As California’s oldest city marks its 250th birthday, a hometown writer looks back on how the place has changed since 1769 …  and within his own lifetime. 

Photographs by James Tran.

During his epic voyage along the west coast of North America in 1542, Spanish explorer Juan Rodríguez Cabrillo supposedly called southern California the “land of everlasting summers.” True or not, those words fittingly describe my April cruise across San Diego Bay aboard a replica of Cabrillo’s flagship, the San Salvador. The sky is cloudless, the sun is plentiful, and temperatures are warm enough for shorts and T-shirts. 

“I wasn’t planning on raising the sails today,” says Captain Jack Pinhero from his perch on the upper deck, “but I don’t wanna waste this breeze.” So up they go, great rectangles of parchment-colored canvas hoisted into place by the crew and a few eager passengers.

Sailing through the harbor entrance at the end of Point Loma, the 200-ton galleon—a relatively recent addition to the historic armada at the Maritime Museum of San Diego—fires a salute from a swivel gun as we pass the Cabrillo National Monument, which marks the spot where Cabrillo became the first European to set foot on these shores. And suddenly we’re out in the open Pacific, cutting across kelp beds as a steady wind takes us south toward Mexico. 

We cruise past the great sweep of Silver Strand Beach and the sand dunes of Border Field State Park, all the way down to Tijuana, where, within eyeshot of the city’s seaside bullring, Captain Jack brings the San Salvador around. Not much later, the first mate shouts, “Whale off the port bow!” It’s a solitary gray, migrating north toward Arctic waters after wintering in Baja. The barnacle-encrusted leviathan swims alongside us for a while before sucking in a deep breath and disappearing below the waves. 

Point Loma comes into view again. Inhaling the salty air, listening to the creak of the galleon’s rigging and the snap of the sails, I try to imagine what Cabrillo and his crew might have felt as they probed this uncharted coast for a safe anchorage. But it’s impossible. However alien these shores must have seemed to them, San Diego is a lifelong—and very welcome—home port for me.

I haven’t always felt that way. Struggling to come to terms with the place of my birth, I left San Diego when I was 18 and vowed never to return. Aspiration was the root of the problem. I wanted to be a writer, and to a pretentious teenager, 1970s San Diego just wasn’t all that inspiring. Indeed, I saw it as a city of lost dreams, a place with great potential that invariably fell short: the oldest city in California, but not the state capital; an almost Hollywood (more than 100 silent films were made here in the 1910s) that lost out early to Los Angeles. The best gig Whoopi Goldberg could land here back in the day was waiting tables at a local diner. And Eddie Vedder didn’t become the king of grunge until he fled north to Seattle and formed Pearl Jam. 

Three months after graduating from high school, I packed my bags, said goodbye to my folks, and hit the road in search of a muse. My aims were clear: I wanted respect, I wanted success, I wanted to grow up in a hurry. It wasn’t until I moved back to San Diego two decades later, in 1995, that I realized my hometown had been craving many of the same things. 

By the time I returned, the city had doubled in population and pushed its suburbs far into what I remembered as flower fields, dairy farms, and eucalyptus groves. Downtown was spangled with high-rise hotels and condo blocks, the bay lined with racing yachts rather than tuna boats. Economically, San Diego had undergone nothing short of a revolution. It was still a navy town, to be sure. But the aircraft and rocket factories of old—jobs that had brought both my mother and father here—had been replaced by a mini Silicon Valley of biotech and telecom startups. 

The neighborhoods I knew from my youth had changed completely as well. Hillcrest, the dowdy inner-city area where my grandmother once lived, had morphed into a vibrant alternative-lifestyle hub. The stretch of India Street where many of the old tuna-fishing families had lived was now called Little Italy, their homes and little aromatic cafés replaced by scores of trendy restaurants. 

