From The Docks – The Perfect Date Night Out

What could be more romantic than a date on your own private sailing yacht? Valentine’s day is right around the corner! Are you looking to plan something special, memorable & unique?

Minimal planning is necessary on your part; Sail San Diego has you covered – we’ve been doing this since 1988! Simply meet us down at the docks & we’ll have your yacht waiting for you to embark on a romantic 3-hour sail.

Join us for a day or sunset sail, whale watching, or you could even book a sailing lesson as a fun & adventurous date! You can join a public sail with others or book the yacht privately for just you & your plus one.

Not able to celebrate on Valentine’s Day? No problem! Gift your sweetheart a sailing experience to use at a later time. You can find Gift Cards on our website.

You’re more than welcome to bring your own food to enjoy while you sail if you pack a picnic & your own beverages (just no red wine or hard liquor). There are also several great restaurants within walking distance from our docks; you can make a reservation to follow your romantic sail with us! (Brigantine, Pomodoro, Pummaro, Miguel’s, Pizza Nova & more!)

We love hosting our guests for holidays & special occasions – lately, we’ve had the privilege of celebrating several wedding proposals aboard our yachts! Join us this Valentine’s Day with your boo boo honeybear. Blankets are back! Cuddle up with your snuggle bunny & a can of Juneshine hard kombucha for a romantic experience on the water that you’ll never forget!

All shown prices have NO EXTRA TAXES OR FEES

We do gently remind our guests to think of their Captain with Gratuity. They work hard to give you the best experience and the best sail every day.

Thank you very much for booking with Sail San Diego. Here are a couple of things to make your experience more memorable:

  • Please plan to arrive 30 minutes before the start of your sail.
  • Dress appropriately to the weather, and remember it is often a little chillier out on the open water than on land.
  • We always recommend wearing soft (non-black soles) shoes.
  • Arrive at 2720 Shelter Island Drive, San Diego Ca 92106.

Terms and Cancellation Policy

  • If you need to cancel or reschedule your sail within 3 days of your trip, you can do so on the website, inside of 3 days please call 1-619-297-7426.
  • Our boats will sail in light rain as well as other “safe weather”.
  • Reservations may be canceled for a full refund only if canceled within 3 days of your reservation.
  • For Private and Bareboat Charters, Sail San Diego will enforce a cleaning fee if necessary.

2720 Shelter Island Drive, San Diego, CA 92106 | Call +1 619-297-7426 | Email:

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