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    Shearwater Sailing

    5.0 (14 reviews)
    Open 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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    4 years ago

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    5 years ago

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    4 years ago

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    3 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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    4 years ago

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    Ask the Community - Shearwater Sailing

    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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    Princess Monterey Whale Watching - Our boat

    Princess Monterey Whale Watching

    (443 reviews)

    A magical experience! Highly recommend. My family and I visited Monterey in June and we had to go…read morewhale watching when we found out it was whale season!! I picked Princess Monterey for several reasons. The most important one is that they offer 3 hour tours (shorter version) compared to 4 or more hour tours. Some of my family members get motion sickness, so I thought a shorter trip would be best. I also picked Princess Monterey because of their larger sized boats. It can get very bumpy out in the ocean, so having a larger boat helps with less motion sickness. We opted for a whale tour at 10am on a Saturday in late June. It was perfect and we got to see so many whales up close. The tour guides are very nice and knowledgeable during the ride. The boats are very spacious and have indoor and outdoor seating. I recommend you sit indoors when the boat takes off into the ocean. We all sat on the outer part of the boat and got super wet! Luckily it was a sunny day so our clothes were able to dry out. There's plenty of space, so sit inside until you get to the whale destination, then go out and enjoy the experience! If you tend to get motion sickness, you probably will during this trip. We had a very bumpy and windy ride, and at one point I felt a little queasy. There were some people who did get really sick during the trip, so don't forget your motion sickness medicine. I would also bring a warm coat as it gets cold once you're out in the ocean. It's also a great idea to bring sunblock and a hat. Unforgettable experience!

    Here's a fun and exciting review for your whale watching experience with Princess Monterey:…read more --- **Princess Monterey: A Whale of a Time (with a Splash of Adventure!)** Well, folks, if you're looking for a whale watching trip that's equal parts exhilarating and stomach-churning, look no further than Princess Monterey! Our group of 40 brave souls set sail yesterday, and let me tell you, it was a wild ride! Picture this: the ocean was a bit like a roller coaster--waves crashing, boats rocking, and our group members discovering just how quickly they could become best friends with the sea. Quite a few of us found ourselves feeling a bit queasy, but hey, who knew that whale watching came with a side of "hold on to your lunch"? But here's the kicker: despite the rough waters, we saw more whales than I've ever seen on any whale watching excursion! It was like a scene out of a nature documentary--humpbacks breaching, flukes flipping, and us squealing with delight (and maybe a little nausea). Every wave brought a new adventure, and the sight of those magnificent creatures made it all worth it! The crew was absolutely fantastic! They were like walking encyclopedias of the ocean, ready to answer every question we threw at them, no matter how ridiculous. "Is that a whale or just a really enthusiastic dolphin?"--they handled it all with grace and humor. Their enthusiasm was contagious, making even the toughest waves feel like a minor inconvenience. So, if you're up for a thrilling adventure with the chance to see some magnificent whales (and maybe test your sea legs), Princess Monterey is your go-to! Just bring some ginger ale for the ride trust me on that one!

    Shearwater Sailing - sailing - Updated September 2026

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