Where to Go on a Date in San Diego This Winter
From speakeasies to trivia nights, beer festivals, and more, these date ideas are sure to impress.
Near-perfect weather and practically limitless activities ranging from entertainment to adventure are at the top of the list of reasons why we all love living in San Diego. We’ve got scores of beachside bars, an award-winning brewery scene, and plenty of picturesque hikes to remind us why it’s called America’s Finest City. But our wealth of options also makes planning date night especially challenging. To help you narrow down the selection, we’ve rounded up the very best the city has to offer, whether you’re looking for a casual hang, an impressive first date, or a grand celebration. Here are our favorite things to do and places to go with someone special this winter:
Kick back together at a tiki bar
Tiki culture never really left San Diego, so on those rare days when a romantic walk on the beach isn’t in the cards, fake it by sharing a tropical libation served in a cool tiki glass with one of those little paper umbrellas. Old school favorites Bali Hai, Kona Kai Resort and Spa, or Moray’s at the Catamaran Resort serve up classic (read: strong) Mai Tais, Zombies, and Scorpion Bowls, while new wave tiki bars like Mothership, False Idol, The Grass Skirt, and Forbidden Cove bring modern tiki interpretations that range from plush and fruity to refreshing and crisp.
Thursday, January 13–Sunday, January 16
Marriott Mission Valley
You and your beloved can take your first steps or learn advanced moves from the best at BIG Salsa Festival San Diego. The four-day event includes workshops, classes, live bands, dance performances, and open dancing every night until 4 am.
Reach your fitness goals together
Setting fitness goals together and working to achieve them brings you closer to your love, not to mention encouraging sweaty sessions of another sort. Keep your new year, new you resolutions and have fun doing it at one of the many road races that take place across the county every weekend. The Carlsbad Marathon, Half-marathon, Surf Sun Run 5K and the Double Down Challenge has a race length for everyone on a fast oceanfront course on Sunday, January 15, plus virtual options for all distances and a great swag bag. Kick off Super Bowl Sunday in February and make room for all those nachos you’re gonna eat at the Kook Run 5K and 10K in Encinitas, a gorgeous run along the I-101 that includes pro and elite divisions and a fun costume contest.
Visit a secret bar
Everybody loves to be in on a secret, even when it’s not really a secret. There’s just something vaguely clandestine (and a bit naughty) about going into, say, Kilowatt Brewing’s Oceanside tasting room and finding the hidden passageway, where a “space elevator” beams you up to the planet Rillispore and The Space Pad, a 1950s Atomic Era-style spaceport. Open a door at the back of Common Theory in Kearny Mesa to visit a futuristic Chinese apothecary, the stunning Realm of the 52 Remedies. Sneak behind the walk-in refrigerator in Craft & Commerce for tropical libations at False Idol, while Convoy Music Bar is accessed via the alley behind The Taco Stand (hint: look for the red light.) Reservations are usually required, so check the website before heading out.
Rock out to live music
Nothing beats seeing a live band, but tickets for the big names can get expensive. Fortunately, San Diego’s live music scene is as exciting and diverse as the venues that provide them. The Belly Up in Solana Beach welcomes acts ranging from Saharan folk music to alt-reggae, with a good sprinkling of legendary early rockers from the ‘60s and ‘70s. The Music Box’s three tiers of seating include opera booths with bottle service, two outdoor patios, bars on two levels, and a private VIP skybox overlooking the stage, as well as a menu that includes kobe sliders, charcuterie, flatbreads, and cocktails on tap. See up-and-coming underground alt-rock at the famously divey Casbah, where past guests have included Nirvana and Smashing Pumpkins, or hit Winston’s Beach Club in Ocean Beach for a jam band/reggae vibe.
Saturday, February 4
What’s more romantic than strolling through one of San Diego’s historic neighborhoods, enjoying all the best sips and bites from local restaurants, bars, and breweries? In February, explore all that Barrio Logan has to offer at Taste of Barrio Logan, a self-guided tour of one of San Diego’s culinary meccas, starting at Attitude Brewery and ending with an after party at upcycling distillery ReBru Spirits.
