San Francisco, California

Private Sail on the Bay

with Bob C.

7 reviews

Bob C.

You'll see San Francisco Bay from a unique perspective very few people get to experience

You’re on a boat! Hop aboard the Bolgeskrekk (we don’t know how to pronounce it either) for a leisurely sail around the bay. Captain Bob will take control of his vessel as you sip on wine and listen to your favorite music and admire the fact that you are actually sailing. Or, if you’re more the pirate type, Captain Bob will relinquish his duties to let you navigate the waters. No parrots on deck, please.

From secret coves to just a trip around San Francisco, this is a customizable trip designed to meet your sailing needs.

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up to 6 people
for 3 hours

Contact Bob
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Bob C.

Hello! I have over 35 years sailing experience on both the Chesapeake Bay and the SF Bay. I have 28 years experience sailing San Francisco Bay and its coast. Over the years, I have taken many people sailing on San Francisco Bay. I enjoy every sailing trip and make sure that my sailing guests have a great time as well. I enjoy the whole sailing experience, the water, wind, marine life, and most of all, sharing my experiences with others. I am married with three kids and have shared many enjoyable trips on the Bay watching them learn and grow fond of what makes sailing and the Bay great! They keep coming back for more! I hope that you will come sailing with me and enjoy the thrill and beauty of sailing on San Francisco Bay. I hold a US Coast Guard Captains license (OUPV). I am also licensed as a USCG Master Mariner with both a USCG commercial Sailing Endorsement and a commercial Towing Endorsement. Also, I hold a Transportation Worker Identification Credential (TWIC) too. Full profile

7 Reviews

Sarah J.

Sailing with Captain Bob was, by far, the highlight of our trip to San Francisco! If there is anyway to see the city it is definitely by sailboat. Not only did Captain Bob put us at ease, being two people completely unfamiliar with sailing, but he was very informative about everything we saw. Bonus when you get to see Dolphins and Sea Lions! It was the greatest experience to go from sailing so fast through the bay to relaxing and seeing the sites at the end and you also get to hang out Titantic style at the front of the boat, excellent picture taking time! But you definitely can get a good thrill while going at a good clip through the bay. It's so worth every single minute and I would do it again every week if I could! Capt'n Bob gives you such a personal experience while you're out there that you really feel like you're getting the first class treatment. You're not piled into a boat with a bunch of other people, it's like hanging out with a good friend on his boat for the day. It was the neatest thing to see my boyfriend steering a sailboat for the last half of the trip! Captain Bob knows what he is doing and I will definitely be telling everyone I know to check him out when they go to San Francisco next!

Felipe H.

Was a great experience sailing around the bay. Captain Bob is friendly, knowledgeable and takes you to sail around this wonderful bay. What else would you want? Already recommending him to friends!

June L.

Captain Bob's sailing tour departed from Treasure Island, where we checked out the industrial shipping ports as well as the construction of the new Bay Bridge. Having come from a family of sailors and being at sea since he was in diapers, Bob is super knowledgeable about sailing. You should ask him about the origin of his boat's name! He's pretty flexible, really nice, will take you wherever you want to go, and also show you really cool spots if you're unsure. All your nautical curiosities and questions will be answered.

Victoria S.

As a birthday gift for my husband, we enjoyed a great afternoon of sailing with Captain Bob on the Bay! The sail gave us a wonderful and close personal view of the SF skylight, Pac Bell Park and McCovey Cove. We enjoyed the beer and wine that Captain Bob provided, and found him to be very knowledgable and informative about the various boats on the bay and sights to see! Great trip!

Lynn T.

This was my first time ever on a sailing boat, and we couldn't have asked for a better captain than Captain Bob. The entire trip was amazing - the view was breathtaking, our vessel was sturdy, everything went above and beyond my wildest expectations. I've lived in the Bay Area for over 7 years, and have never before been able to see this city from such an extraordinary vantage point. I would highly highly recommend this experience to anyone who want to experience an unique experience they will not forget anytime soon.

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