Vast and varied, San Diego County comes with an impressive skyline, desert landscapes, scenic hikes and coastal views to rival Big Sur. A boardriders paradise, this southern corner of California has 175 miles of surf-able coastline and dozens of neighborhoods – all with their own personalities, laid-back locals and perfect weather. It’s literally always 70-something degrees, at any time of year.
Craft beer and Mexican food is not just an experience in San Diego, it’s a lifestyle. And don’t worry if you forget your party frock you won’t be turned away for wearing flip flops, boardies or leggings almost anywhere. Spend your days immersed in farmers’ markets and floral gardens, go on a whale watching boat trip or learn something at one of some of the city's 90+ museums. There's even an enormous inland city lagoon – perfect for paddle boarding and cycling around. San Diego has it all.
With miles of coastline, rugged mountains, craft beer and a unique food scene, San Diego is packed with opportunity for fun and adventure © David Toussaint / Getty Images
Million dollar properties sit on rolling hills and rugged cliff edges overlooking a long, wide sandy beach in San Diego’s fanciest neighborhood. One of La Jolla's (pronounced “La-hoi-ya”) most celebrated residents, Theodor Geisel, also known as Dr. Seuss, lived out his final years in a mountaintop retreat in this pretty, chilled-out neighborhood and it’s easy to see why.
The pleasant main streets around Girard Ave are affectionately named “the village” by locals who spend their time in designer boutiques, local art shops and dining at the fine seafood restaurants like George’s at the Cove. Out-of-towners gather at La Jolla Cove and the Children’s Pool to soak in the views and watch the resident seals and sea lion colonies.
La Jolla is packed with posh places to stay and eat, as well as outfitters to get you out on the water for some kayaking and animal viewing © Ron Thomas / Getty Images
Kayaking is another big attraction and an opportunity to get up close to the inquisitive sea mammals as they follow the colorful procession of boats along the coastline. When the seas are calm you can paddle right up to the famous Sunny Jim Sea Cave. An aging German painter and mining engineer had the cave dug by pick and shovel in 1902. He then charged a few cents to visitors who wanted to be lowered via ropes for the view. It is rumored that the cave was also used to smuggle contraband whiskey into San Diego during Prohibition.
The heart of San Diego’s beach culture, Pacific Beach or ‘PB’ as locals call it, is a palm tree-lined residential area favored by college students and surfers. Plenty of sports bars like 710 Beach Club and tiki bars like the Grass Skirt can be found around Garnet Street and Grand Ave, but the main attraction is the 3.2-mile boardwalk and beach lined with shops and bars that serve over-sized cocktails like the Baja Beach Cafe.
There’s a certain faded glory about the place. It’s not as smart as La Jolla to the north, but it’s certainly the best people watching spot in town. On any given day the boardwalk is full of skateboarders, cyclists and promenaders. During holidays the long sandy beach, which turns into Mission Beach at its southern end, is sprawling with families and buff Californians sunbathing, body boarding and playing frisbee and spike ball.
Pacific Beach boardwalk has miles of family fun © Richard Cummins / Getty Images
There are a couple of decent surf spots here too. Short boarders prefer the peaky break on the north side of Crystal Pier, while legendary longboarders like Skip Frye still ride waves at Tourmaline Surfing Park at the north of Pacific Beach.
South of Mission and Pacific Beach, but separated by a channel of water, Ocean Beach feels very different from San Diego’s other beach communities. A little slower paced, it’s home to artisans, yogis, vegetarians, hippies, alternatives and craft beer fans. Antique shops, organic cafes and psychedelic buildings line Newport Ave in the center of town. It’s easy to spend an afternoon rummaging through second-hand records and collector’s comics or perusing the fresh goods at the Wednesday farmers’ market.
Don’t expect a fancy dining experience though, the laid-back tattoo-clad locals are proud of their ‘hood’s casual, almost scruffy feel. Entertainment comes in the form of dive bars, microbreweries and affordable, independent burger (Hodads) and taco joints (South Beach Bar & Grille).
Activities include romantic walks at Sunset Cliffs Natural Park for dramatic cliff formations and weird caves, or fishing off Ocean Beach Pier, and exploring tide pools. Plus, you can let Fido run wild at the leash-free Dog Beach to the north.
Gas Lamp Quarter
This buzzy district is the main ‘going out’ spot in San Diego with flashy, pricey bars and restaurants targeted towards a touristy crowd. Look above the packed restaurants and upmarket hotels occupying street level for remnants of the area’s fascinating past.
Originally developed in the 1860s, the Gas Lamp Quarter is recognizable by it’s old-style ‘gas lamps’ and intricate Victorian buildings dotted around the area’s 16 blocks. Standout designs include the 1888 Louis Bank of Commerce building with ornate balconies and a Baroque revival-style facade topped by twin towers – the building was once the Golden Poppy Hotel, a brothel run by fortune-teller Madame Cora. The Yuma Building is also shrouded in legend. It was formerly owned by Captain Wilcox, who arrived in 1849 in command of a 120-ton sailing ship named the Invincible. Inside the clapboard-style William Heath Davis House built in 1850, you’ll find The Gaslamp Museum and more information about the landmarks of the area.
