WHEREVER you are right now, there’s a very good chance the weather is much nicer in San Diego. California’s second most populous city has long used its relentlessly pleasant climate to lure travelers to attractions like the USS Midway, SeaWorld, more than 90 golf courses and roughly a bazillion miles of beaches and hiking trails. Rarely does a sneak attack of cold or wetness ruin a weekend visit, even in the dead of winter. Indeed, investing in a San Diego vacation is as safe a bet as spending the same amount on T-bills. If the city has traditionally been knocked for anything, it’s that very safeness; a detour here ranks as low on the daredevilry scale as those T-bills. When East Coast culture vultures have come west looking for a dose of California cool, they’ve gravitated to San Francisco or Los Angeles.
San Diego is finally catching up. In recent years, it’s deepened its commercial and cultural ties with Mexico’s Baja region, becoming a far more compelling destination. Look to the flourishing galleries in Barrio Logan and a new focus on sophisticated Mexican cooking. The beer scene is both expansive and experimental, thanks to rivalries among San Diego’s roughly 120 breweries, while the conversion of the Naval Training Center at Liberty Station into a sprawling district focused on food, the arts and entrepreneurship is changing the very map of the city. Excellent food, culture, nature—and beer? That, as local (albeit, fictional) anchorman Ron Burgundy would say, is “kind of a big deal.”
DAY ONE // FRIDAY
8:30 p.m. Arrive at San Diego International Airport, which is about as conveniently located as an urban airport can be—less than 3 miles from downtown. Pick up your rental car and either drive 15 minutes to the Pearl Hotel in Point Loma, a refurbished 1960’s-vintage motor lodge a block from America’s Cup Harbor (thepearlsd.com, from $100 a night) or, about 30 minutes north of downtown to Fairmont Grand Del Mar for a more classically luxurious resort experience, including an 18-hole golf course and spa (from $495 a night, fairmont.com).
10:00 p.m. Choose your own adventure for dinner. Old-school San Diego or new? For the old, there’s the unreconstructed 1950s charm of the horse racing-themed Turf Supper Club in the neighborhood of Golden Hill. Settle into one of the banquettes ringing the dim red-lit dining room. Order a gimlet while you scan the menu, where (raw) steaks and kebabs dominate. Diners cook their own dinners on the large copper-hooded gas grill at the center of the restaurant, often chatting amiably with each other—like a DIY dinner party (1116 25th St., turfsupperclub.com). More newfangled: Just five minutes further away, in South Park, is Kindred, a cocktail bar and vegan restaurant with a death-metal-meets-Victorian-parlor aesthetic. Don’t be intimidated—the crowd is eclectic, the staff welcoming. Try the “charcuterie” plate with slices of spiced seitan and the anything but “Boring English Trifle” that shows just how unnecessary dairy can be (1503 30th St., barkindred.com).
DAY TWO // SATURDAY
8:15 a.m. Wake with the fishes at the Tuna Harbor Dockside Market and watch boats pull up to the dock with that day’s catch. Families come here early to buy sea urchin, giant crabs, live octopus and whole tuna, which amazingly sells for less than $4 a pound (879 West Harbor Dr., thdocksidemarket.com).
9 a.m. Drive about 20 minutes to Madison in University Heights. Yes, the beet waffles are a sight to behold, but it’s the back patio that’s the true stunner (4622 Park Blvd., madisononpark.com).
10:30 a.m. Ten minutes’ drive down Park Blvd, is Balboa Park, the 1,200-acre museum- and garden-packed centerpiece of the city. The San Diego Museum of Man makes anthropology exciting, with a fascinating, and yes, fun exhibition on cannibalism (1350 El Prado, museumofman.org). Sign on for a climb of the museum’s California Tower, during which you’ll get an overview of the history of the park and views all the way to Tijuana. Back on the ground, take a trip back in time aboard an Electriquette—a battery-powered wicker cart that toddles along at 3 mph. These were a sensation during the park’s earlier incarnation as the home of the 1915-16 Panama-California Exposition (wickercarts.com).
12:30 p.m. Ten minutes’ drive further south puts you in Barrio Logan, the heart of Chicano San Diego. Join the line for tacos and nachos at ¡Salud! which is decorated with posters and car parts from a 1962 Chevy Impala, celebrating SoCal lowrider culture. The Barrio taco comes on a thick, hand-pressed flour tortilla and a ladleful of carne guisado—stewed beef topped with beans and slivers of nopal-cactus (2196 Logan Ave., saludsd.com).
