19 Great San Diego Dates to Go on This Fall

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 fall:

Walk the red carpet at a film fest

Various locations
Upgrade your dinner and a movie date night at the 20th Annual San Diego International Film Festival running from October 14–24, with world-premiere films, never-before-seen studio releases, new and unique independent filmmaking, as well as elegant parties and meet-and-greet events with the filmmakers, available in-person or virtually. The 22nd Annual San Diego Asian Film Festival returns from October 28–November 6, offering the largest exhibition of Asian cinema in the western United States, featuring west coast, North American, and world premieres of global films.

Leave the trick-or-treating to the kids

Various locations
San Diegans of all ages love Halloween, and there’s no shortage of places to go and parties to attend. A quick online search will turn up dozens of events, including the return of the Haunted Trail at Balboa Park from September 24 through Halloween night; San Diego’s most famous haunted hotel, the Hotel del Coronado, has a full slate of spooky fun planned; and Estancia La Jolla Hotel and Spa hosts their inaugural Bridgerton Masquerade Halloween Soirée on Halloween night.

San Diego Bayfest
San Diego Bayfest

Dance till you drop at a music festival

Various locations
Nothing brings two (or a few thousand) people together like watching a favorite band perform live, and music festivals are a great way to get to know your new crush. While the fate of KAABOO hasn’t been decided yet for 2021, there are plenty of other opportunities for open air concerts and festivals. Hit San Diego Bayfest in July for an all-reggae lineup that includes ten bands, all appearing on one stage, so you don’t waste time running between stages to see your fave acs. San Diego’s favorite electronic music festival returns in August when CRSSD Festival takes over Waterfront Park for two days from noon to midnight, with three stages of world-renowned DJs guaranteed to get you dancing. November’s Wonderfront Music and Arts Festival has multiple venues spanning the entire waterfront from the Broadway Port Pier to Embarcadero Park South with the added convenience of a RFID wristband that allow fast and easy access between stages, as well as the option to explore the more than 250 neighboring restaurants, bars, and breweries.

Guzzle all the brews

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. Put chocolate’s reputation as an aphrodisiac to the test in June when Thorn Brewing Co joins Sideyard BBQ by HottMess, ReBru Spirits, and Kové Hard Yerba Mate in creating special chocolate offerings inspired by the tasty bars from Chuao Chocolatier. Mark your calendars in July for Duck Foot Brewing Company’s 6th anniversary with their 6th Anniversary Triple IPA, barrel aged beers, sours and more, plus awesome food trucks and live music in their Miramar Brewery’s outdoor space. Hit Belmont Park in August for BeerX, a full day of beer, music, and food at the beach.

Pacific Beachfest
Pacific Beachfest

Hit the beach

Various locations
As if going to the beach isn’t fun enough, there’s always something cool going on there. In August, head to the Oceanside Pier to cheer on 350-400 world class bodysurfers from all over the globe as they compete for trophies and prizes at the Annual World Bodysurfing Championships. September brings Supergirl Surf Pro, the world’s biggest women’s surf event and festival, with more than 100 top women surfers competing for the $10K cash prize and the coveted Supergirl cape. Pacific Beachfest in October starts early with a pro volleyball tournament, surf competition, and 5K race followed by live music on three different stages, a Best of the Beach Fish Taco Contest, the Big Josh Beer Garden with local craft beers, sunset yoga, and vendor booths.

Lemon Festival | Third Avenue Village Association

Feast on the best local foods

Various locations
What’s more romantic than strolling hand-in-hand through one of San Diego’s unique neighborhoods, noshing on all the best sips and bites from local restaurants? If you’ve ever wanted to sample every restaurant in North Park, October’s Taste of North Park fulfills your wishes. Three different ticket options are available for beer tasting only, food tasting only, or both beer and food, so you can browse the neighborhood shops and wander the streets savoring bites and brews. Tacos are a whole food group in San Diego, so head to Waterfront Park in mid-October for SoCal Taco Fest 2021, with a full slate of live music, taco tastings, lucha libre matches, Chihuahua races, and beauty pageants. The San Diego Bay Wine & Food Festival returns in November for the largest culinary and wine gathering on the West Coast, including signature events like The Grand Decant, the star-studded Grand Tasting, and the ultimate taco throwdown, Taco TKO, where San Diego’s top chefs compete for cash, prizes, and bragging rights.

Ogle some art

Various locations
Whether your date takes you to Barrio Logan, Balboa Park, Hillcrest, Liberty Station, or almost any other neighborhood, wandering through local art galleries and museums is a must-do for any art lover. Stroll down beautiful Girard Avenue in La Jolla at October’s 10th Annual La Jolla Art and Wine Festival, hosting 150 artists from San Diego and beyond, plus a silent auction, live entertainment, pet adoptions, a gourmet marketplace, and a wine and beer garden. The art exhibits are free, but you’ll want to purchase tickets for the wine and beer garden (21+) in advance since capacity is limited.

See a movie on a rooftop...

Mission Hills
Every Thursday through Saturday the Mission Hills rooftop theatre, 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 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

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

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

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

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

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 

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

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 

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

Embark on a dinner cruise under a glowing moon

Little Italy
What could be more romantic than viewing San Diego’s glittering skyline from the water, beneath a luminous moon? Board Hornblower 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, or during the summer months, you might get a glimpse of blue whales, the largest animal on earth!

Pick up pickleball 

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 

La Jolla Shores
As the weather gets warmer, 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 

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 

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

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. Little Italy’s Food Hall at the Piazza della Famiglia, 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.