And then there was the Old Town district. Founded in 1769, this was California’s first European settlement, which is why it’s often called the birthplace of the state. But it was kind of a dump when I was a kid. Other than the Tamale Factory—a long-gone eatery that kick-started my love affair with Mexican food—and the deliciously haunted Whaley House (a museum since 1960, it sits on the spot where the town gallows was located in the days before San Diego had a proper courthouse), there wasn’t much reason to go there. But things improved after the government declared half of Old Town a state historic park and began restoration work. Now, its old adobe and wooden buildings host museums, art galleries, and gift shops.

I’ve been to Old Town countless times since moving back, most recently to research my novel Nemesis, a whodunit set in the rough-and-tumble San Diego of the 1880s. Touristy it may be, but the area around the park’s grassy central plaza is undeniably evocative of rancho-era California. I’m particularly fond of the Cosmopolitan Hotel. Since being built almost two centuries ago as the home of a wealthy Californio family, the building has served as lodgings for stagecoach passengers, a boarding house, and an olive-pickling factory. In 2010, after extensive renovations, it was reopened as a hotel, one replete with copper tubs, brass beds, and other Victorian-style decor. The carved mahogany bar in the Cosmo’s saloon is said to have once been owned by Wyatt Earp. 

Down along Old Town’s main drag, though, the scene is nothing like it used to be, at least not on the March evening that I visit. When I was in high school, we used to slip across the border into Mexico because there weren’t so many cool places for young people to hang out after dark. Now, San Diego Avenue is chockablock with restaurants and bars that draw crowds of hard-partying college kids during spring break—a hotbed of tequila shots, fishbowl margaritas, and mariachi bands. 

To escape the throngs, I duck into a cozy mezcal joint called Tahona and order a shot of El Jimador Blanco. From my stool at the bar, I can look straight out the window onto the darkened graves of the old El Campo Santo Cemetery, or at least what remains of it—much of the original burial ground was paved over in the 1940s to make way for San Diego Avenue. It’s a spooky spot. One of the most-often reported ghost sightings is that of “Yankee Jim” Robinson, who was hanged (for stealing a rowboat) where the Whaley House now stands and is said to haunt both sites. 

Pointing my chin at the graveyard, I ask the bartender if he’s ever seen anything strange out there. He shrugs. “Only if you think drunken college students are strange.”

After California became part of the United States in 1848 at the end of the Mexican-American War, San Diego’s center of gravity shifted from the Spanish settlement of Old Town to an American-built “New Town” beside the bay that would eventually evolve into today’s high-rise-filled Downtown and the Gaslamp Quarter. You can still find relics of that era today, places like the Tivoli Bar on Sixth Avenue, where I meet up with local historian and amateur actor Jim McVeigh.

“Back in those days, this new part of San Diego was split into two completely different worlds,” McVeigh explains as he leads me on a historical walking tour. “You had the area around Horton Plaza where the respectable people lived and worked. And you had the area where we are right now. It’s called the Gaslamp now, but they used to call it the Stingaree because sailors coming off ships were just as likely to get ‘stung’ by the conmen and cathouse ladies as by the real stingrays in the bay.”

According to McVeigh, San Diego back then was just as badass as Deadwood, Dodge, or Tombstone in the Wild West days—a combustible blend of gunslingers and sailors, cattle ranchers and swindlers, professional gamblers and desperados from nearby Baja California. Among them was Wyatt Earp, who made his way to San Diego after the shootout at the O.K. Corral. 

The Stingaree flourished until the early 20th century, when reform-minded city officials began shutting down the neighborhood’s drug dens, gambling halls, and brothels. The cleanup was largely triggered by San Diego’s hosting of the 1915 Panama-California Exposition, for which much of Balboa Park—including San Diego Zoo, the California Tower, and the other Spanish Colonial Revival buildings along El Prado—was originally erected. Raided and partially razed, the Stingaree fell into decline. By the time I came along, it was San Diego’s version of Skid Row. 

