Have you heard of the “Brooklyn of San Francisco”? Ugh, the trope is so overused. Oakland is its own thing: home to some of the Bay Area’s best-preserved roots, where 1920s Art Deco buildings front Instagrammable cafes, bookstores, and plant shops, and an impossibly hip set park their fixies in front of historic Victorian landmarks they call home. There’s plenty of personality, from its thriving art scene to the political opinions expressed on signs in every window, and passion; the Black Panther Party was founded in West Oakland, and an active, tightly knit community is quick to take on police brutality and racial discrimination.

Take a quick and easy 20-minute train ride from downtown SF to spend a weekend in Oakland—or combine it with a trip to see friends at UC Berkeley, just two train stops away—and you’ll see why many locals would take “The Town” over “The City” across the water any day.

Where to Stay

Oakland’s colorful personality shows everywhere—even in its homes. Skip the just-okay hotels and get an Airbnb in a central, walkable location like the Lake Merritt neighborhood (Temescal is a little farther from downtown but also a great spot). You’ll find tons of eclectic options, with everything from a glamped-up vintage camper van, to a sailboat, to a Japanese tea house, but even the standard apartments are cute. Prices typically range from $30–$100 per night for a full apartment or studio for a couple people.

There are plenty of Airbnbs near Lake Merritt, from a glamped-up vintage camper van to a Japanese tea house. Getty

Friday Evening

Oakland has a ton of events in its streets, from farmers’ market to flea markets (so. many. markets.) to block parties, most of which operate on weekly or monthly schedules that locals know by heart. Don’t worry, though: You don’t have to keep track of what happens when—we’ve done it for you (though the website East Bay Fun Cheap is a trusty backup in case you want to stray from the schedule below). A regular on the calendar? First Fridays.

First Fridays in Oakland are a thing. The first Friday of every month, all of Oakland (and a lot of San Francisco) spills onto the streets of the KONO neighborhood (Koreatown Northgate), where several blocks of Telegraph Ave. are closed to traffic and filled with food trucks, art exhibits, shopping stalls, and live performers. Before sunset, the scene is pretty mellow, but once it gets dark the event turns into a huge block party filled with twenty-somethings collectively moving to whatever DJ is on the nearest makeshift stage. Food trucks and vendors rotate frequently, but one landmark is Korean Plaza (KP) Market, which turns its parking lot into a Korean food market with little plastic chairs and fairly priced dishes like the $5 bibimbap and japchae. Since it’s set back from the main block party, it’s the perfect spot to grab a breather when the streets get crowded. When you’re ready to check out the art exhibit portion of the event, step onto the sidewalks behind the rows of food stalls and walk into whichever galleries have their doors open that evening. (We love Johansson Projects and Warehouse416.)