20 Actually Cute Holiday Date Ideas in San Antonio 

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Whether you're in a long-term relationship or dating someone new (it is cuffing season, after all), here's some cute date ideas for you and your boo to enjoy this holiday season in San Antonio.
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Have a photoshoot in front of the official Christmas tree at Travis Park
Free, 301 E Travis St, (210) 207-3677, travisparksa.com
It’s Christmas season now that the city’s official Christmas tree has been lit. The official lighting of the tree takes place the day after Thanksgiving, so after that, holiday-themed dates are fair game. If only shopping centers could get the memo and not start playing Christmas music the day after Halloween.
Photo via Instagram / skylinedronetx
Test your knowledge of The Office during a Christmas-themed trivia pub crawl
$20, Downtown, Friday, Dec. 13, inkarn8.ticketspice.com
Tickets are on sale now so get them while you can! They cost $20, so that means it’s only $40 to take your boo on literally the best possible event you can think of as long as they’re a fan of The Office. Your ticket will come with a themed shirt, a Dunder Mifflin ID card, and entry into the trivia competition, so you can get your competitive spirit excited along with your holiday spirit. Themed drinks and food will be available.
Photo via Facebook / The Office
Get lost in Tim Burton’s world at Nightmare Before Christmas Bash on Friday the 13th
$5-$40, Friday, Dec. 13, VIBES Event Center, 1223 E Houston St, eventbrite.com
Do you get excited thinking about The Nightmare Before Christmas? Though there’s been a Nightmare Before Christmas bash every year for a decade now, this one is extra special because it falls on Friday the 13th. Get ready for an extra-spooky mashup where the iconic Tim Burton film meets Camp Crystal Lake. There will be a ton of vendors, live music, food trucks, costume contests and cash prizes. The family portion lasts from 6 p.m. to 9 p.m., and after that, the late-night fun begins.
Photo courtesy of Buena Vista Pictures
Share a kiss at midnight at the New Year’s Eve party at Hemisfair
434 S Alamo St, (210) 709-4750, hemisfair.org
Never forget to give someone a kiss at the stroke of Midnight on New Year’s Eve so you can start your year off right. It’s just like a million times better when that person is your one and only — no matter how long you’ve been dating — you’ve been waiting all night to kiss.
Photo via Instagram / therobfather917
Keep the Christmas celebrations going with Moscow Ballet's Great Russian Nutcracker at the Majestic Theatre
$33-$73, Thursday, Dec. 26 and Friday, Dec. 27, 224 E Houston St, (210) 226-5700, majesticempire.com
If you’ve never seen this classic iteration of the story of The Nutcracker, you’re missing out on a worldwide Christmas tradition. Even though the play is only performed for a short period of time and it doesn’t make for the cheapest date on this list, it’s worth it without a doubt to see the live show at the Majestic Theater. Plus, now you’ll know where all of those popular mystery Christmas music instrumentals come from.
Photo courtesy of the Moscow Ballet
Take in the seasonal classics at San Antonio Symphony’s Holiday Pops concert
$15-$100, 8pm, Saturday, Dec. 21 and Sunday, Dec. 22; 2pm, Monday, Dec. 23, Tobin Center for the Performing Arts, 100 Auditorium Cir, (210) 223-8624, sasymphony.org
Going to a San Antonio Symphony — or any symphony, really — is the perfect way to impress your crush. It just sounds so sophisticated to say that your first date (or third or hundreth) was going to the symphony. It’s extra special because you’ll be able to catch the Christmas classics while Holiday Pops is going on, which may put you in the mood for some cozy cuddles afterward.
Photo via Facebook / San Antonio Symphony
Celebrate Chanukah at the Historic Pearl
Free, 303 Pearl Pkwy, (210) 212-7260, facebook.com
Hosted by Young & Jewish San Antonio, Chanukah at Historic Pearl is free and open to the public. Even though the official celebration takes place on December 23, the menorah at Pearl will be lit each night of Chanukah in keeping with tradition. The celebration will have live music and kosher tacos, and is the perfect place to bring take your boo to celebrate.
