Sailing San Diego Bay has never been this easy & fun.
Sometimes you just need to stop and take a breath. Relax with your friends and family and take in a side of San Diego you can only find on the water. Soak up the perfect SoCal sunshine, feel the breeze in the sails, and spot some of the area’s incredible marine wildlife on our sailing tours in San Diego.
More time on the water.
Our 3-hour Day and Sunset Sails offer more time on the water than any charter company in San Diego.
Everything is included.
Complimentary beer, soda, and snacks are included with every charter, so all you have to worry about is your SPF.
Safe, comfortable boats.
Our meticulously maintained fleet is helmed by US Coast Guard-certified captains.
“Whether you live in San Diego and want to get some fresh air and sail without a care, or you have visitors in town, which we did, you would be hard-pressed to find a better way to experience San Diego.”
– Paula, Google
Private San Diego Sailing Charters for Groups of 2-12
Make any of our San Diego sailing experiences an exclusive event for your friends and family. Whether you’re planning a romantic sail for two, celebrating a special occasion with family, enjoying a day out with friends, or giving back to your employees, our captained sailboat rentals in San Diego give you full access to the boat and the freedom to customize your journey.
Small Group Public Sailing Tours in San Diego
All of our public sails max out at 6 guests, so you’ll never be crowded in with a bunch of strangers when sailing the San Diego Harbor. Our tours offer a relaxed, enjoyable outing—ideal for individuals seeking a peaceful escape, couples looking to share a romantic experience, and small groups eager for an adventure. Enjoy the stunning views and sea breeze with plenty of space to unwind and truly savor the journey. Check out our most popular boat tours in San Diego!
No Rush. No Worries. No Experience Required.
The whole process of booking and checking in was simple with Sail San Diego. I loved riding with a small group of 6 people in total, it made for a really lovely experience. The captain made the sail fun and interactive. The three hour cruise time when by in a flash, and made me want to book again. I would strongly recommend Sail San Diego for its affordability, value, and expertise and friendliness of its staff.
– Lizz M. • Google
What a fabulous memory maker! Perfect activity reuniting family from St. Louis and Phoenix with us and our grandchildren. Beautiful sail, accommodating and knowledgeable captain, and spectacular sunset. Can’t wait for more visitors so we can do it again!
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Sailing San Diego Bay Since 1988.
We find that the people who make their way to San Diego, either to visit or to make their homes here, are seekers. They’re looking for that famous SoCal lifestyle: laid back, unpretentious, and fun. When you come out on the water with us, that’s exactly the vibe you’ll get.
As a locally-owned company with deep roots here, it’s our mission to show our guests the real San Diego from a perspective you can’t get anywhere else.
Can’t wait to see you on board our sailing tours of San Diego!
Cal & the Sail San Diego Team
Host Your Event On the Water
Whether you’re looking for a fun way to reward your team, or you want to throw the most memorable and fun party for your friends and family, the team at Sail San Diego will help you plan the perfect San Diego sailing experiences on board our pristine boats!