21 Awesome Winter Date Ideas in San Diego

Get back out there.

Near-perfect weather and an abundance of entertaining and adventurous activities are at the top of the list of reasons to love living in San Diego, but it also makes planning date night especially challenging. How do you pick just one when there are so many choices? To help your nervous heart beat a bit more slowly, we’ve narrowed it down to 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:

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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, January 14-17. The four-day event includes workshops, classes, live bands, dance performances and open dancing every night until 4am. Friday features a midnight concert by popular salsa romántica singer José Alberto “El Canario”.
Cost: Full passes are $200 through January 1, when they will increase to $225. Full passes will be $300 at the door.

Reach your fitness goals together

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Various locations
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 January 19, plus virtual options 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 101 that includes pro and elite divisions and a fun costume contest.

San Diego Museum of Art
San Diego Museum of Art

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Various locations
Visit participating San Diego museums in February for half-price all month long 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 in locations county-wide, including the USS Midway, the Birch Aquarium at Scripps, the San Diego Natural History Museum, and the San Diego Museum of Art.

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Tenth Avenue Arts Center
Go for the glory at GamerCon XI on February 3 through February 6, 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 information is expected to be posted soon.

Walk the red carpet at a film fest

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Various locations
Upgrade your dinner and a movie date night at the 19th Annual San Diego Black Film Festival running from January 26-30 at Theatre Box, with more than 100 films, including music videos, feature films, shorts, foreign/African Diaspora, GLBT, horror, and more. It’s also one of the most affordable events of its kind, with single-film tickets priced as low as $5. The Media Arts Center San Diego is celebrating the 29th annual San Diego Latino Film Festival from March 10-20, occupying five screens and presenting 175+ films from Latin America, the United States, and Spain. There'll also be parties on opening night (and closing night), Q&A sessions with visiting filmmakers, and free student outreach screenings, with audiences having the rare opportunity to meet filmmakers and actors from all over the world.

San Diego Brew Fest
San Diego Brew Fest

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Various locations
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 January 8 as the 11th 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 6th anniversary, where they’ll turn part of their parking lot into a beer garden with beer tents, food trucks, music, games, rare and specialty beer tappings, and a cellar bottle sale.

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Mission Hills
Every Saturday and Sunday the Mission Hills rooftop theater, Cinema Under the Stars, features the best classic and cult films, shown on a 20-foot screen with HD projection and surround sound. You can choose from safely distant single or double zero gravity recliners, loveseat cabanas or deck chairs with ottomans when you make your reservation online. The smallish snack bar serves coffee, tea, soda, bottled water, popcorn and a variety of candy for just $2 each. Come with cash—your credit card just reserves your seat online and they only accept dollars at the door and the snack bar for payment.

...Or at an old school drive-in theatre

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South Bay

Built during the heyday of drive-ins in 1953, South Bay Drive-in Theatre has undergone several renovations, finally upgrading to fully digital picture and sound, with the brightest picture quality available on three 100-foot screens. You can see a double-feature every day, year round for the bargain price of $10 for adults and just $1 for kids between five and nine years old. The snack bar covers all your movie faves, plus burritos, tacos and tortas, and they even have email coupons for food discounts, but feel free to bring your own goodies if you prefer. Audio is played through your car speakers, but if you’re concerned about your car’s battery life, bring along an FM radio—most audio apps don’t work well here. Plastic is accepted for tickets, but the snack bar is cash only.

Morley Field Disc Golf Course
Morley Field Disc Golf Course

Try your hand at disc golf

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Balboa Park
It won’t matter if you have beginner’s luck or flame out spectacularly, this mashup sport of golf and frisbee is still a good time at a budget-friendly price. Even on weekends, Morley Field Disc Golf Course’s surprisingly challenging 19 holes are a mere $5-$6. Afterwards, hit up Panama 66 for grab-and-go bowls, salads and ficelle sandwiches, and have an impromptu picnic in the park.

AxeVentures (San Diego)
AxeVentures (San Diego)

Unleash your inner lumberjack

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North Park, Oceanside
Yoga and meditation are great stress relievers, but so is throwing a tomahawk across the room, albeit it’s a little more...aggressive. Try your hand at AxeVentures, one of several tomahawk axe throwing venues that have popped up across the city. Book a lane online or walk in anytime, learn the ropes from one of the coaches, and spend the next hour or so perfecting your technique. Check them out on Thursdays in North Park and Mondays and Thursdays in Oceanside for Dark Light Night and one-of-a-kind date night memories. Safety note: Closed toe shoes, social distancing, and masks are required.

