3 years ago

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    Thank you Stephanie - was great to have you and your group on board!

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    Review Highlights - Shearwater Sailing

    Kevin at Shearwater was incredibly responsive and communicative during the booking process, and away we went!

    Mentioned in 14 reviews

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    Everything exceeded all expectations. Saw plenty of dolphins and whales, many very close to the…read moreboat. At $75 per person (times four) you wonder if it's going to be worth it. But when they deliver exactly what they promised, you walk away happy

    Shearwater Sailing - sailing - Updated August 2026

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