4108 Adams Avenue, Kensington
Just starting out the evening and need to pre-game? Head to Kensington first. If beer’s your thing, Clem’s Tap House, which serves organized flights of fancy beers at reasonable prices. It’s more of a tasting room than a bar, and you can bring your own food from the deli or take-out spots nearby. You won’t get wasted, but you’ll be ready to take the night elsewhere.
4095 Adams Avenue, Kensington
Across the street, Village Vino is probably the top spot uptown for drinking wine and working through small plates of food. The wine list is curated from small vineyards, and the periodic wine tastings always illuminate something. You’re guaranteed to learn a thing or two while you catch a buzz.
2145 Fern Street, South Park
Eclipse Chocolat, newly relocated to scenic South Park, is one of the coolest spots for a special dinner before hitting the town. The chocolate-centric tasting menus are smart, affordable, fun, staged early in the evening, and light enough that they won’t send you into a food coma before you hit the club. They’re popular, so make a reservation.
2306 El Cajon Boulevard, University Heights
There is no better mid-week meat fix to be had than the Tuesday “steak night” at Gilly’s. Ten dollars gets you a steak, potato, and a salad on the open-air patio, chillin’ with a group of regulars who’ve been in on the secret for decades.
The Cellar Door has been blowing up since Logan and Gary started hosting dinner parties at their house in 2011. The pretension level of this entire movement is over 9000, and it requires a moderate degree of digital stalking to get a reservation, but there’s no denying that there’s something special about excellent multi-course dinners and drink pairings in a borderline speakeasy environment that bends the rules of conventional business.
1250 Prospect Street, La Jolla
If you’re feeling extra spendy, TBL3 at George’s California Modern is, I think, the most inspired, cutting-edge, gastronomical night out in town. Fourteen courses of food will blow your mind and change the way you think about eating. The restaurant needs a full week’s notice to prepare a menu and the night will be all about you and your party.
12905 El Camino Real, Del Mar
The coolest thing that’s hit San Diego in recent years is Cinepolis. The Mexican chain of luxury cinemas boasts leather recliners, in-show service, cappuccinos, steak dinners, wine, beer, gourmet popcorn, and blanket delivery if you get chilly during the film. If spending $50 on a movie is wrong, I don’t want to be right. Seriously.
4496 Park Avenue, University Heights
414 University Avenue, Hillcrest
Had your fun and need to refuel before calling it quits? There’s almost always some kind of weirdness going on at Lestat’s. The Normal Heights coffee shop that never closes is a haven for the off-kilter, vampiric night owls and insomniacs living out Reality Bites in real time. But it’s also a perfect spot to caffeinate, hydrate, and otherwise sober up before you go to bed. If you need real food, Jimmy Wong’s Golden Dragon (414 University Avenue, Hillcrest, 619-296-4119) is the place to go for drunken noodles and fried rice until 3am every morning. Few things sit better in a partied-out stomach, and it helps that the restaurant is soothingly decorated and cozy as can be. If the hour is really late, Lil’ B’s (2611 El Cajon Boulevard, University Heights/North Park, 619-296-8268) stays open from Friday night through Sunday morning. It’s a reincarnated Brian’s American Eatery with better decor and lower prices. It trumps Rudford’s for tastiness, and the menu is extensive enough that something is guaranteed to sound good, no matter how “over it” you are.
4701 Ruffin Road, Kearny Mesa
Since not everyone hangs out in North Park all the time, it’s good to know that Studio Diner provides all the after-hours grindage you could want north of the city. For whatever reason, they’ve melded chromed-out, mid-century Hollywood flair with an East Coast edge. They even have fried Ipswich clams (bellies intact!) on the menu, which every person in the whole entire world should experience at least once before they die.
3711 Sports Arena Boulevard, Midway District
There’s one very good reason that Du-par’s gets to wear the crown of midnight-munchie madness. That reason is pie. Sure, the restaurant has pot roast, chicken-fried steak, blue-plate specials, and “America’s best pancakes,” but it’s the beautiful display case filled with blueberry, gooseberry, pecan, cream cheese, coconut, and chocolate pie that draws late-night diners.
601 W. Washington Street, Mission Hills
But, if you really want to do it right, hit Donut Star for any kind of donut, at any time of day. There is no more satisfied guy than the man with a French cruller — or maybe a Boston cream — and a six-ounce cup of coffee at four in the morning when the bars are closed and it’s not quite time to be in bed.