Why San Diego is (at Least) Six Vacations in One
To those who’ve never experienced San Diego—and even to some who have—it’s the ultimate SoCal beach city, whose 70 miles of prime coastline tell you all you need to know about the place (in a nutshell: sun, surf and serious Endless Summer vibes). And no one’s saying those aren’t totally worthy getaway goals, because even if you did nothing more there than park yourself on any of the iconic local beaches, the vacation would inevitably go down as one of your best. But, the city packs so many bonus escapes—thanks to a whole series of world-unto-themselves neighborhoods—we can’t let you miss out.
Granted, you've probably heard of some of these neighborhoods before, and you may well have spent time in a few. But even the oldest among them have new offerings you won’t want to deprive yourself of—particularly when said offerings are the kind you read off a menu. (Note that in a city that’s almost comically famous for its good weather, alfresco dining was a beloved way of life well before 2020 rolled around.)
So whether you’re thinking about your first visit to San Diego—or you’re a returning devotee—check out this guide to six of our favorite neighborhoods. Adding even one or two to the mix will make you feel like you’ve gotten a getaway-within-a-getaway. And rest assured, you'll still go home feeling like you've had a gloriously beachy escape.
To begin at the beginning, as it were, make Old Town your first stop. The scene of the first permanent European settlement in California, this neighborhood dates back to the late 1700s—and much further if you consider the 9000+ years of Kumeyaay history that preceded both the Spaniards and the 19th-century Mexican settlers along the banks of the San Diego River. In fact, to bring those millennia of indigenous history into sharper focus, the Old Town State Historic Park is debuting a long-anticipated Land of the First People Educational Park—or Iipay-Tipai Kumeyaay Mut Niihepok—this spring.
And in light of how much else there is to see, do and eat in the neighborhood, you’ll want to give yourselves at least half a day here—especially if you’ve got kids in tow, and you visit on a Wednesday or Saturday, when the Old Town San Diego State Historic Park stages fun demos by period-costumed blacksmiths and others. Kids will also love the resident donkeys, the vintage toys that adorn the children’s bedrooms at the 200-year-old Casa de Estudillo (all visible from the courtyard though large, open windows) and the creaky, old windmill (one of the only working windmills in any U.S. state park).
Also within the bounds of the State Historic Park: Fiesta de Reyes Plaza, where you’ll find the mostly alfresco Casa de Reyes Mexican restaurant, an outdoor stage, and countless specialty shops (peer into The Tile Shop, at a minimum). But whatever you eat or drink there, you’ll want to save room because just beyond the park’s borders, streets-full of amazing offerings beckon. In fact, at the restaurants that line San Diego Avenue, beloved “tortilla ladies” make fresh corn and flour rounds before your eyes (not that you’d need visual proof—the scent is a dead giveaway), and you should buy half a dozen to go even if you’re not planning to sit down for a meal. Something else you should pick up to snack on as you wander Old Town’s streets: the absurdly good Oreo Churros at the Wave-Caffe Vergnano.
Duly fortified, you’ll be set to wander the rest of the neighborhood. Highlights include the historic Campo Santo Cemetery and the nearby Heritage Park Row, a series of beautifully restored Victorian homes alongside San Diego’s first synagogue. To cap off your tour of the area—at least if you’re traveling sans kiddos—check out one of the best new additions: Tahona, home to an impressive array of mezcals and delicious Oaxacan fare to pair them with. And like most local establishments, Tahona has ample outdoor seating.
To view local history through more of a maritime lens—and have plenty of timeless fun in the process—head to this neighborhood that runs along San Diego Bay. Though vessels of all kinds float just offshore, arguably the most famous is the USS Midway—the longest serving aircraft carrier of the 20th century, and now an endlessly fascinating museum (among the new health precautions: online ticket purchase and timed entry). Another beloved historic ship along the Embarcadero is the 19th-century iron-hulled, full-rigged Star of India—one of several vessels that make up the Maritime Museum of San Diego, and that have opened with precautions in place.
