San Diego Is Becoming Southern California’s Coolest City — And It Has Mexico to Thank

La Jolla community in San Diego
La Jolla, a beachside community north of downtown San Diego. Photo: Misha Gravenor

Walking to Chicano Park in San Diego’s Barrio Logan neighborhood, I got the distinct impression that I was lost. According to my phone’s GPS, I was less than a block away from the seven acres that locals had described to me as a stronghold of the city’s Mexican-American community. All I could see, however, was a colossal highway overpass — a sea of highway overpasses, actually. It was hard to imagine that the thing I’d come to San Diego hoping to understand — how the city is continually shaped and reshaped by its standing on the border with Mexico — would be revealed in what looked like an urban no-man’s-land.

But as I entered this imposing tangle of concrete, the atmosphere brightened. I saw majestic bands of color crawling up the gigantic pillars — dozens of intricate murals painted with the aggression of graffiti and the precision of fine art. This near-mystical constellation framed sculptures, plantings of cacti and wildflowers, a skate park, and swaths of grass where children played and people lounged at picnic tables painted in the colors of the Mexican flag.

Dining and street art in San Diego, California
From left: El Jardín co-owner Claudette Zepeda-Wilkins, a former Top Chef contestant, in the garden of her restaurant; a mural by Mario Torero in Chicano Park. Misha Gravenor

Chicano Park evolved from an act of protest. In 1970, residents of the predominantly Mexican-American neighborhood learned that the area, which had been promised to them for parkland, was set to be turned into a highway patrol station. Frustration had been mounting for decades among locals, who lost access to the waterfront when naval installations were built during World War II and, later, saw the neighborhood’s integrity suffer when it was rezoned for industry. Tired of feeling marginalized, hundreds of people occupied the land for 12 days, demanding to be heard. They were; the city backed off of its plan. In 2017, the park, which contains one of the largest collections of outdoor murals in the country, was designated a National Historic Landmark.

I didn’t know this history as I walked around. But I could feel it. A cross-cultural vibrancy percolates through San Diego in ways that are thrilling and unexpected, if a little hard to uncover. This aspect of the city is particularly potent throughout Barrio Logan, still a Mexican-American stronghold but hardly a stagnant one, as younger immigrants and transplants are changing the neighborhood in compelling ways. Earlier that day, I’d eaten a tasty lunch at ¡Salud!, a boisterous, newfangled taco shop on the main stretch of Logan Avenue, where piñata shops and galleries showing Chicano art have been joined by places like the vintage-vinyl shop Beat Box Records and the white-cube gallery BasileIE. After hanging around Chicano Park, I made my way to Border X Brewing, a Mexican craft-beer tasting room with a punkish vibe, where the Horchata Golden Stout offered yet another taste — subtle, delicious — of the ways San Diego is rediscovering and reinterpreting its heritage.

Dining and shopping in San Diego, California
From left: Por Vida, a café in San Diego’s Barrio Logan neighborhood; rare vinyl at Beat Box Records, also in Barrio Logan. Misha Gravenor
Orange Line

Prior to arriving, I hadn’t given much thought to the idea of San Diego as a border town. I wasn’t familiar with its longtime slogan — “America’s Finest City” — but that’s more or less the impression I had of the place. I knew it had a fine zoo, fine beaches, fine surf breaks, a thirst for fine craft beer, a fine military presence, and some of the finest weather on the planet, which goes a long way toward explaining why it’s often talked about as a fine place to retire. There are American cities I’ve never set foot in — Nashville, say, or Boston — that conjure up something more dynamic in my mind than San Diego, a sprawling metropolis of 1.4 million that I’d actually been to twice before but somehow retained no memory of. It was so fine, in my limited understanding, as to verge on forgettable.

Yet beneath that very fine façade is a singular culture built through crisscrossing. Lying between San Ysidro, the southernmost district of San Diego, and Tijuana, Mexico, is the busiest land border on the planet. Some 200,000 people cross there each day, for a multitude of reasons: Mexicans entering San Diego for work and school; Americans skipping into Tijuana for medical care, cheap groceries, and rollicking food and art scenes. The completion in 2015 of the Cross Border Xpress, a bridge linking San Diego to the Tijuana airport, has been a boon to tourism to the city and for San Diegans looking to travel throughout Latin America. While San Diego and Tijuana are two distinct cities in two distinct nations, they function more like a single megalopolis that happens to have an international border running through it.

