Sail San Diego is a boutique, family-run sailing company and one of San Diego's oldest operations. They pride themselves in their fleet of large, modern-day sailing yachts that they share with their guests. These yachts are the largest and roomiest sailing yachts for group, private, and intimate charters in San Diego, and are beautifully appointed, maintained, and meticulously cleaned before each cruise. The Captains and Crew at Sail San Diego work diligently to ensure their guests' outings are fun and exciting. With over 30 years of experience on the beautiful waters of San Diego Bay, they have the knowledge and expertise to make every visit unforgettable. Customers strongly recommend sailing with Sail San Diego, praising the top-tier vibes, bottomless beers and hard seltzers, and the captains' exceptional service and knowledge. The sailing experience is described as immaculate, with amazing snacks and a great atmosphere, making it a perfect choice for events like bachelor parties and team-building activities. Sail San Diego is a highly recommended way to enjoy the stunning scenery and wildlife of San Diego.
We sailed with Captain Dave and he was totally awesome. He was knowledgeable about the planes, aircraft carries, submarines that we saw. He spotted dolphins and sailed us close to them. I would sail with him again! Pleasant to talk to and could not have made the trip any better unless he could have controlled the sun.... read full comment
June 2025
Strongly recommend sailing with Sail San Diego. Our bachelor party booked a private sail with Captain Greg and the vibes were top tier. Not to mention the bottomless beers and hard seltzers. Amazing experience!
June 2025
Cannot rave enough about our experience with Sail San Diego! January greeted us with a huge smile and was extremely helpful and Captain Rhys was awesome! The sail boat was immaculately kept and the snacks were on point. 100% recommended!!! 🙌