Thursday, February 9-Sunday, February 12
Tenth Avenue Arts Center
Go for the glory at GamerCon XII, with four full days on five different floors packed with gaming experiences. The first floor features more than 40 PCs and consoles in the PC Gaming Pit and Console Coliseum, as well as a Retrocade full of ‘80s and ‘90s arcade classics. Local San Diego- and SoCal-based artists and cosplayers fill the second floor Art Gallery, while roleplaying and miniatures gaming occupy Lich’s Tomb on the third floor. The fourth floor’s Dragon’s Hall holds new and classic board games, as well as the UnPub Tavern for beta testing new ideas and checking out up-and-coming games. Finally, relax over a craft beer or cocktail on the Rooftop Lounge, and check out the stage schedule for details on cosplay contests, workshops, demos, and live music performances. Ticket prices and information are expected to be posted soon.
Saturday, February 11
Put the legendary aphrodisiac powers of America’s favorite confection to the test at For The Love Of Chocolate—The Escondido Chocolate Festival. More than 20 restaurants, shops, and spas will be offering chocolate samples or a chocolate-themed dish paired with local craft beer, bubbly, and wines. Second Saturday Arts and Culture Experiences will be happening nearby, where you’ll find art galleries, interactive arts, theater, museums, and educational events throughout the area, all day long.
Unleash your nerdy side at trivia night
Intelligence is sexy as hell, and trivia nights are a great way to gauge whether your crush will still be as alluring tomorrow morning. Fortunately, you’ve got options for basically every night of the week. Belching Beaver in Oceanside pairs trivia with rotating food trucks on Mondays, Park & Rec in University Heights is a popular spot on Tuesday nights, The Regal Beagle in Mission Hills has Wednesdays covered, and the East Village’s Knotty Barrel Gastropub combines trivia with half-price bottles of wine every Thursday night.
Spend a day wandering hand-in-hand at participating San Diego museums for half-price all month long in February, when you pick up a free Museum Month pass at one of 75 local libraries, Macy’s stores and Hilton Hotels. Your pass gets you up to four half-price admissions to more than 40 cultural institutions throughout San Diego County, including the new Comic Con Museum, the Birch Aquarium at Scripps, the San Diego Natural History Museum, and the San Diego Museum of Art. At the latter, you’ll find three outstanding exhibits: Chapel of the Rocks by Justin Sterling (through February 12, 2023), is an immersive experience of broken and mended stained-glass windows; Lisa Ross: Elegy to a Uyghur Homeland (through March 5, 2023) poignantly captures the rituals and spiritual traditions of Uyghur shrines and everyday life in and around the Taklamakan Desert captured during the artist’s decade-long travels through the area; and Sergio Hernandez: Embers of Oaxaca (through February 12, 2023), the first U.S. solo museum exhibition by Oaxacan contemporary artist Sergio Hernandez. It showcases more than 30 large-scale paintings and mixed-media works, some of which will debut to the public for the first time as part of this exhibition.
Given our status as a craft beer capital, it’s inevitable that you and your love will find yourself bonding over saisons or sessions at a beer garden or festival. Mark your calendars for Saturday, January 7 as the 12th annual San Diego Brew Festival returns to Liberty Station for a fun-filled day with unlimited tastings from over 70 craft and international breweries, live music, and some of San Diego’s most popular food trucks. Later in the month, head to Pure Project’s 7th Anniversary Party, where they’ll turn part of their parking lot into a beer garden with tents, food trucks, music, games, rare and specialty beer tappings, and a cellar bottle sale.
Introduce each other to the agave spectrum at Cantina Mayahuel, where over 100 different mezcals, sotols, bacanoras, and raicillas line the wall behind the bar. While mezcal margaritas are available (and delicious), aficionados prefer to sip it neat, and the friendly, knowledgeable bartenders will gladly guide you through your tasting experience. If mezcal isn’t your thing, there are also 250+ varieties of tequila, including the house brand, Don Lorenzo Reposado Reserva. Their expanded patio can accommodate in-house drinking and dining on a first-come basis.
Explore Balboa Park like a tourist
Not unlike human relationships, it’s easy to start taking even a treasure like Balboa Park for granted. Renew your love for both with a romantic hand-in-hand stroll through the exquisite gardens and architecture, hike one of the 19 trails, or snuggle through a free afternoon concert at Spreckels Organ Pavilion, held every Sunday at 2 pm.
Check out a food hall
Food halls, the latest trend in casual dining, are a far cry from the old mall food courts you used to hang at back in middle school, plus you can scope out your new crush’s culinary leanings while indulging your own whims. The Sky Deck at Del Mar Highlands Town Center, Market on 8th in National City, the Liberty Public Market in Liberty Station, and the Old Town Urban Market in Old Town host craft cocktail bars and nearly every kind of food shop you can imagine, from pizza to poke.