From The Docks – San Diego Staycation

Do you like the idea of going on an adventure but staying close to home, here in San Diego? After all, why would you want to leave the greatest City in the World, with the best weather, when you already live here? Plan your next staycation here with us at Sail San Diego & come out for a relaxing SAIL!
Experience your own City from a differint vantagepoint, the water instead of land. On our sunset sails, you’ll take in the sights of the Downtown San Diego City skyline while sailing. As a San Diegan, you don’t need to fly thousands of miles to experience your own thrilling adventure at sea!
Curious about trying your hand at sailing? You could even sign up for a sailing lesson on one of our yachts and experience sailing hands-on! Our private marina is located on Shelter Island, a hidden gem of the San Diego area.
If you’re going out on a Day Sail, arrive a little early & grab a coffee at one of the local cafes. Pro-tip from our office manager Pastry-Eating Pete: As of 2022, Coffee Hub (walking distance) began baking their own pastries in-house! Want to make dinner reservations for after your sail? You can do that too! Brigantine, Pizza Nova, Pummaro, Pomodoro & Miguel’s are a few of our staff favorites.
San Diego has some of the best sailing here on the West Coast! Come experience it for yourself in your own City!

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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