1:15 p.m. Explore Barrio Logan’s galleries and shops. Start at Vecindad del Barrio, a small complex of shops and art spaces including Por Vida coffee shop, where you can browse a small, well-curated collection of art and T-shirts, including work from Tijuana street artist known as Panca. If you need a pick-me-up, try the cold-brew coffee sweetened with horchata (2146 Logan Ave., vecindaddelbarrio.com).
3:30 p.m. Walk five minutes up Logan Avenue to one of the city’s great public art spaces, Chicano Park. Since the early 1970s, the massive roadway-support pillars connecting the Coronado Bridge with I-5 have sported epically scaled murals depicting Latino life and legend. The park is also home to a skate park, playground and pavilion called the Kiosko, modeled after Aztec and Mayan designs (chicano-park.com).
4:30 p.m. Sunsets are treated with the seriousness of a secular sacrament around these parts. Take it in at Luscomb Point in Sunset Cliffs (Hill St. and Sunset Cliffs Blvd).
7:30 p.m. For dinner, go to Juniper & Ivy in Little Italy. The ecumenical menu might include a raw seafood medley with sea urchin, a Moroccan-tinged lamb and the Yodel dessert, a supersize rolled devil’s food cake. Waitstaff have to speak loudly to be heard over the booming ’80s-heavy soundtrack (2228 Kettner Blvd., juniperandivy.com).
9:30 p.m. It’s a five-minute walk up Kettner Blvd. to the Casbah, a landmark of the San Diego music scene. It’s loud, dark and a bit grungy, but a smart booking record and low ticket prices (usually less than $20) compensate. You may be able to brag in a few years that you saw some superstar band in a tiny club way back when (2501 Kettner Blvd., casbahmusic.com).
11:30 p.m. About a mile away, in the restaurant Craft & Commerce, look for the walk-in cooler door. Behind it is the False Idol tiki bar serving exotic cocktails like the “Alkala the Fierce,” made with chai-infused-bourbon and pimento dram, among other oddities, and presented with theme-park-grade theatrical flair. Reservations recommended (675 W. Beech St., falseidoltiki.com).
DAY THREE // SUNDAY
8:30 a.m. Head to the locally famous World Famous, in Pacific Beach, for breakfast with a view. Take a boardwalk-side table, and watch the surfers while you eat eggs Benedict or an off-menu bowl of pozole (711 Pacific Beach Dr., worldfamouspb.com).
9:45 a.m. Continue driving 30 minutes north to the 1,500-acre Torrey Pines State Natural Reserve home of one of the rarest species of tree in the world. Walk off breakfast on the trails to Razor Point and Yucca Point for incredible views of the striated sandstone cliffs dropping down to the ocean (torreypine.org).
11:45 a.m. Appetite restored, it’s just a 15-minute drive back down the coast to Galaxy Taco in La Jolla for lunch. The octopus tostada—with a lashing of charred orange and habanero salsa—is electrifying (2259 Avenida De La Playa, galaxytaco.com).
12:45 p.m. It’s a five-minute drive to The Cave Store, a souvenir shop, and then, from inside, 145 steps down a hand-dug tunnel to Sunny Jim’s Cave, which opens onto La Jolla Bay. Legend has it the cave got its name from L. Frank Baum of Wizard of Oz fame, who thought that the mouth of the cave looked like Sunny Jim, the mascot of Force Wheat Cereal, popular early in the 20th Century (1325 Coast Blvd., cavestore.com).
1:15 p.m. Return to the surface and wander down shoreside Coast Blvd. Watch people on the beach below make bad decisions, like taking selfies with sea lions (they bite), while you make a good one—like stopping at Sardinian-style gelateria Bobboi. Sample the “Pistacchio della California,” made with Santa Barbara-grown pistachios (8008 Girard Ave., La Jolla, bobboi.com).
1:30 p.m. While the USS Midway is San Diego’s best-known military attraction, it’s hardly the only one. Instead, try the low-key, deeply engaging Flying Leatherneck Aviation Museum, a 20-minute drive east at the edge of the Marine Corps Air Station in Miramar. Among the museum’s collection of aircraft is the “Lady Ace 09,” the helicopter that evacuated the U.S. Ambassador from the South Vietnamese embassy during the fall of Saigon (4203 Anderson Ave., flyingleathernecks.org).
