Think Outside The Chocolate Box: 12 Unique Valentine Dates in SA

Ah, Valentine’s Day. As mid-February approaches and the H-E-B aisles are suddenly awash with various shades of pink and red, it seems that San Antonio takes on a particularly romantic glow...and we aren’t the only ones who think so!

Recently topping this list as the “most romantic city in the country,” San Antonio offers its own take on romance: a captivating mix of old-world Spanish charm, Latin-American passion, and Texas chivalry.

With that sort of resume, you can bet that our local Valentine’s Day options are anything but conventional. In this list, we’ve compiled 12 of our favorite spontaneous, offbeat, (and sometimes downright sultry) date ideas to make this year memorable.

For the Thrill-Seekers: Valentine's Dinner & Ghost Tours

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If you’d like an excuse to cling to your date this Valentine’s day, let the Sisters Grimm whisk you away on a spine-tingling adventure in Downtown San Antonio! The Valentine’s Dinner & Ghost Tour starts with a three-course candlelit meal inside the haunted Menger Hotel, tastefully paired with delectable ghost stories. After dinner, you and your date will have the option to explore the most haunted sites in San Antonio either by foot or on the “Ghost Bus”!

For the Old-World Romantics: Hotel Havana

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For the old-school romantics among us, we recommend heading to Hotel Havana, a lush, Cuban-inspired gem in Downtown San Antonio! Whether you check in for short stay or just for dinner, you’re sure to be charmed. The Hotel’s colorful, nostalgic vibes exude a hip sort of luxury, complete with leafy cypress trees, sparkling chandeliers, Bastrop Pine floors, and Smeg fridges stocked with Shiner Bock.

This Valentine’s Day, Hotel Havana is offering a special three-course dining event in honor of ”Love and Shiner”! For $150 per couple (or $125 per couple for in-house guests), enjoy dishes like Charred Tomato Bisque and Butcher’s Cut Steak paired with your favorite Shiner brews! Call the Hotel Havana Front Desk at (210) 222-2008 or email to reserve! (Note: the regular Ocho menu will be available on the patio and in the Havana Bar on Valentine’s Day with no reservations required).

For the Fitness Junkies: A Fun Run

Trade in your heels for running shoes and celebrate Valentine’s Day with a fun run! Head to the Cupid 5K Chase (Feb 11th, Northwest San Antonio) or the Be M y Valentine 5k (Feb 12th, Downtow n San Antonio) for a Valentine-themed workout.

For the Jazz Enthusiasts: Live Music

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If you’re still swooning over La La Land’s hopelessly romantic jazz vibes, this date invites you to recreate the scene! Let San Antonio’s newest music venue “Jazz, TX” sweep you off your feet and set the mood. The brainchild of local bandleader Doc Watkins, this venue is subtle, sly, and upscale without a hint of pretension. On the evening of Valentine’s Day, Jazz, TX (Central San Antonio) invites you to an evening of classic love soundtracks by Doc Watkins and Johnny P. 

The price includes the full Prix Fixe Italian menu, which will feature calamari, truffle ricotta stuffed tortellini, braised beef cheek, horseradish gnocchi, tiramisu, and more!

For the Old School Nostalgics: A Speakeasy

Image Courtesy of The Last Word

Prohibition may be long gone, but its mark on San Antonio cocktail culture is still in full swing! This Valentine’s Day, duck into one of the Alamo City’s speakeasy-style bars and enjoy a specialty drink. Sly and romantic, these dimly-lit spots are the very definition of a “hidden gem”! Located throughout Downtown San Antonio and South town, we recommend Th e Brooklynite, Bar 1919, The Esquire, and The Last Word.

For the Retro Guys & Gals: Bowlero

Re-live some childhood nostalgia at Bowlero, a modern spin on a retro bowling alley in North Central San Antonio! You and your date might just feel like high school sweethearts at this upscale gaming, bowling, and dining experience. After you’re finished with a game of bowling, try the zero-gravity ropes course, relax in a lounge area, or play arcade games.

For the Wannabe Florist: San Antonio Botanical Gardens

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Take your date outside! Even in February, enjoy the gorgeous blooms at the Botanical Gardens, a Central San Antonio treasure offering 38 acres of flowers, paths, and trails. From the modern architecture of the Lucile Halsell Conservatory to the serene Japanese garden, you and your date will have plenty to admire. When you’re finished taking in all the scenery, you can stop in for a bite at Anne Marie’s Carriage House Bistro. Besides delicious food, this peaceful spot offers build-your-own mimosas!

For the Breakfast Lovers: Waffles For Dinner

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The whole “candlelit bistro” thing may be a classic Valentine’s Day setting, but we feel like breaking the rules this year. Try a breakfast-for-dinner approach to Valentine’s Day Guenther House Restaurant, famous for its oh-so-delicious breakfast menu served all day! We recommend the strawberry sweet cream waffles, followed by a romantic stroll in the historic Ki ng William neighborhood.

For the Burgeoning Chef: The Pearl Farmers Market

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Cooking at home for Valentine’s Day? Take your culinary art to the next level with fresh ingredients from the award-winning Pearl Farmers Mark et in Central San Antoni o! Open on Saturdays from 9:00 AM-1:00 PM, this colorful weekly event offers everything from chocolate to kale to farm-fresh eggs. You and your date can leisurely stroll the vendor lanes and find the perfect ingredients.

For the Poet: Pony Express Love Letters

For those who find pen-and-ink love letters to be the pinnacle of romantic expression, don’t miss The Briscoe Museum’s annual “Pony Express Love Letters” event! This movement seeks to spread a little old-fashioned love across the city by making space for starry-eyed writers to craft their own romantic piece of snail mail. Drop by the Museum in Downtown San Antonio anytime between February 4th-11th to write your letter, which will be delivered by bicycle later in the week.

For the Showstopper: An Acrobatics Performance

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For a truly thrilling show (in a truly magnificent setting), head to the Majestic Empire Theatre in Downtown San Antonio this weekend to see The Pecking Acrobats perform! As self-described “masters of balance,” this group of gymnasts will show off a wild array of trick-cycling, precision tumbling, somersaulting and gymnastics, defying gravity to a soundtrack of ambient live music. The show will take place on February 10th at 7:30 PM.

For the Adventurous: Mission Reach Trails

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Looking for an outdoorsy sort of Valentine’s Day? Take your date on an adventure and explore the extended River Walk trails! The Mission Reach trail includes over 15 miles of both urban and natural beauty stretching from Downtown San Antonio into South San Antonio. The trails feature the natural ecosystem and wildlife of the area, as well pedestrian bridges, pavilions, and access to views of four old Spanish missions (Concepción, San José, San Juan and Espada). San Antonio BCycle offers bicycles for rent throughout the downtown area, and vendors like Texas Pack and Paddle offer canoe and kayaking rentals. Explore the trails at sunset for an extra dose of old-world beauty.

While we’re busy swooning over our gorgeous city, we’d love to offer you an exclusive free download of our San Antonio Buyer’s Guide! When you’re ready to fall in love with your own little piece of San Antonio, we’ll set you up with the perfect home.