For those of you have seen the movie Anchorman, the legend of Ron Burgundy coined the phrase "stay classy, San Diego". While you need to see that movie whether or not you are heading to San Diego, here is what you need to know for a trip to San Diego.
/ Stay and getting around /
Downtown, Hillcrest, the beaches (Pacific Beach/Ocean beach/Mission beach) or La Jolla are all good areas to stay since each area has restaurants and things to see. It depends on whether or not you are a beach bum or you prefer strict city life (not hard to figure out which one is preferred on thefreebohemian).
There are some buses and trams, but you can't go everywhere with public transportation. Renting a car is a must and a car gets you to where you need to go much faster usually. It is also nice to rent a beach cruiser (bicycle) or a Vespa to get around.
/ shop /
You can definiltely shop 'til you drop in San Diego. In Seaport village, Hillcrest or Ja Jolla you can find shops that are one-of-a-kind that sell vintage clothes or specialty goods, or just a good choice of merchandise not from your normal retail stores.
There are several malls in San Diego such as Westfield UTC at La Jolla, Fashion Valley or Westfield Mission Valley. You can also go shopping in Old Town San Diego, Gaslamp Quarter or the beaches (Ocean beach/Mission beach/Pacific beach).
Also, just about a 20 minute drive from downtown San Diego towards Mexico there is a huge outlet mall with lots of great stores. Remember to take the last exit before the border of Mexico.
/ Things to do (other than shopping) /
San Diego is most famous for the large quantity of places that serve fish tacos (and Taco Tuesday). However, there are so many different restaurants and kitchens to try in San Diego. You really can find something for everyone; ethiopian, junk food, sushi, thai, italian, spanish tapas, mexican, afghani, indian etc. There are a lot of restaurants in the area of Hillcrest, La Jolla, and the beaches especially.
If you are into sports, San Diego has a lot of options for you. Go check out college basketball or football, baseball with San Diego Padres or american football with San Diego Chargers. You can also travel to Del Mar to look at horse racing if that's your thing.
If you don't want to watch sports, but do sports yourself, there are plenty of opportunities to get your surf on or use the boardwalk for biking, running or rollerblading/skateboarding or other activities. There are also places where you can try stand up paddling or wind surfing.
There are many opportunities to visit museums or learn more about history; what about the USS Midway Museum?
If you like animals there are plenty of options depending on your wallet. You can go see the seals or sea lions at La Jolla Cove, or check out Sea World, San Diego Zoo or the San Diego Zoo Safari Park.
If you like going to concerts, every year there is a cityfest at Hillcrest with arts and music (hillcrestcityfest.com). There are also a lot of concerts at the outdoor venue at Chula Vista or San Diego theatre. However, you are still close enough to go to Los Angeles for a concert or weekend trip to Disneyland or Six flags. You are also close to Tijuana if you want to visit Mexico, just remember passport and/or visa restrictions. Another short trip is to Coronado with the beautiful beach and hotel.
If you like being out in the nature, go hiking in the beautiful cliffs of Torrey Pines. There is also a golf course there if you are into that.
Whatever floats your boat - San Diego probably has it. You can rent a house on the beach and just spend your days sunning and lounging around, however, as you can see by this post there is truly something for everyone in this California city.