Fun Cat Sailing Adventures

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955 Harbor Island Dr
San Diego, CA 92101
Daily sailing adventures aboard 2 beautiful ocean going large sailing catamarans. Help sail, or just relax on an afternoon sailing adventure, or sunset sail. Our Captains are experienced and friendly, but our catamarans are really the stars of the show. My 1st catamaran "Tigress" is spacious, stable and comfortable for larger parties. My 2nd catamaran "Wind Drum" is the Ferrari of the sailing charters. Very fast, exciting and also comfortable. You can charter one of our catamarans privately, or join in, and pay per person. Small groups insure that our tours are fun and informal. After you come aboard, you will feel like a friend going for a sail with friends. We are very non commercial/touristy, and there are no phone #s or signs on our boats. We focus on quality, not quantity. We are of course Coast Guard licensed Captains with over 28 years experience taking San Diego guests out on the ocean. Catamarans are more fun.

Reviews

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5.0108 reviews
Marlee O.
8/25/2025

Such a great experience! We had captain Ryan and he was terrific. Super personable and went above and beyond without being obnoxious.

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Evan H.
9/5/2025

Fun Cat Sailing Adventures is hands down one of the best ways to experience San Diego from the water! Captain Ryan makes every outing feel special -- from provisioning the boat with beer, wine,...

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Whitney R.
9/10/2025

Kaia was an excellent captain, super personable and professional. She handled the boat with ease and made us laugh too! There was nine of us on the boat which was plenty roomy and comfortable....

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Lynne T.
7/27/2025

Captain Ryan is the best! It was a windy day and we got experience an awesome sailing experience while other captains took their clients around the bay with little motor instead of using sails!...

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Jason W.
6/27/2025

Exceptional experience. Beautiful sail out through the harbor and nearly out into open ocean. A mix of sail and motor. Sea lions, dolphins, epic Navy ships and submarines. Captain Matt was...

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United StatesCaliforniaSan DiegoFun Cat Sailing Adventures