After the excitement of historic ship exploration, head to Seaport Village, a charmingly old-timey collection of shops, restaurants, bars and attractions. The newest, which craft beer lovers won’t want to miss, comes courtesy of the locally revered Mike Hess Brewing, whose latest outpost is complete with bay views to rival the menu. (If wine is more your thing, know that San Pasqual Winery operates an adorable tasting room with outdoor seating on the same stunning stretch of waterfront.)
There are countless family-friendly spots in Seaport Village, but whether or not you’re traveling with kids, check out the offerings at the Kite Flite Shop. As you’ll gather in the neighboring Embarcadero Marina Park, famously favorable winds draw kite enthusiasts of all ages to this gorgeous, grassy expanse. Whether you join in the fun, or simply take it all in, the rainbow-colored kites with the bay for a backdrop make for a dreamy retreat.
Keep the serenity going with a walk along the water, where the views—all yachts and seabirds and rippling sapphire waves—make this path a favorite among bikers and runners, too.
For a completely different take on life by the water, head to a neighborhood where surfboard signage adorns every other storefront, wetsuits pass for streetwear and vintage Vans (whether of the footwear or VW variety) reign supreme. Yes, we’re talking about Ocean Beach—that’s OB to locals—where you can’t get more classic than the local surf vibes.
To get an immediate (and gorgeous) sense of the scene, head straight to the Ocean Beach Pier, best known as the longest concrete pier on the West Coast, but equally notable as a backdrop: Check out the water below the supports, almost invariably, you’ll see a whole lineup of surfers—some catching waves, others waiting on the next one.
From there, make your way back inland a bit along Newport Avenue. Grab a burger—any burger—at the fabled Hodad’s (where even the outdoor seating area is demarcated by a fence of standing surfboards), and don’t forget the onion rings. Then peruse the local businesses, whether the vinyl collection at Cow Records, the surfwear at South Coast Wahines—or just the eye-popping façade of the street’s famed former hostel.
But wherever your OB wandering takes you (and if you’ve got a four-legged friend along, that should include the beloved Dog Beach), you’ll want to be back at one specific place by late afternoon: the aptly named Sunset Cliffs Natural Park. Alternately, if you prefer a sundowner with your sunset, snag a seat outside at the ocean-facing Surf Lodge and order the Mai Tai—the best in town, according to many a local.
One of the city’s coolest neighborhoods, Barrio Logan is best known as the home of Chicano Park—the art-filled, 8-acre enclave beneath the San Diego-Coronado Bridge—and the surrounding blend of culture, heritage and creativity.
Having just celebrated its 50th birthday in 2020—and having been declared a National Historic Landmark three years before that—Chicano Park remains the cultural heart of the historically Mexican-American neighborhood, and the best place for visitors to start. More than just an eye feast, the art adorning the bridge pillars throughout the park serves as a visual history of the community, to the point that you’ll want to have a mural map on hand.
In fact, given the sheer quantity—reportedly the largest collection of outdoor murals in the U.S.—you may want to do some advanced research so you can zero in on the works of greatest personal interest (whether Latinx icons, indigenous deities or other locally resonant symbols, all of these portrayals tie back to themes of social justice and Chicano history).
Once you’ve had your fill of public art, fill up on some of the other things the neighborhood is famous for. Don’t miss Salud, whose Papa Fried Shell tacos (think mashed potato tacos) taste divinely inspired—as do the blended coffee drinks at Por Vida (try the horchata latte). And if craft beer is your beverage of choice, good news: The already thriving local brewery scene has welcomed an instantly beloved newcomer. The Latina-founded Mujeres Brew House serves up Buenas Vibras (a grapefruit-infused blond ale), La Jefita (a tamarind Hefeweizen), and all manner of deliciousness in between.