Photo courtesy of Giant Noise
Sing along with carolers on the River Walk
Dec. 5-22, 6-8:15pm, Monday-Thursday; 6-9:30pm, Friday-Sunday, thesanantonioriverwalk.com
Nothing will get you in the holiday spirit quite like singing Christmas music. The best part is that other people are taking the lead if you’re singing along with carolers, so you’re not the only dorky one. If your date thinks this is lame, dump them. All you wanted for Christmas was them, but they didn’t even want to sing along with you.
Photo via Instagram / thesanantonioriverwalk
Indulge in tamales at La Gran Tamalada at Market Square
Free, Saturday, Dec. 14, 11am-7pm, Historic Market Square, 514 W Commerce St, .facebook.com
La Gran Tamalada honors the holiday-time tradition of making tamales. If you and bae are foodies, there will be a hands-on tamale making workshop from noon to 4 p.m. that will guide you through all the steps. There will also be lectures on the history of tamales that you can attend, if you’re into that. Even if you and your sweetheart aren’t much of the cooking type and don’t care to learn, there will also be tons of tamales available for purchase to take home and enjoy later.
Photo by Drew Patterson / Neptune9 Photography
Get lost in the Christmas light displays around town
Here are the best displays in the city.
Imagine being surrounded by thousands of dazzling and twinkling lights, a hot cocoa in one hand and your boo’s hand in the other. Christmas music is playing in the background and there may even be a chilly wind to tousle your hair. That date would be just like the coziest, corniest movie straight from Hallmark or Lifetime or whatever but it would be a ton better because it would be real and you’d be hanging out with your S.O. You can catch the best Christmas lights in Windcrest, Monte Vista and UIW to name a few if you want to stay local, but there’s lots of places worth the drive.
Photo via Instagram / christmaslightfest
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Be wowed by skilled acrobats at Cirque Musica: Holiday Wishes
$45-$85, Monday, Dec. 23, 7pm, Tobin Center for the Performing Arts 100 Auditorium Cir, (210) 223-8624, tobincenter.org
Cirque Musica blends wow-worthy circus acrobatics and holiday cheer with a symphony orchestra, so you’re basically getting two sensory overloads at once. The acts also tell a holiday-themed story (the details of which are top secret) and rumor has it that there is humor to the show as well as the stunning aerial stunts performed by the actors.
Photo via Facebook / Cirque Musica
Take part in the Posada at the Historic Pearl
Free, 303 Pearl Pkwy, (210) 212-7260, atpearl.com
In Mexican and Latin American culture, Las Posadas is a nine-day Christmas celebration that re-enactments Mary and Joseph’s quest to find lodging in Bethlehem. In Posada at the Historic Pearl, the evening celebration is compacted into one night. There will be live music, crafts for kids, and traditional treats of buñuelos, tamales and Mexican hot chocolate. Plus, it’s free!
Photo courtesy of Giant Noise
Laugh along to Elf the Musical at the Public Theater of San Antonio
800 W Ashby Pl, (210) 733-7258, thepublicsa.org
The original Elf? Hilarious. Elf the Musical? Your sides will hurt. Tickets range anywhere from $20 to $40. Your lover think this is lame? We only have one thing to say — there’s room for everyone on the nice list, except you.
Photo by Siggi Ragnar
Celebrate the culture at a Las Nuevas Tamaleras show
Now through Dec. 15, Friday-Sunday, 411 SW 24th St, (210) 434-6711, lastamaleras.com
Las Nuevas Tamaleras is as much tradition in San Antonio as The Nutcracker, but obviously in a more puro San Antonio way. The play follows the story of three ladies as they attempt — both hilariously and sincerely — to make tamales for the first time, joined by spirits who occasionally try to help. You can catch this show every Friday, Saturday and Sunday at OLLU. Tickets range from $15 to $25, depending how good you want your seats to be.