2:45 p.m. Many of San Diego’s more than 120 tiny breweries are found in the industrial parks of Miramar, several within five minutes’ drive of the Flying Leatherneck Aviation Museum, including the Mikkeller tap room, where you can try curious concoctions like Beer Geek Brunch, an imperial oatmeal stout aged with Heirloom Weasel coffee (9366 Cabot Dr., mikkellersd.com). Nearby, Setting Sun Sake brewery offers traditional, fruit- and hop-infused sake on draft (8680 Miralani Dr., settingsunsake.com). Keep to tasting-size pours if you’re driving, of course, or consider the chauffeured tour Brew Hop offers (brewhop.com).
4:15 p.m. It’s about a 30-minute drive back down to Liberty Station, a former Naval Training Center, which has been turned into a city within the city, colonized with museums, restaurants, a food hall, galleries and shops. The ComicCon spirit is alive year round at Comickaze Comic Books and More. Be sure to browse surfboards and housewares at Moniker General before heading out (libertystation.com).
7:30 p.m. Drive to the Red Door in Mission Hills for dinner. You’ll see a dish called Farm-to-Fork heading to most tables. It’s a mélange of vegetables some harvested that morning from the owner’s farm, sauteed with a garlicky chimichurri sauce (741 West Washington St., thereddoorsd.com).
9:30 p.m. Ask San Diego bartenders where they like to drink, and many will tell you Sycamore Den in Normal Heights, a 15-minute drive away. The décor is stylish ’70s-suburban-rec-room, complete with a conversation pit by the fireplace (3391 Adams Ave., sycamoreden.com).
DAY FOUR // MONDAY
8:30 a.m. Join the breakfast queue at Las Cuatro Milpas (don’t worry, it moves quickly). Linemates might tell you the thing to get here is a bowl of chorizo and beans (with eggs, if you want) along with the fresh-off-the-griddle flour tortillas. Those people are not wrong (1857 Logan Ave., 619-234-4460).
10 a.m. A 10-minute drive north is the historic district of Bankers Hill, known as much for the swaying footbridge over Spruce Canyon as it is for its architecturally eclectic homes—including a few designed by early modernist architect Irving J. Gill. The Save Our Heritage Organisation offers downloadable walking-tour maps (sohosandiego.org).
11:30 a.m. The tide pools at Cabrillo National Monument are a 25-minute drive away. Explore on your own, or if you get there at low tide, you may be able to join a ranger-guided tour. The drive down to the monument takes you through the breathtaking Fort Rosecrans National Cemetery. From the monument itself, you can watch ship traffic, including aircraft carriers, move in and out of San Diego Bay (1800 Cabrillo Memorial Dr., nps.gov/cabr).
1:30 p.m. A casual dockside restaurant at America’s Cup Harbor, Mitch’s Seafood serves everything from gold-spotted bass and swordfish to baja shrimp, making their way into sandwiches, salads, tacos and ceviche. Take a seat at the rail outside to watch sea lions frolic among the yachts (1403 Scott St., mitchsseafood.com).
3 p.m. Artifacts of San Diego’s seafaring history can be found at what might just be the city’s coolest shop, Maidhof Brothers Shipware Merchants, a 10-minute drive away. Looking for a working telephone from the bridge of a WWII-era aircraft carrier? Got it. For an easy-to-carry souvenir, grab a vintage paper model kit of the SS Normandie (1891 San Diego Ave., seajunk.com).
4 p.m. Move from the past to the present at the Museum of Contemporary Art San Diego, which has a reputation for showing cutting-edge work that often interrogates the deep, complicated relationship between the U.S. and Mexico (1100 Kettner Blvd., mcasd.org).
5 p.m. Walk four blocks up Kettner Boulevard. for a final bite before heading home. Chef Javier Plascencia’s modern Mexican restaurant Bracero has been lauded as one of the best new restaurants in America, and whether you’re just having a few happy-hour tacos at the bar or settling in for a tasting menu in the dining room (pray that the Crispy Brisket and Short Rib is still on offer), it won’t take long to see why (1490 Kettner Blvd., bracerococina.com). The airport is about a 15-minute drive.