Your Next Trip: Five Things to Do in San Antonio, TX

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I’ve gotten a little backed up in travel posts. Okay, a lot backed up. I have trips from more than a year ago I need to queue up…cue grimacing/apologetic-looking emoji here. But with my mom and Oscar heading to San Antonio in the near future, I figured it couldn’t hurt to round up a few of my favorites from my quick weekend visit to San Antonio last year (!).

Prepared for the worst because it’s not Austin, I actually enjoyed San Antonio way more than I expected, despite slipping and falling TWICE on our hotel’s slippery walkways. Despite the humidity-induced wipeouts, I fully endorse San Antonio for a weekend getaway, especially if you go with markedly low expectations. You’ll be pleasantly surprised.




The Esquire Tavern
Before I interned at Esquire, before New York was even a blip on my radar, I had a deep and abiding love for Esquire. So of course I wanted to go to The Esquire Tavern based on name only, but it also ended up being one of the best stops on the trip. We went at least twice during our two days in town.

Located on the second floor of a building right on San Antonio’s river walk—which doesn’t have any rails to prevent drunks/small children from falling in, a fact that continues to blow my mind—The Esquire Tavern boasts the longest wooden bar top in Texas (more than 100 feet). The bar definitely has a speakeasy vibe, with baroque-inspired wallpaper, tufted leather booths, dim lighting, and the requisite bartenders in suspenders. And while the prices of the cocktails match the vibe, the house creations are fantastic. The smoky-sweet Capone’s revolver ($12)—Templeton rye, Kona coffee liqueur, and fire and damnation bitters—was a particular hit with our group, as were the tacos con papas and bloody Mary shrimp cocktail. I still think about those tacos con papas in their crunchy taco shells.

Go at night to see The Esquire Tavern in all its candle-lit glory, or stop during the day and nab a seat on the balcony, where you can watch the boats float by on the river walk. Also, definitely plan on breaking the seal there. The bathrooms look like some Return to Oz shit, wheelers not included.





El Mercado
We were in San Antonio during the winter, so we didn’t get to experience the outdoor market, but I loved browsing the indoor version. Rows upon rows of little storefronts hawk trinkets and souvenirs. Yes, it’s touristy and not particularly cheap, but it’s great for killing an afternoon and plotting your apartment’s future transformation into an ode to Dia de los Muertos. Bonus points if you stop into Mi Tierra Café & Bakery for a Mexican pastry. Opt for something with a filling of sorts to avoid the drier aspects of Mexican baked goods. I really wanted some of the restaurant’s mariachi band, but they were off on that day or something, or the restaurant was undergoing repairs. I don’t know how that scheduling works. You figure it out and get back to me with your tales of mariachi delight.


Tower of the Americas
Yes, another tourist stop. What, you’re a tourist, right? I describe Tower of the Americas as San Antonio’s Space Needle, which probably isn’t fair to the tower but pretty accurate. It dominates the skyline and acts as San Antonio’s main tourist draw, outside of the Bieber concert I’m pretty sure was going on the weekend of our visit. Like any other tower, you’re going to get to the top, check out the views, and be done, but hey! You did it! I highly suggest grabbing a drink at the Chart House Restaurant and watching the sunset as you sip your overpriced libation at the bar, but then again I think every tourist attraction could be improved with booze.


The Alamo
You’ve got to go in. Even if you don’t care about history (guilty), the whole story of loss and bloodshed and murder and abandonment will probably be close enough a serialized crime drama to keep your interest. If you, like me, know nothing of the monument’s past aside from “shit went awry,” I’d suggest at least springing for the audio tour. It’s only $7, and at 45 minutes long it will help ensure you spend a proper amount of time exploring the monument while your boyfriend reads every plaque. I also remember some spiffy sound effects, but I could just be making that up.



Dick’s Last Resort
I recommended this to my mom, and then immediately thought, “wait, I probably shouldn’t have sent my mom to a dive bar where they’re intentionally rude to you and then yell at you to get out while showering you in bar napkins.” But that’s pretty much Dick’s in a nutshell, and it’s an experience. I’ve never been to the Vegas iteration, but I assume it’s a pretty similar idea. Known for its surly bartenders, Dick’s seems to be a favorite with bachelor’s parties and groups of college kids, who bask in their mistreatment. Dom and I went after a few drinks, probably because I love kitsch, and got to experience the bar napkin shower. We also ran into a trashcan painted like R2D2, so bonus points there. Go at your own risk. I don’t remember what those paper hats were all about, but I’m sure they’re paramount to your humiliation.



Bonus: The River Walk
Less of a specific destination and more of an overarching feature of San Antonio’s main drag, The River Walk is actually pretty magical, if only that it demonstrates the city’s trust of its populace and its ability to not fall in. We were lucky enough to be in town during a music festival and got to watch a band play on a little island across the river, other roving bands bump some music from moving boats, and a Mexican Elvis get down with his bad self. I can’t endorse any of the restaurants located riverside, since most were forgettable, but just walking it and marveling at your own ability not to fall in is a good time. Think Amsterdam canal, but in Texas and teeming with overweight middle-Americans in clothes that most likely came from Wal-Mart. Okay, I’m really not selling it, but it’s a good time. I swear.


[Images: 1, 2, 12 by Dominic Moresi : 3–8, 13, 14 by Kristen Haney : 9 : 10 : 11 ]



  1. Cel Haney · · Reply

    Perfect timing! Very entertaining; can’t wait to act on some of your suggestions. I think.

    1. Just be careful on those walkways if it’s humid!

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