12 Dates of Christmas: Planning a Romantic Evening in San Diego
’Tis cuffing season, as the kids say—the time of year when the weather turns chilly, office parties begin to commence, singles everywhere start to crave companionship, or at least a partner to keep them company during the cold winter months, and everyone is more likely to agree to a second date. Grabbing a drink may have been fine for the first date, but your next date calls for a more unique idea. Fortunately, San Diego is filled with fun and romantic things to do! From San Diego tours to a harbor cruise to the most romantic dinner spots in town, we’ve got you covered on all the best date night ideas in San Diego!
1) Ice Skate on Coronado Beach
You can drive across the bridge to Coronado Island, or, for a more romantic dating experience, the Coronado Ferry will get you there in fifteen minutes. Once you arrive at the Coronado Ferry Landing, there are over twenty-five unique shops and restaurants, decorated with Christmas lights, for you and your date to explore.
The beachfront ice rink, open until 8 or 10 pm—depending on the evening, is a unique experience that will wow your date, give you both a stunning view of the Pacific Ocean, and is sure to put anyone in the mood for romance.
*Insider’s Tip: This year, you can even reserve your own rink-side lounge at Frostbite where you and your date can enjoy a roaring fire pit with full food, beverage, and hot cocoa service. There is never a lack of activities in Coronado!
2) Catch an Underground Jazz Show at a Classic Speakeasy
For many tourists and locals, Prohibition Lounge & Liquor Bar goes unnoticed, and with its intentionally covert existence, it’s no wonder. The bar is both figuratively and literally underground, the entrance is made to favor the front door of a law office, and during the day, you wouldn’t even notice the door among the other shops and offices downtown.
However, at night, the doorman will escort you downstairs and through the hallway to one of the most happenin’ lounges in San Diego, where you can drink specialty cocktails, lounge on cute little couches, and listen or cut a rug to jazz, blues, and classic Holiday jams under romantic lighting. The cozy, cuddle-able feel of this speakeasy is one of the reasons why this makes for a great date.
*If you like this place, some other live jazz, blues, and funk music honorable mentions in San Diego are Music Box, Dizzy’s, and the Mediterranean Jazz Supper Club.
3) Hop Aboard a Sunset Sail or Harbor Cruise
San Diego is one of the largest harbor towns in America, including sunsets that are some of the best in the world, which means that it’s not too difficult to find a boat departing around sunset on any given day of the week.
If you hesitate asking a local sailor to borrow their yacht for the evening, you can instead book a tour on one of the Hornblower and Flagship Ferries, some of the tall ships at the Maritime Museum of San Diego, or the Schooner America at Next Level Sailing.
Our personal favorite, the Schooner America (pictured), is the world’s most famous racing yacht, and the reason is simple: The original America put yachting on the map and is why the most famous trophy in sailing is called The America’s Cup.
Although America’s history is rife, she hasn’t lost her romantic je ne sais quoi. If you want a unique, beautiful and elegant atmosphere in the middle of beautiful, picturesque San Diego Bay surrounded by colorful sailboats, a stunning sky, and your wonderful date, this sail is the perfect choice for a location to spend the night.
4) Catch a Drive-In, Dive-In, or Rooftop Movie
In the age of Netflix, home theater systems, and recordable television, people rarely go to the drive-in movie for the audio/visuals. They go for the nostalgia and intimacy of it all. Little is more cozy and intimate than laughing, crying, and enjoying a movie in the privacy of your own car.
If audio/visuals are more your thing, opt for a movie atop a roof overlooking the city. Rooftop Cinema Club (pictured) maintain that “great films deserve great locations, and because outdoor cinema is about embracing the world around us, this makes for a great experience.”
This date is considerably more comfortable than a car because they use comfy deck chairs with adjustable seat heights and plenty of legroom. In fact, they have recently added Rooftop Love Seats with enough room for two people to snuggle on the rooftop.
If you’re wishing that it was still summer, or haven’t retired your swimsuit yet, The Pearl Hotel Wednesday Dive-In may be right for you. You can watch a movie from inside the outdoor pool which makes for a very unique date. This month, the movies include Elf, Home Alone, National Lampoon’s Christmas Vacation, and (of course) Die Hard. After, grab your date and track down the best ice cream in San Diego.
5) Picnic (& December Nights) at Balboa Park
Balboa Park may be one of the most romantic places in San Diego. The park itself stretches over 1200 acres of land and there are many quiet spots inside the park where you can enjoy a picnic without distraction.
If you’re planning on heading to December Nights with a date this year, you need to time this one just right, in order to beat the crowd (and what a crowd it is), but it’s definitely worth it.
The crowd doesn’t really arrive until after sundown. The trick is to arrive just before the sunset, or even before, so that you can get a good parking space. Take a small wine and cheese picnic to eat on the grass for a romantic dinner, or just visit one of the cafes or restaurants in the park.
After the dinner portion of your date, explore the festive Holiday happenings, watch the tree lighting, and visit the free museums before heading back to your car and beating the departure crowd as well. If you time it right, this can be one of the most romantic dates on the list.
6) Enjoy a “Broadway Show”
San Diego offers a plethora of performances, orchestras, musicals, concerts, and theatrical plays, especially around the Holiday season. From A Christmas Carol, to the Winter pops, the possibilities in Winter are just about endless.