Look up while strolling through the Gas Lamp District and enjoy the Victorian details in this historic neighborhood © Meinzahn / Getty Images
A few minutes walk east is one of San Diego’s emerging hipster neighborhoods, East Village, with some surprisingly good restaurants. The French-style bistro Chloe and hidden speakeasy Nobel Experiment, decorated with golden skulls, are just a couple of stand-out offerings. A stroll to the west brings you to Embarcadero – a harbor including the USS Midway Museum (a giant Navy aircraft carrier you go inside) and a collection of historic tall ships at the Maritime Museum of San Diego, (including the oldest active ship – the 150-year-old Star of India). Scenic ferry rides across the bay to Coronado island also depart from here.
The heart of San Diego’s LGBTQ scene is the most diverse neighborhood in San Diego. Local business owners proudly fly rainbow flags over their vintage clothing shops, alternative bookstores and coffee houses while the Landmark Cinema screens independent foreign films.
During the annual summer Pride Festival, Hillcrest’s streets throb with glitter-dowsed revelers, but people from all ethnicities meet in Hillcrest year round. Prejudice-free ‘safe spaces’ include the country’s only openly gay brewery (Hillcrest Brewing Company), and clubs and bars like Gossip Grill and Flicks along University Ave – hosting DJs, drag shows, and karaoke.
Meanwhile, Hillcrest’s varied restaurant scene has flavors from Lebanon to Vietnam at lower prices than the touristy Gas Lamp District. Two miles east of Hillcrest is North Park, San Diego’s hippest neighborhood, with trendy thrift shops and retro bars – Coin-Op has dozens of vintage arcade games, and Polite Provisions is a smart apothecary and old soda shop-style bar.
The ultimate date night neighborhood, easily walkable Little Italy is a cluster of great Italian restaurants, and so much more. Sitting between San Diego’s International Airport to the north and Gas Lamp District to the south, it’s a surprisingly laid-back spot in the center of the city in which to grab a bite at patio cafés, urban breweries, wineries and authentic Italian restaurants like Filippi's Pizza Grotto – hidden inside a traditional Italian deli.
Enjoy a charming date night in San Diego's Little Italy © Richard Cummins / Getty Images
It’s also the place to sign up for cooking classes with an Italian chef (or grandmother) or do a pizza tasting tour. Amici Park is a chilled out area to take in neighborhood life and watch people playing bocce (the Italian version of French boules or British bowls) and the park’s amphitheater screens European movies during the Little Italy Summer Film Festival.
San Diego residents are very proud of their giant green space in the middle of the city. The 1,200-acre park is a mile and half from Gas Lamp District and includes 17 museums, including the San Diego Air & Space Museum, the San Diego Museum of Art, San Diego Natural History Museum and the famous San Diego Zoo – with more than 3,700 animals including polar bear, panda, and elephant enclosures.
Beautifully detailed Spanish Colonial Revival architecture, built for the 1915-16 Panama–California Exposition, sits at the park’s center. On Sundays, rain or shine, the largest outdoor organ in the world opens its shutters for a live concert.
Horticulturists can peruse 350 species of flora around the park (plus 1,500 trees) or visit the free Botanical Building with more than 2,100 plants and the exotic Japanese Friendship Garden with cherry blossom trees, bonsai exhibition, azaleas, camellias and magnolias.
This kitsch ‘little Mexico’ is a bizarre experience, but terribly fun. It’s stacked with souvenir shops selling brightly colored Day of the Dead skulls, sombreros and Mexican blankets. Yes, there are mariachi bands, salty Margaritas on tap and truckloads of tacos (we recommend the freshly made ones at Old Town Mexican Cafe), but there are notable historic sights too.
Kitschy and delightful, a day in Old Town reminds visitors of San Diego's Hispanic heritage © Julie Thurston / Getty Images
More than 30 preserved buildings sit in and around Old Town State Park, including the former home of a Spanish aristocrat Casa de Estudillo, constructed in 1827, plus a reconstruction of the Alvarado House – the former home to the sister of the last California governor appointed by Mexico, originally built 1824.
Constantly named one of the best surfing towns in the world, wave riders move here from across the globe to be close to the first class surf break Swami’s – honored in the song Surfin’ USA, by The Beach Boys. Encinitas sits around 20 miles north of San Diego’s city limits on the historic Highway 101 and is littered with traditional diners, cafes (including the tasty Swami’s Cafe) and surf shops.
Moonlight Beach in Encinitas is perfect for playing in the waves and evening beach fires © Doug Berry/Getty Images
Catch a surfing film or cult movie at Encinitas’ retro 1928 movie theater La Paloma, one of the first places to show ‘Talkies’ (fun fact: Mary Pickford attended the opening gala). Classic Car Nights are a big thing in Encinitas too. Hot rods congregate on Main Street as ’50s and ’60s bands play on the third Thursday of each month (between May and September). Meanwhile, the free Self Realization Fellowship Hermitage & Meditation Gardens, overlooking Swami’s surf break, attracts folks practicing meditation and yoga.
Families enjoy the large, flat Moonlight State Beach for its volleyball and tennis courts and fire pits – it’s one of the few places you can still have sunset bonfires and barbecues. If all that fails, the epic Legoland amusement park is only 15 minutes drive north.
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