San Diego is another strange place where the county sucks up almost all of the surrounding suburbs pretty far north. Basically until you get to North County and go through Del Mar to get to Solana Beach. But SB is an easy choice here anyway. Not quite as obnoxious and filled with horses as Rancho Santa Fe, or as obnoxious and filled with dudes in cherry-red M3s as Del Mar, or as damn far up north as Encinitas, Solana Beach is the more subtly cool North County town, with a fantastic beachfront, a subtle arts community, the OG Pizza Port (aka the grandest place to drink amazing beer, eat solid pizza, and play video games), and handsome people with toned calves walking around everywhere. And before you're like, "But Kevin! Del Mar has so many more restaurant options!" Well, look, you're right next door, so you can go eat and drink at them, too. -- KA
San Francisco/Oakland, CA: Larkspur
Where to eat/drink: Picco, Farmshop, Silver Peso, Perry's
Larkspur is one of those Northern California towns that seems made up, with that grand old-timey Downtown with a vintage theater, redwoods everywhere, and dads wearing straight-brimmed hats carrying longboards. But it is a real place, friends. And it truly is grand. Trying to get into SF for work? How about you commute via the Larkspur ferry, which takes you right to Downtown in 25 minutes. Or maybe you're trying to go to Oakland? The Richmond Bridge connects almost directly from Larkspur too. Food you crave? Picco is one of the great Northern California restaurants anywhere, and has a next-level casual pizzeria next door, Farmshop has fantastic cocktails and pizzas, Donut Alley has the best old-fashioned donuts in the country, and food trucks from SF and Marin come to Marin Country Mart on Sundays. Bars? The Silver Peso is a dive bar institution, and legendary SF bar/restaurant Perry's opened a satellite location this year, so you can get beers and watch games on a 60in TV hidden in a damn mirror.