Of course, that border has become an incendiary topic over the past few years, thanks to the national debate over immigration and polarizing discussions about “the wall.” During my time in San Diego, where I stayed at the Pendry, a chic hotel in the Gaslamp Quarter, I got the impression that locals have responded by embracing an aspect of their city that in the past they might have taken for granted. “The most interesting thing about San Diego is Mexico” is a common refrain—the implication being not just that you could head to another country for a raucous evening or affordable dentistry but that the border is what makes San Diego more than just a sleepy seaside town.

“I came here to live the California dream — beaches and sun — without really thinking about Mexico,” Toni Cass, a young musician from Florida, told me on my first night in town. Cass was my server at El Jardín, an inventive Mexican restaurant in the upscale Point Loma district. “Now I think of here and Mexico as the same place,” she went on, describing another country as if it were a neighborhood she was stoked to have discovered. Her girlfriend lives in Tijuana, and she spends time each week on both sides of the border.

Street art and dining in San Diego, California
From left: A mural off Logan Avenue; Provisional, the restaurant at the Pendry San Diego hotel. Misha Gravenor

We were joined by the restaurant’s chef and co-owner, Claudette Zepeda-Wilkins, a former Top Chef contestant with tattooed arms and dark violet hair. She was born in San Diego, raised in Mexico, and grew up going back and forth. “This restaurant is an extension of that,” she told me, explaining that she regularly goes to Mexico to scour for ingredients unavailable in the U.S. Her food was outstanding — crispy tuna carnitas, charred octopus sprinkled with pumpkin seeds and habanero pepper — and representative of a new development in the city’s culinary landscape. “High-end Mexican is harder to do here than other places,” Zepeda-Wilkins said. “There’s still a perception that Mexican food in San Diego is supposed to be cheap. I’d like to change that attitude, though it’s a challenge.”

That challenge speaks to San Diego’s complicated relationship with its neighbor and the city’s role as a microcosm of America’s ongoing reckoning with Mexico. If you are affluent and white, as many residents and visitors are, the border is easy to overlook. Whereas the density of Tijuana butts up against the gigantic wall that marks the border, the busiest parts of San Diego are 15 miles away, a geographic reinforcement that Mexico is “the other.” That San Diego is a big military town, with politics that have historically tilted conservative, further underpins this paradox.

For years this meant that many San Diegans thought of Tijuana as a kind of lawless playground, and a visit as a rite of passage for spring breakers. In the wake of the drug-cartel violence that erupted between 2008 and 2011, residents came to view Tijuana in a darker light: as one of the world’s deadliest cities, with the border serving as a means of protection rather than a portal. But as the violence ebbed, creative young Tijuanans reclaimed their city, experimenting with food and culture in ways their counterparts in San Diego began to notice. The irony is that by the time America elected a leader who made the border synonymous with strife, San Diegans had begun to appreciate Mexico as never before.

Where to eat and stay in San Diego, California
From left: Diners at El Jardín, a new Mexican restaurant in the Point Loma neighborhood; a suite at the Pendry San Diego. Misha Gravenor

If a restaurant like El Jardín aims to bridge the divide on a micro level, the city’s cultural institutions are doing the same on a macro scale. When I was in town, the excellent Museum of Contemporary Art San Diego, which has had a binational mandate since the mid 1980s, was showing an exhibition of works by 42 artists, half from San Diego, half from Tijuana. Since 2013, the museum, located in the heart of downtown, has operated a “field trip” program, taking locals and visitors into Mexico to visit artists’ studios and cultural institutions. “The idea was to inspire San Diegans to go across the border, enjoy a day out, learn about people living the border life and, in turn, learn more about themselves and their city,” Cris Scorza, the museum’s director of education and engagement, who cocreated the program, told me. Originally from Mexico City, she moved to San Diego from New York “for the U.S.-Mexico hybrid life that you can only live here.” The field trips, she explained, have empowered people who were once scared of Mexico to explore on their own. “That’s my favorite part,” she said. “First they came with us, then they started going over in the evenings for dinner.”

