Skip to primary navigation Skip to content Skip to footer


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 Away | Sail Away! Morning Sail

We went on the morning sail and it was a perfect way to start the day. This great deal allowed all 3 of to have the most memorable 2 hours of our trip to San Diego. Wish we could’ve sailed all day! Our capt Greg was fun and knowledgeable and we had the time of our lives. Thanks for the memory Sail San Diego!

– Rachel, Tripadvisor
What a Wonderful Morning Morning Sail

What a wonderful group to work with. We had the perfect morning, saw so much wildlife, learned about the military in the area and saw beautiful sights. Our daughter was able to steer the sailboat for a while and learned about how the wind impacted the sails. If you go, use Sail San Diego. You wont be disappointed. Make sure you check out the membership opportunities.

– Judy, 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.