As you’re walking everything off, stop by some of the great local shops. One new favorite is El Puesto SD, owned by two sisters—one of whom is the resident huarache curator (and for that reason alone, the store is worth a visit), while the other maintains an expertly edited vintage collection.
Thanks to waves of Sicilian and Ligurian immigrants who began building up San Diego’s tuna fishing industry in the 19th century, Italian culture figures prominently into the local mix, too. And as you might guess, Little Italy is the best place to find the vestiges. But as you might not guess, it’s also one of the best places to go for ground-breaking, news-making cuisine—plus some of the chicest décor and design shops in town.
For a quick historic overview, check out a few of the longstanding fixtures—from Our Lady of the Rosary Catholic Church (the nearly century-old spiritual heart of the neighborhood) to the Waterfront Bar and Grill (said to be the city’s oldest continually operating tavern, where Italian fishermen would relax after mending their nets outside the front door) to Mona Lisa Italian Foods (the old-school, family-run deli and restaurant whose sandwiches and slices are legendary).
You’ll also want to check out a few modern nods to the neighborhood’s Italian heritage: Piazza della Famiglia (a 10,000-square-foot plaza where you can enjoy takeout treats from the new Little Italy Food Hall), the more intimately scaled Piazza Basilone (a tribute to WWII Medal of Honor Recipient Gunnery Sergeant John Basilone); and—on Saturdays—the Little Italy Mercato (a vibrant, open-air market).
But you’ve got to show up prepared for at least two meals: ideally, an old-school Italian lunch, followed by a long promenade—this would be the time to work in a visit to the chic Kettner Arts & Design District—and topped off with dinner at one of the city’s buzziest modern restaurants. These include Juniper & Ivy, Herb & Wood, Ironside Fish & Oyster (noticing a theme?).
In keeping with the alfresco theme (because every restaurant we’ve mentioned offers some version of it), wine lovers should make time to pull up a seat outside M Winehouse—a beloved wine bar that occupies the neighborhood’s oldest house: a tiny Victorian beauty that dates to 1888, and makes for the perfect place to toast to your neighborhood discoveries.
For sheer natural beauty, you can’t do better than the Edenic enclave that curves around—and periodically rises above—the Pacific for seven stunning miles. Arguably the best place to start is downtown La Jolla, whose stretch of coastline includes the fabled Cove and Children’s Pool.
The latter, for the uninitiated, isn’t actually a pool: It’s a tiny protected beach that has become home to an impressive population of seals and sealions. Because of the pupping season in progress, you can’t go down onto the beach itself until mid-May. But you can still walk out onto the skinny breakwater that curves around the front of the beach, where you’ll be hemmed in by some of the planet’s most beautiful water. On a clear and sunny day (i.e., often), this patch of the Pacific goes totally glassy, so you’ll see not only the emerald-color kelp forests, but also whatever’s frolicking among them. And during pupping season, that’s a lot of baby seals. From the breakwater, you have an equally amazing view of the babies on the beach, along with their mothers.
You’ll try to process what you’ve just experienced as you make your way back up to the main drag through the Ellen Browning Scripps Park, but the walk is too short to integrate so much mind-blowing nature. So you’ll have to stroll and snack your way through the area, stopping at such icons as Warwick’s books and Sugar & Scribe bakery, as you regain your bearings.
From here, you can make your way to La Jolla’s even wilder stretches of coastline—all the way up to Torrey Pines State Natural Reserve.
Wherever your wanderings take you, you’ll want to be well positioned for sunset—and you’ll find some of the best sundowner spots back downtown. Consider George’s at the Cove, whose open-air rooftop Ocean Terrace opens for dinner at 4pm (try to reserve a rail-side table and arrive a few minutes early) or La Valencia’s outdoor tables, where—for a real neighborhood experience—you should order the regulars’ favorite secret menu item: a Kahlua, brandy and ice cream cocktail known as the Whaler.