Orange Line

The more time I spent in town, the more I came to understand the border’s subtle influences. One of my most memorable meals was at Born & Raised, a lavish steak house in Little Italy that could double as the set of a Baz Luhrmann film: gaudy leather booths, green marble tables, glittery brass. Nothing about the experience seemed to exude a distinctly Mexican spirit. But this turned out to reflect my ignorance. I didn’t realize that one of the menu’s signature items — a Caesar salad made tableside — could be traced back to Caesar’s, the Tijuana restaurant where the salad is said to have been invented.

Similarly, had I not known better I would have thought the scene on Friday night at Bar Pink, in the trendy North Park neighborhood, could have been airlifted out of any American hipster enclave: loud music, dim lighting, twenty- and thirtysomethings shaking their bodies and sipping cheap beer. But the DJ was from Tijuana, and the night was part of a series called Grrrl Independent Ladies, which hosts female and nonbinary musicians from Tijuana, Los Angeles, and San Diego in venues in all three cities. It was created by Mónica Mendoza, a laid-back and fiercely intelligent 34-year-old architect and musician who grew up in Tijuana and conceived of the series as a means of tapping into, and broadening, the cultural singularity of the surrounding region.

Related: Free Things to Do in San Diego

“I’m a frontera kid,” Mendoza told me at the bar, using the Spanish for border, and explained that she started coming into San Diego as a child and then every day for school at 13. She got the idea for Grrrl Independent Ladies after hosting a festival in Tijuana. “I’m searching for a way to bridge Tijuana with San Diego and Los Angeles through music,” Mendoza said. “Obviously we’re not going to tear down the wall physically, but we can begin to tear it down through art. I have people come to a San Diego show and then I’ll see them in Tijuana at the next.” She paused for a moment, surveying the room, where an indie rock band from Los Angeles was preparing to take the stage. For all the activism behind the evening, it was also simply a whole lot of fun. “Nights like this are when you almost forget the wall is there,” Mendoza said. “It’s been amazing, especially in this political moment.”

Dining and drinking in San Diego, California
From left: Tacos at Border X Brewing, a craft-beer tasting room in Barrio Logan; Stephen Kurpinsky, beverage director at Hundred Proof bar. Misha Gravenor

That same night I visited Hundred Proof, a bar on the edge of the University Heights neighborhood, where I met Stephen Kurpinsky, who was two weeks into his position as the beverage director. A bearded and sardonic dude from San Francisco, he recently helped open Nórtico, an upscale speakeasy in Tijuana. Though he has lived in San Diego for 12 years, the experience changed his understanding of the region. “You’ve got southern Californian culture, which is basically L.A., right?” he said, pouring me a “split base” Old-Fashioned of mezcal and bacanora, an agave-derived liquor. “We’re still a bit player compared to L.A., and we probably always will be. But when you start thinking of this place as Cali-Baha, that’s when you realize how genuinely cool it is.”

Kurpinsky attributed his passion to his love of classic cocktails and his distaste for the political climate. “I can’t tell you how awesome it is to be involved in opening a bar in Mexico while we have a president trying to build a wall,” he said. “The craft cocktail scene is still so new there—it has that addictive kind of excitement. And it’s a two-way street. In Mexico, there’s a showmanship to bartending, with old-school twirling of glasses and dramatic pours, which I’ve started incorporating myself. I taught them about making classics. They taught me how to make a performance for the customer.”

He paused for a moment, before fixing me with a curious stare.

“Dude,” he asked, “have you gone over to Mexico yet?”

Orange Line

This had become something of a running theme during my visit: all this talk of the cross-cultural fluidity that makes San Diego unique, followed by the casual suggestion that I make a trip across the border. I’d explain that, great as that sounded, I didn’t think I had the time. “What do you mean?” I’d invariably hear. “You just take an Uber to the border and Uber around Mexico!”

On my last day in town, I spent the morning hiking at Torrey Pines State Natural Reserve, reveling in the pink-tinged cliffs and pristine coastline, then decided to drive south and venture across. Just before the border, a sign reminded travelers that marijuana, now legal in California, cannot be brought into Mexico, a nation long associated with the drug trade. While car traffic can bottleneck at certain hours, crossing by foot was no more of a hassle than picking up my rental car earlier in the week. I parked, walked to the border, flashed my passport, and was in Mexico less than half an hour after being on the beaches of San Diego.

