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Take a break from the city and experience San Diego from the deck of a
pristine sailboat, helmed by a fun & experienced captain.



Family-Friendly, Certified Captains
Luxury Sailboats

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. Groups of 5+ save when booking as a private sail.

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. Perfect for individuals, couples, and small groups.

No Rush. No Worries. No Experience Required.

Great Way to Start the Day! Morning Sail

We did the morning tour and this was one of the best San Diego experiences we have done. From start to finish everything was easy. The sailboat was beautiful. Check in was quick and on time. Our group of four found the experience awesome. We live in San Diego and saw so many things we had never seen or even knew about. I'd definitely do this trip again.

– Cheryl D, Tripadvisor
Sail San Diego
Um..Love It!!! Day Sail

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
Sail San Diego
Family Sunset Sail! Sunset Sail

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!

– Judy M. • TripAdvisor

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


a person standing next to a body of water
a group of people in a boat on a body of water

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 unforgettable event on board our pristine sailboats!

Corporate Events | Bachelorette Parties | Birthday Parties

Visit the Sail San Diego Lounge

Stop by our retail and check-in lounge and say hi! We’ve got tons of limited edition sailing swag and cool brands like Helley Hansen, Sunski Sunglasses, and SunBum Sunscreen.