Photo courtesy of Burras Finas Productions
Catch a seasonal flick courtesy of Slab Cinema
Multiple locations, slabcinema.com
By seasonal flick, we mean Christmas movies! While some of the choices are a little funky (think Muppet Christmas Carol), others are pure gold (think Will Ferrell’s Elf) and others are just plain classics (think How the Grinch Stole Christmas). No matter which of the seven scheduled movies you see, you’re gonna have a good time snuggled up in your blanket with boo.
Photo courtesy of Walt Disney Home Video
Hit up an Ugly Christmas Sweater party
There’s no guarantee that these sweaters will be kid-friendly, so if your date has little Santa-believers, for the love of Christmas spirit, leave them at home. Ugly sweater parties can range from mildly sassy to outrageously offensive. Sometimes you’ll find Santa using a chimney as a toilet to something that’ll definitely get those folks on the naughty list, but there’s rarely an in-between.
Photo via Facebook / Bentley's Bar‎
Practice your best “choo-choo” at Santa’s Railroad Wonderland
11731 Wetmore Road, (210) 490-3554, txtransportationmuseum.org
The Texas Transportation Museum might not sound like the ultimate destination on a sweltering Wednesday in July, but when the weather is nice enough to enjoy the outdoors and everything is lit up for Christmas, it’s an adorable place to be. They light up the antique train engines and other vehicles on the property, and a train ride is included in admission. The holiday theme runs on Saturdays and Sundays from December 7 to December 22, and tickets are only $12 for adults. The ticket price includes free parking and a train ride, so bring your camera.
Photo via Facebook / Texas Transportation Museum
Support local artists (and get last minute gifts) at Brickmas
Free, Saturday, Dec. 21, 10am-6pm, 108 Blue Star #1773, (210) 262-8653, facebook.com/BrickmasHolidayMarket
Not *everyone* waits until the last minute to buy Christmas gifts...but highkey, most of us do. Put your dollars back into the community by supporting local artists and makers at Brickmas, where you can get cool, kitchy, handmade stuff that everyone will love. Everyone will be so distracted by how unique your gifts are that no one will know you bought them like a few days before Christmas.
Photo via Instagram / brickmas_sa
Get sentimental at the annual Star Wars Christmas Party at Brass Monkey
No cover, Saturday, Dec. 21, 9pm, 2702 N St Mary's St, (210) 480-4722, facebook.com
We find your lack of cheer disturbing. There’s absolutely no such thing as too nerdy. This year will be the 7th annual Star Wars Christmas party at Brass Monkey, which will kick off at 9 p.m. on December 21. Expect Star Wars decorations for days. Costumes are encouraged, so it’s the perfect photo op (and excuse) to dress up as Han Solo and Princess Leia with your crush.
Photo via Instagram / brassmonkeytx
Be amazed at the beautiful lights at Illume: Making Spirits Bright at San Pedro Creek Culture Park
Free, Saturday, Dec 14, 705 Camaron St, (210) 302-3652, sachamber.org
This year will be the second annual Illume at San Pedro Creek Culture Park. The one-night festival is meant to highlight the food, music, art and dance of the community. Not only will there be multicultural celebrations representing traditions from India, Greece and Korea, but there will also be a temporary art installation to illuminate the surroundings. Taking your cutie on a date like this is a lot like taking them to a museum, where part of the enjoyment of the evening comes from learning, but the bonding also comes from sharing new experiences together.
Photo via Instagram / sanpedrocreek
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Have a photoshoot in front of the official Christmas tree at Travis Park
Free, 301 E Travis St, (210) 207-3677, travisparksa.com
It’s Christmas season now that the city’s official Christmas tree has been lit. The official lighting of the tree takes place the day after Thanksgiving, so after that, holiday-themed dates are fair game. If only shopping centers could get the memo and not start playing Christmas music the day after Halloween.
Photo via Instagram / skylinedronetx

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