If your date likes to sing, take them to see Jingle by the San Diego Gay Men’s Chorus at Balboa Theater or The Grinch at The Old Globe. If a quiet, cultured evening is more your date’s speed, one of the many playful Nutcracker showings or a spirited symphony at Copley Symphony Hall can be a good idea. Grab a happy hour cocktail at a trendy San Diego bar and then head over to catch a show!
For an exciting, and less traditional Holiday show, opt to see the rock opera Jesus Christ Superstar at La Jolla Playhouse before it leaves for Broadway in 2019. There is nothing quite like a Broadway show to distract you from that seasonal stress.
7) Take a Sunset (or Sunrise) Beach Hike
Lace up those hiking boots, pack some extra trail mix, and take a hike at The Razor Point (1.3 miles) or Guy Fleming Trail (0.7 miles) in Torrey Pines. Both trails offer gorgeous, picturesques views of the ocean. In the winter, you may spot Gray Whales, however, bottlenose dolphins can be seen throughout the year.
If you’re feeling a bit more romantic and adventurous, the Beach Trail (1.7 miles) is a bit steeper, but allows access to the beach which is a breathtaking, secluded area to picnic or just cuddle and watch the waves with your date. Make sure to bring a blanket, sweaters, and a bottle of wine to warm up both you and your date.
8) Take a Romantic Ride in a Hot Air Balloon
Break the bonds of gravity aboard a magical Hot Air Balloon in Northern San Diego and impress your date by showing them that you aren’t afraid to think outside the box. With stunning views of rolling hills, lush vineyards, ranches, and country estate rooftops, all in the course of an hour, a balloon ride makes for an exhilarating experience.
Bring along a camera, or have your phone handy to snap a shot of the top of the balloon as it inflates. It will end up far above you. You’ll be amazed as your aerostat (fancy name for balloon) inflates from a canvas bag into a vibrant and colorful teardrop shaped vessel.
Check with your pilot beforehand to see what you and your date are able to bring along with you on this adventurous ride above the city.
9) Browse the Shops and Learn to Salsa at Seaport Village
Seaport Village is a waterfront shopping and dining complex near both Downtown San Diego and the Embarcadero. With four miles of cobblestone pathways bordered by lakes, fountains, colorful landscaping, and even a quarter-mile boardwalk along the San Diego bay, it makes for a romantic place to take that special someone.
Headquarters at Seaport Village, formerly headquarters to the historic original San Diego Police Department, is one of San Diego’s most exciting new retail destination. Famous for its eclectic blend of classically inspired architectural styles and rich history, Headquarters makes for an exciting second date.
After sunset, dance the night away with Manny Cepeda and his orchestra with salsa, merengue, cumbia, bachata, and Cuban music in the beautiful outdoor courtyard. There is no experience necessary, but if you’ve got the epic dance skills, don’t hesitate to show them off to your date in this judgement-free dancing zone.
10) Visit a Winery
In San Diego Country, you can meet actual winemakers at intimate boutique wineries, most of which have been built by the winemakers themselves. You can stroll with your date, through mountainside Zinfandel vines, or take a horseback ride to a Spanish Albariño at a lovely hacienda property, enjoy beautiful live music, charming artwork and Ruby Cabernet, or sit on a dog-friendly patio with a Petite Sirah.
There is something for all guests in wine country, but even the urban wineries of downtown and coastal neighborhoods offer a charming and authentic experience of wine making and tasting for couples to enjoy.
11) Choose Your Own Adventure in Old Town
Old Town San Diego, California’s first settlement, is a great cultural destination and makes for a great date. The Old Town Trolley Tour is a fun experience throughout the year, but during the Holidays you can check out the sights, learn the history of the city, and experience the sparkle of Christmas lights along with the glow of city lights at night on their City Lights Night Tour.
For a more interactive dating experience, take the Tequila, Tacos, and Tombstones Tour with us, where one of our knowledgeable tour guides will take you on a journey through the historical eras of the early Spanish settlements while sprinkling in some authentic and delicious food tastings, traditional cocktail samplings, and fun. Let us know that you’re on a date, and we’ll even throw in a special gift for the two of you.
If you aren’t taking a trolley tour, or adventuring with us, you can still explore the famously haunted Whaley House museum, eat at any of the town’s many Restaurants, watch a show at Cygnet Theatre or Old Town Improv Co., or even bring a picnic to eat in the middle of Old Town Park. There is so much to do in the Birthplace of California.
12) Experience a Country Christmas in Julian
A celebration guaranteed to get you and your date in the Holiday spirit, the town of Julian’s old-fashioned Christmas traditions (that go back to the days of horse and carriage and homemade pie) will have you wondering if you’re even in Southern California anymore.
There are hayrides, sleigh rides, breakfasts with Santa, a lighting of the town’s living Christmas tree, and even public readings from the Bible about the birth of Jesus for religious folks.
The woodfire aroma, neighborly atmosphere, and nip in the air from the snow capped Cuyamaca Mountains surrounding town makes for a more authentic country experience than any other place in San Diego, and will have you and your date wanting to snuggle up close in this great place.