hi there,
There are many San Diego sail rentals to rent in and around the harbor, and you can even sign up for lessons.
If you have a well trained skipper in the group, you could charter a bareboat yacht and they're available for as little as a few hours up to an entire weekend or more.
If you don't want to set sail on your own, you could
hire one. For instance, Shelter Island
Sailing offers
rentals, complete with captains if needed.
Hope this helps
Vacationbuddy