The Harbor Island  Yacht Club is a good place to rent sailboats. The boats are very new and well maintained.  The smaller 22 foot sailboats are good for less experienced sailors. Those who haven't been sailing long might be a little intimidated by the really big sailboats. With a larger group, it's best to hire a captain to take the group out sailing on one of the large boats. The 42 foot boats are spectacular. Many local residents report nothing but great experiences here and would recommend it to anyone visiting or living in San Diego. Some people like to go out in the afternoon just as the breezes are picking up and the sun is starting to set. Bring a bottle of wine and appetizers. It's wonderful and pretty inexpensive.