S2 7.9 Bear Lake, UT
Cruising in San Diego is not all that. Sure the weather is nice but there really is not a lot of places to go.Not the same as Cruising in the San Diego bay but then I wouldn't have to drive all the way down the state of Calif to get to the boat.
If I were in your situation I would prefer to have my boat in Puget Sound or up in Canada. Find a marina near a few golf courses. You will have a vacation home in a cool place, and if you get good at sailing you have one of the best cruising grounds right outside the marina in somewhat sheltered waters.