There are several places in San Diego to take sailing lessons, or to rent small to large boats. I’m going to assume you want to do this since you are reading this post, so I won’t sell you on the beauty, peacefulness, and fun of sailing in San Diego harbor. It was always something that I had wanted to try, and I was not disappointed. I’m a retired Marine so I have access to lessons and boats on base which can save a lot of money. But you can also save money by looking for deals or by joining a sailing meetup group.
I took a basic sailing course at Fiddlers Cove Marina in 2007. The two-day course led to a certification for small sail boats. Since then I have been able to rent sail boats for very low fees on the two Navy Marinas in San Diego. I don’t go out as often as I would like to, but a couple of times a year I get the urge and head down to the harbor. At Fiddlers Cove I usually rent a 16 foot Catalina, these are small but very stable boats and are fun for sailing with 2-3 people. At the U.S. Navy Sailing Center Point Loma (April 2016 – which is now closed) I usually rent a 23 foot boat which has room for more people but it needs a lot more wind and is not as fun to sail, unless the wind is really strong.
If you can’t use the Navy Base Marinas, there are several other choices in San Diego to get your basic sailing certification. I’m listing the schools that seem to have reasonable prices. If you know of others, feel free to describe them in a comment.
Regardless of your level of experience level Meetup.com is another way to experience beginning to advanced sailing in San Diego. I haven’t tried this yet, so I won’t make any recommendations. Just search for sailing on the site and read the group’s description. I’ve had very good experiences hiking with Meetup groups in San Diego, so I would expect sailing would be great too.