Climb the walls

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Grantville
Show off your climbing skills on 7,000 square feet of wall space at Grotto Climbing and Yoga. Featuring state-of-the-art indoor bouldering terrain, including more than 13,000 handmade holds, a campus board, a peg board, an illuminated moon board, fingerboards, and a 60-degree training board, climbers of all skill levels are ensured an exhilarating experience. In addition, there’s a yoga studio teaching all-level vinyasa, acroyoga, yin, restorative and Budokon-inspired flow classes, and a fitness area with a Rogue fitness rack, weights, and rings. The Intro to Bouldering class is a great choice for first timers and includes shoe rental, 30 minutes of instruction, and a day pass, so afterwards you can hit the weights or stretch out any sore muscles in a yoga class.

Bike along the Silver Strand

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Coronado Ferry Landing
The Silver Strand Bikeway begins at Coronado Ferry Landing, and takes you along the nine-mile flat, sandy tombolo all the way to Imperial Beach. Perfect for riders of all levels, you’ll be treated to views of the Pacific Ocean on one side and the San Diego Bay National Wildlife Refuge on the other. Don’t miss a stop at Silver Strand Beach for a quick swim or a walk along the sand. Your bike rides for free when you cross over on the ferry and rentals are available at the ferry landing if you haven’t brought your own.

Sip some mezcal at Cantina Mayahuel

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University Heights
Introduce yourselves to tequila’s sexier, smokier cousin 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.

Hammond's Gourmet Ice Cream
Hammond's Gourmet Ice Cream

Share an ice cream flight at Hammond's Gourmet Ice Cream

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Pacific Beach, North Park, Point Loma
Hammond’s Gourmet Ice Cream offers over 300 flavors of Tropical Dreams super premium Hawaiian ice cream and sorbet, which is the perfect excuse to skip dinner and go straight for indulgence. Having a hard time deciding between chocolate coconut macadamia nut, passionfruit sorbet, or peanut butter and guava jelly? Opt for flights of your favorites in adorable mini cake or waffle cones, to share (or not).

Drink wine and paint a masterpiece

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Liberty Station
Anyone can be an artist at Pinot’s Palette in the beautiful Liberty Station Arts District. Each 90 minute to two-hour session takes you through the creation of your own colorful painting, no experience required. Classes are held indoors and outdoors, with Pinot’s Palette bar service and a special menu from the neighboring Solare Ristorante available. Grab a glass of vino to get your creative juices flowing, then relax and follow the instructor-led, step-by-step directions. Whether you end up with flawless masterpieces or undisplayable accidents, it’ll certainly bring you closer.

Hornblower Cruises & Events San Diego
Hornblower Cruises & Events San Diego

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Little Italy
What could be more romantic than viewing San Diego’s glittering skyline from the water, beneath a luminous moon? Board City Cruises’ signature dinner cruises and enjoy a variety of different date night options, from cocktails at sunset to a three-course lobster dinner. There’s even a dinner and movie cruise featuring old and new classics. If you and your crush are more into daytime adventures, there’s sea life and whale watching cruises, where you can see migrating gray whales, Minke whales, and pods of dolphins.

Pick up pickleball

Free
Various locations
Invented in 1965, pickleball is a fast-paced, easy-to-learn mash-up of tennis, ping-pong, and badminton, where players (singles or doubles) face off and whack a wiffle ball with a solid paddle across a low net on a small court to score points. Give it a try at one of the open play sessions at dozens of outdoor courts across San Diego County, where some have free clinics for beginners.

The Marine Room
The Marine Room

Swim with sharks

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La Jolla Shores
The shallow waters of La Jolla Shores attract scores of leopard sharks, especially around the front of the tennis club and The Marine Room Restaurant. There, during peak season, the sharks typically hang out in groups of hundreds in about four to five feet of water. Although seeing a five-foot-long shark can be intimidating, leopard sharks pose no danger; despite being carnivores, they never attack humans. Besides, these sharks draw snorkelers from all over the world and are used to seeing people gawking at them. Use your own equipment or rent from one of the local shops within walking distance of La Jolla Shores Beach.

Explore Balboa Park like a tourist

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Balboa Park
Similar to 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.

Perfect your double axel at the mall

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University City
Lace up your skates and hit the ice at UTC Ice Sports Center, located next to the food court inside Westfield UTC. Daily public skating sessions are available two-hour sessions, and include four hours of free parking with validation, so you and your love can glide to your heart’s content, then grab lunch or dinner at one of UTC’s 55 cafes, coffee shops, or fine dining restaurants. Rental skates are included, and helmets are available for a few bucks more.

Little Italy Food Hall
Little Italy Food Hall

Check out a food hall

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Various locations
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. Market on 8th in National City, the Liberty Public Market in Liberty Station, and Windmill Food Hall in Carlsbad host craft cocktail bars and nearly every kind of food shop you can imagine, from pizza to poke.

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Mary Beth Abate is a San Diego-based freelance writer by way of Chicago and Los Angeles. Her hobbies include yoga, pickling and fermenting stuff, reading cookbooks, and drinking fabulous gin. Keep up with her experiments @MaryBeth_Abate.