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In Tijuana, I was met by Ruffo Ibarra, the gregarious chef and owner of Oryx Capital, a local gastropub. The restaurant houses Nórtico, the bar that Kurpinsky had helped open. We spent the day doing what a lot of people go to Mexico to do: eating and drinking. We started off at Telefónica Gastro Park, a kind of bohemian collective of food trucks where the food ranges from Greek to Korean, before making our way to Plaza Fiesta, which has nearly a dozen craft-beer tasting rooms. In a sense, it reminded me of Chicano Park, an unexpected place where cultures braid to create something astonishing. “The influence goes both ways,” Ibarra told me as we sampled beers at Insurgente, a minimalist taproom. “We gave San Diego the fish taco. They gave us craft beer!”

After dinner at his restaurant, and a few superb cocktails at Nórtico, I caught an Uber back to the border, crossed, hopped in my car, and was soon back in the heart of downtown San Diego, where I entered the polished lobby of the Pendry. Sun-burnished guests jostled for drinks at the bar. The delicate thump of music could be heard from a pool party. It was a surreal moment. Here was the San Diego I’d imagined before the trip — a very fine place, indeed, though one made all the more fascinating because of what I now knew existed outside these walls.

Waves crashing at La Jolla beach, in San Diego, California
Waves crashing at La Jolla. Misha Gravenor

The New San Diego

Allot three or four days to soak up the cross-cultural exchange enlivening the city — and make sure to include a trip across the border.

Getting There and Around

Multiple carriers fly direct to San Diego International Airport. Ride-share apps are great for moving around town, but renting a car is ideal, given the city’s sprawl.


The Pendry San Diego (doubles from $268), located in the historic Gaslamp Quarter is hands down one of the most stylish. There’s plenty to do within walking distance, and the pool scene is perfect for a dose of pure SoCal glitz. For a touch of eccentricity, try the Lafayette Hotel (doubles from $129) in trendy North Park; its pool was designed in 1946 by Tarzan actor Johnny Weissmuller. Or for five-star indulgence try the palatial Fairmont Grand Del Mar (from $350).

Eat and Drink

Logan Avenue, in Barrio Logan, is home to an emerging food scene. I had a great lunch at ¡Salud! (entrées $3–$12), a fun taco shop. Border X Brewing specializes in Mexican craft beer, like a saison with traces of hibiscus. Por Vida, a café, makes a mean horchata latte. At El Jardín (entrées $19–$42), in the Point Loma neighborhood, Claudette Zepeda-Wilkins channels her border-straddling upbringing with inventive dishes. If you’re in search of a more decadent experience, plan an evening at Born & Raised (entrées $42–$88), a steak house in Little Italy with lavish décor. Polite Provisions offers exquisite cocktails, while Bar Pink, in North Park, features DJs and live music.


Logan Avenue is great for strolling and browsing. I enjoyed Beat Box Records, a no-frills vinyl outpost specializing in rare soul and funk, and Simón Limón, a shop that showcases housewares, jewelry, and crafts made by local artists.

Art and Culture

Chicano Park, in Barrio Logan, is a living monument to the city’s Mexican-American heritage. Located under a highway overpass, it contains one of the largest collections of outdoor murals in the country. Around the corner, BasileIE, a gallery in a former grocery, focuses on emerging artists.

Outdoor Experiences

There’s no shortage of natural beauty in San Diego, from the white sands of Coronado Beach to Mission Bay’s pristine cove. But my top choice is Torrey Pines State Natural Reserve, where a hike along the sandstone cliffs above La Jolla offers superb views of the Pacific.

Crossing the Border

No trip to San Diego is complete without a visit to Tijuana. The easiest way to enter is by foot. Take an Uber to the crossing — or drive and park. My day trip was idyllic: lunch at Telefónica Gastro Park, a food truck collective; craft beers at the tasting rooms at Plaza Fiesta; and dinner at Oryx Capital (entrées $13–$30), an upscale gastropub with a speakeasy-style bar.

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