The Best Sailing Experience in San Diego

The easy, laid-back, and totally unique way to see San Diego. Sailing since 1988.

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Sail Your Way

Choose ticketed or private sails. It’s “you time” either way.

Everything is Included

Beer, soda, and snacks - all included. Just bring your SPF.

Your Own Local Captain

US Coast Guard certified, fun, and always up for a great day.

Two Ways to Sail. Same Incredible Views.

Choose a ticketed sail for individuals or small groups, or go private for up to 10 guests (best for groups of 4+).

a group of kids on a boat

Great for families!

Morning Sails

Calm waters, mild wind, two hours. Perfect for families with kiddos. And you might even spot some wildlife!

Starting at $89

  • 2 hours
  • 6-10 guests
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a sailboat on the water

Local favorite!

Midday Sails

The wind is up, the boat's moving, and the water's looking real good. This is San Diego sailing at its peak.

Starting at $109

  • 3 hours
  • 6-10 guests
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a sailboat on the water

The perfect date night!

Sunset Sails

End your day right: on the water with your favorite people, drink in hand, under San Diego’s famous cotton-candy skies.

Starting at $119

  • 3 hours
  • 6-10 guests
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Perfect getaway!

Private All-Day Sails

With six hours on the water, you’ve got time to do it all – sail the coast, catch the wildlife, drop anchor and take a swim.

Starting at $750

  • 6 hours
  • Up to 10 guests
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Your Boat. Your People. Your Perfect Day on the Water.

No crowds. No stress. Just your group, your own sailboat, and San Diego as it's meant to be seen.

Corporate Outings

For groups from as few as 2 guests to over 100.

Ditch the office or conference center and take your team sailing! Perfect for entertaining clients, teambuilding, or just kicking back with your crew.

Racing Regattas • VIP Executive Sails • Team Incentive Outings

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Large Group Sails

For groups up to 22 guests.

Your sail, your way. Cast off with the people who matter most on a spacious, premium sailboat – on your schedule. We'll even bring the drinks.

Anchor & Swim • Rady Shell Concerts • Catering & Bar Pacakges Available

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a group of people on a boat giving each other a high five

Sailing San Diego Bay Since 1988.

People come to San Diego – whether for a visit or for a lifetime – because they're looking for something special. That laid-back, unpretentious, SoCal lifestyle. When you sail with us, that's exactly what you'll find.


As a locally-owned company with deep roots here, we love sharing the real San Diego – the one best seen from the water. With us, you're sailing with friends.

Cal & the Sail San Diego Team

Like Sailing with Friends.
If Your Friends Had an Awesome Boat.

Retail + Lounge

Mark the moment with limited-edition sailing swag from cool brands like Helly Hansen, Sunski, and more. Grab a cold drink, check in for your sail, and don’t forget the SunBum SPF.

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