McVeigh credits the revitalization of the area to Ingrid Croce—the widow of the legendary folk singer Jim Croce—who, in 1985, opened Croce’s Restaurant & Jazz Bar on the ground floor of the historic Keating Building. That kicked off a revival that’s created one of America’s liveliest nighttime entertainment districts, a mix of snazzy bars, dining rooms, music joints, and comedy clubs that today encompasses live piano bars like The Shout! House and the Hakkasan Group’s Vegas-style nightclub Omnia. Some stylish hotels have moved in as well, most recently the Pendry, with its rooftop lounge and ground-floor beer hall; and the millennial-friendly, marine-themed Moxy, where guests check in at the bar. 

A 15-minute drive through the scrub-covered canyons of Balboa Park brings you to another of the city’s buzziest neighborhoods, North Park. Originally a streetcar suburb, there wasn’t anything special about the place when I was growing up. Now, thanks to a couple of decades of gentrification and hipsterfication, it’s home to an arts district and a slew of cocktail bars and craft-beer tasting rooms. The epicenter of the action is the intersection of 30th Street and University Avenue, just down from where the North Park Theatre movie house put down roots in 1929 (the building is now a concert venue called the Observatory). On a recent visit, I grabbed a “Holy Mole” burrito at the newest outpost of taco chain Lucha Libre, whose flamboyant decor (bright pink walls, a mini wrestling ring) sets it apart from the city’s surfeit of no-frills taquerias. 

Mexican food is San Diego’s unofficial cuisine. Unlike the rest of the city’s culinary landscape, however, it hasn’t evolved all that much over the years, despite memorable recent attempts by chefs like Claudette Zepeda-Wilkins, a James Beard Award semifinalist whose upscale El Jardín restaurant shuttered in July just 13 months after opening. The issue was one of perception. San Diegans will happily splurge on French or Italian cuisine, and they’re given good reason to at recent arrivals such as Jeune et Jolie in Carlsbad and Il Dandy in uptown Bankers Hill. But Mexican is supposed to be simple, cheap, casual.

Which explains the enduring appeal of Las Cuatro Milpas, a third-generation hole-in-the-wall that has been serving authentic, affordable south-of-the-border street food since it opened on Logan Avenue back in 1933. Located in the predominantly Mexican-American blue-collar neighborhood of Barrio Logan, the cash-only taqueria is known for its long lines and loved for its tamales and freshly rolled tortillas. There are seats inside, but a better option is to grab your order and walk over to a picnic table at Chicano Park. This three-hectare community green space is situated beneath the overpasses of the San Diego–Coronado Bridge, whose retaining walls and pylons were painted with dozens of murals in the 1970s. The artwork celebrates Chicano culture: here, a scene from Mesoamerican mythology; there, a vision of the Virgin of Guadalupe or Frida Kahlo or Che Guevara. One of the largest collections of outdoor murals in the country, the park was designated a National Historic Landmark in 2017.

Barrio Logan has not been immune to the creep of hipsterfication that has transformed so many other San Diego neighborhoods, but it remains a bastion of cultural diversity, with progressive art spaces such as BasileIE and San Diego’s only Latino-owned craft brewery, Border X, where owner David Favela makes beers like hibiscus-and-agave flavored Blood Saison and a cinnamon-y Horchata Golden Stout. Every summer, he also hosts Chicano-Con, a light-hearted community event that puts a Latino spin on San Diego’s famous comics convention.

Comic-Con itself is held three kilometers to the northwest in a massive bayside convention center that attracts thousands of sci-fi and superhero fans during the show’s July run. But the downtown waterfront, once the domain of naval ships and tuna boats, swarms with cruise-ship passengers and other tourists year-round. One attraction is the aforementioned Maritime Museum, whose armada of historic and reproduction vessels includes not only the San Salvador, but also the iron-hulled bark Star of India (built in 1863, she is the world’s oldest active sailing ship) and the replica British frigate that Russell Crowe skippered in the movie Master & Commander: The Far Side of the World. Another draw for history buffs is the decommissioned aircraft carrier USS Midway, which was converted into a floating museum in 2004. 

