Book Your Next Sailing Adventure Call +1 619-297-7426

Private and Group Sails

Sail San Diego is a leader in organizing any itinerary ensuring a great time is had by all! Our Captains are the best in the business and have hosted hundred’s of events.

Looking for a memorable way to Pop the Big Question? Sail San Diego has the perfect idea!

We are offering a 3- hour private sail working closely with you to make sure your proposal experience is exactly what you envision it to be. We can pretend to do sailing lessons, find a message in a bottle, have flowers hiding on board with Champagne as well as congratulations sign ready at the quick. Give the captain your camera and he will capture the surprise. If you can think of something unique or you need ideas we will enjoy helping while calming down anyone getting ready for the big day. This trip includes a nice variety of alcoholic and non-alcoholic beverages, snacks and all the amenities for comfort.. If you would like an audience bring up to four friends with you!

Price: $505.00 for the boat privately.
Call for times and details.

Enhance your experience with our premium wine―click here to learn more.

We have hosted so many proposals, all unique and successful! Yes, we are happy to report that we are 100 % with the answer being YES.

Did She say Yes a few years back?

This is a great way to celebrate the date. Anniversaries are always fun aboard a sailing vessel. Bring some friends to join in the fun.

"We love groups of 6 or more and will accommodate you through our bareboat program. Call for details"


Planning a Bachelorette Party?
Planning a party shouldn’t be a stressful occasion so sit back, relax and let us take care of the details!

2051 Shelter Island Drive, San Diego, CA 92106 | Call +1 619-297-7426 | Email:

Crafted with in San Diego by Creatively Disruptive © 2016