Where to lay my head for a few days in San Diego?
March 7, 2008 7:39 AM 
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After a week-long business meeting in San Diego in April, I'd like to take a couple days of vacation to actually visit the city, but but I'm having trouble getting a handle on where to stay (and where to look for a place to stay?)
For my meeting, I'll be staying in the Gaslamp district (but with no time for any sort of sightseeing.) Afterwards, I mostly just want to decompress, see some pretty stuff, take some walks, eat at tasty restaurants, and have a decent local bar where I can drink some whiskey and talk to strangers.
From the little I've been able to find on what San Diego is "like", it looks like the neighborhoods in which I'd most like to chill out are Hillcrest/Normal Heights?
(By way of comparison, in San Fran I stayed in the Castro and in NOLA I always stayed in the Marigny. Tourist-district-central is generally not for me -- I do not think I'm going to want to stay in the Gaslamp.)
I generally prefer small inns, B&Bs, and the like. Guesthouses with shared baths are absolutely fine. (Dorm-style hostels, not so much.) Cheaper is better. Am I looking on the wrong internet? I'm not finding much.
P.S. I won't have a car and I'm not willing to rent one.
P.P.S.
Yes,
I saw these previous AskMes.
I can't think of anything that would fit the bill unless you went to Julian, a small mountain town about an hour east of San Diego. There might be smaller, quainter places in some of the beach communities like Ocean Beach, La Jolla, Cardiff, or Encinitas, but there's not much in the more urban areas, and certainly not in Hillcrest or Normal Heights.
I think the problem that you'll find is that some aspects of what you're looking for are plentiful in some parts of town, while other aspects are absent there but plentiful elsewhere, which means that you have to travel around a bit if you want to get the whole package, and then you need to have a car because the public transit between those places is absolute shit...and uh oh. Also, the way San Diego is laid out, there's neighborhoods that have little urbanized commercial cores surrounded by seas of single-family housing, so there can be a long trip between things to do, with a limited amount of options in the immediate area.
Hillcrest and Mission Hills (they're right next to each other) both have the bar scene and all the tasty restaurants, and they're easily walkable and relatively close to downtown and the airport so you wouldn't need to schlep too far with your non-car-ness. However, they're not much for hotels, much less small, quaint places. You might be able to find something in Banker's Hill (just to the south of Hillcrest), but then there's really not a whole lot to *do* in Banker's Hill. But, you'd be right between Hillcrest and downtown, with Balboa Park to your immediate east, so if you're okay with walking a mile or two, you'd probably be fine. Normal Heights is a little seedier than Hillcrest, and more residential oriented; University Heights is just to the west and about the same. They're nice neighborhoods, but the hotels aren't really someplace you'd want to stay.
After thinking about it a bit, I think your best bet might be Little Italy. Plenty of restaurants, a couple of good bars, and lots of stuff to walk around and see and it's really become more urbanized lately. It's kind of the artistic heart of the city, with a couple galleries and a lot of architecture offices and art studios. Kind of our knock-off version of the village in NY. A lot of the buildings are newer there and it's really coming up, but I think they might still have some of the types of places to stay that you're looking for; if not, there's a couple Best Westerns, or hotels on the northwest side of downtown will be within easy walking distance. There's also a trolley stop right nearby. There's a large outdoor art festival on the streets there in April, so you might want to check and see if your trip coincides with that, which would kind of be a bonus. Most of the stuff there is crap, but it's fun to walk around and find the few good things while making fun of the schlock. For bars, you'll either want the Princess Pub (an "English" pub), or the Waterfront, which is the oldest continuously operating bar in town. There's plenty of more fancy restaurants, but for simpler eats, you'll want to try out Filippi's, which has been operating since 1948. That doesn't seem so old for people from the east coast, but out here, that's basically the paleolithic era. Little Italy is basically bounded by San Diego Bay to the west, the 5 freeway to the east, Laurel St. to the north, and Beech to the south.
If not Little Italy, I'd look into the beach communities, but I'd probably avoid Pacific Beach, which is kind of a college party zone. Mission Beach might have some nice places to stay similar to what you're looking for, and it has plenty of bars. Not so much with the restaurants (although the Misison Cafe is there--go for breakfast or lunch), but it does have a historic wooden roller coaster. If you look into places up north, like Encinitas or Carlsbad, they'll be a lot more laid-back without as much to do, more chillax-worthy. La Jolla is expensive, but is incredibly scenic, with lots of nice walks, and quite a few nice stores and excellent restaurants, as well as more touristy places.
posted by LionIndex at 8:14 AM on March 7