After my cruise aboard the San Salvador, I strolled along the waterfront promenade to take in the flashy yachts and gleaming new hotels and condo towers of the Marina District, a shoreline once dominated by warehouses. It’s not without its modern charms. But with selfie-takers thick on the ground, I quickly beat a retreat. 

Thankfully, some things never change. Like the surf scene. Because if there’s one thing that has defined San Diegan culture during my lifetime, it’s the shoreline lifestyle spawned by the men and women who go down to the sea with boards every day.    

Local hangouts such as La Jolla, Del Mar, San Onofre, and Swamie’s all get a mention in The Beach Boys’ “Surfin’ U.S.A.” When local filmmaker Bruce Brown made a documentary called The Endless Summer—universally hailed as the greatest surf movie of all time—one of the three dudes he chose to hang ten with around the world was Mike Hynson of Pacific Beach. Around that same time, a largely unknown writer named Tom Wolfe was dispatched to report on California’s cult-like surf scene for the New York Herald Tribune. He wound up at Windansea Beach in La Jolla, right up the shore from my boyhood home. In an article that would be reprinted as the title piece of his 1968 essay collection The Pump House Gang, Wolfe described the carefree, narcissistic lifestyle of the “surferkinder” he encountered in the same way he might have described a lost tribe in the Amazon. 

My favorite beach was—and is—Torrey Pines, which takes its name from the trees that grow atop the bluffs behind it. Gnarled and twisted by the wind and rich with dark-green needles, Torrey pines are like full-size bonsai. And this particular spot is one of only two places on the planet where they grow.

When I moved back to San Diego in 1995, I wound up living just five minutes up the road from Torrey Pines. And when I decided to take up boogie boarding again last summer, it was there that I hit the waves. What struck me more than anything as I paddled away from the beach was that it felt, smelled, and even looked exactly the same as in the good old days. 

I’d even venture to say that Torrey Pines, which has been protected as a state park for more than a century, pretty much looks as it did when the first Spanish settlers arrived 250 years ago. And that’s maybe what I love most about San Diego: despite its evolution into a cosmopolitan 21st-century city, the past is never too far away. 

 THE DETAILS 

Getting there

From Singapore and Hong Kong, United Airlines operates daily flights to San Diego via San Francisco. 

Where to Stay

Located in the historic Gaslamp Quarter, Pendry San Diego (1-619/738-7000; doubles from US$315) is one of the town’s most stylish hotels. For old-time flavor, The Cosmopolitan (1-619/297-1874; doubles from US$110) in Old Town features Victorian-flavored guest rooms, an outdoor bar, and a Mexican restaurant. 

Where to Eat and Drink

Unpretentious French nouvelle cuisine is the draw at Carlsbad’s Jeune et Jolie (1-760/637-5266), while Il Dandy (1-619/310-5669) in Bankers Hill puts the focus on contemporary Calabrian-influenced Italian. But you’ll want to seek out the city’s Mexican food too. Try any of the Lucha Libre outlets for top-notch tacos, or go old-school in Barrio Logan at Las Cuatro Milpas before hitting nearby Border X Brewing (1-619/501-0503) for some Mexican craft beer. In Old Town, there’s also an excellent Oaxacan-leaning menu at Tahona (1-619/255-2090), though the main draw here is over 120 kinds of mezcals.

What to Do

From visits to the Maritime Museum of San Diego to walking tours with the Gaslamp Quarter Historical Foundation & Museum, there’s plenty to keep one busy around town. A must-see on the cultural front is Chicano Park, a mural-filled monument to the city’s Mexican-American heritage. For natural beauty, Torrey Pines State Natural Reserve affords hikes along rugged sandstone bluffs and beautiful views of the Pacific.

This article originally appeared in the December 2019/January 2020 print issue of DestinAsian magazine (“A San Diego State of Mind”).