Sail San Diego - Sunset Cruises & Private Sailing Charters
The Best Experience in San Diego
The easy, laid-back, and totally unique way to see San Diego. Sailing since 1988.
Popular Sailing Experiences
$150 off Private Sails
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
$150 off Private Sails
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
"Our captain had me learning new things even as a long-time local! Beats the big tour attractions all day long! This is going to be a yearly trip for our group, for sure."
— Amy C.
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
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
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.
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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