Despite the fact that San Diego is California’s second-largest city, the mood is small-town and relaxed. It might have something to do with the weather, which in summer hovers around a near-perfect range between the upper 60s and upper 70s. The chill surf culture doesn’t hurt and neither do the 38 microbreweries in San Diego county—more per capita than any other U.S. county.
From the airport, head to The Pearl Hotel, a midcentury boutique stay with poolside movies and enough shag carpet, ’60s kitsch, and mod cocktails to make you feel like Don Draper in shorts. Jump on their fleet of beach cruisers to ride down to the surf, or venture inland to North and South Parks, cozy neighborhoods dotted with Craftsman houses.
The main North Park artery is 30th Street, where you’ll find a slew of cool boutiques, restaurants, and bars like Urban Solace, which “keeps it classy” with a painting of Ron Burgundy (aka Will Ferrell in Anchorman) and live music on its outdoor patio. Across the street is The Linkery, a hip, casual dinner spot of the sustainable persuasion—don’t miss the sausage taco. If you’re thirsty after your meal, take a bike cruise down to Hamilton’s Tavern in South Park. Toronado fans will appreciate the tavern’s lengthy beer menu, which offers up to 28 brews on tap.
The next day, drive 20 minutes north to La Jolla Cove’s La Valencia Hotel, a Spanish-colonial resort with an old-Hollywood vibe and dramatic views from its pool. From the cove, take a kayak adventure to the La Jolla cliffs and caves, rent stand-up paddleboards, or get some surf chops with a private lesson ($75 for an hour) from Surf Diva Surf School. For a midday rooftop snack, George’s Ocean Terrace is your best bet. Get the ceviche, and sip on a caipirinha while you watch the sea lions laze on the rocks below.
For the rest of the afternoon, check out Solana Beach’s Cedros Avenue, a design-lover’s heaven lined with airplane hangars that have been converted into stores and showrooms. Shop for cool housewares at SoLo, and stop in at Aaron Chang’s surf-art gallery to ogle his breathtaking photos of San Diego’s Black’s Beach, one of the premiere surfing destinations on the planet.
If you’re a golfer, you’ll want to play a round at ocean-flanked Torrey Pines Golf Course, home to the 2008 U.S. Open. Then get your spa fix at the The Spa at Estancia with a deep tissue massage, a salt water soak, and time in the eucalyptus steam room. Afterward, zone out by the outdoor fireplace in the attached hotel restaurant. If you can pull yourself away from the fire, head to the Grand del Mar’s restaurant Addison, winner of Wine Spectator’s Grand Award for two years in a row, thanks in part to wine director Jesse Rodriguez, former head sommelier at French Laundry.
That’s a pretty packed weekend itinerary, but on your way out of town, make time for one last stop. Grab a grilled mahi mahi taco to go from South Beach Bar & Grille in Ocean Beach. Eat it on the pier, watch the surfers show off, and soak up your last bit of SoCal summer sun before heading back to SF’s July fog.