The best way to spend a long weekend in San Antonio

When my husband and I were trying to figure out where we wanted to spend our first anniversary, we both kept coming back to San Antonio as an option. We love to eat good food, drink local beers, and have a local experience when we travel, and San Antonio seemed like the perfect place!

San Antonio

Pearl District
We got to experience the Pearl District on our first evening, when my husband *willingly and excitedly* took anniversary photos with me. The Pearl District is a recently rehabbed brewery, developed into a park, shopping and restaurant district that’s really unique. They have a farmers’ market on Saturday mornings, and there’s plenty of restaurant options whether you want an upscale food hall-style meal, southern BBQ, or even a nice, sit-down meal. We really enjoyed Down on Grayson and the Granary. The Hotel Emma has an incredible lobby and a really great aesthetic, a great spot to grab a drink or a meal as well.


Ice Houses, Growlers Stations & Bottle Shops
The idea of a bottle shop is not huge in Illinois, so we loved stopping into places that sold bottled beer and felt like you were hanging out at a friend’s house. Another thing unique to the San Antonio & Texas area are ice houses, which are more or less no-frills bars with a ton of outdoor seating. We hung out at The Friendly Spot Ice House on our way to and from dinner in the Southtown neighborhood. Another great spot was The Luxury, just near the San Antonio Art Museum, overlooking the river.

Local Cuisine
I don’t think that we had a bad meal the entire time we were in San Antonio. My favorite dinner was had at a bright pink, former convent turned into a charming, locally sourced restaurant called the Liberty Bar. Our waiter was so friendly and knowledgable, and the from-scratch nature of the dishes was evident in every bite. The Downstairs at the Esquire Tavern is a phenomenal spot, staffed with amazing people who are extremely knowledgable about everything in their beverage program. The aesthetic there is kind of art deco with a mix of some taxidermy, and despite that sounding odd, it has a really cool vibe! Another place not to be missed is the Hoppy Monk, which has an insane brunch, and is worth the $30 Uber right just north of town.

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We quickly became obsessed with paletas from Steel City Pops– and by obsessed I mean one day we went twice, and we ate there every single day of our trip. Paletas are colorful popsicles, traditional in Latin American cultures. Steel City lets you choose your paleta, choose a chocolate to dip it into, choose your drizzle and a dusting of your choice. The great news is that this company is quickly making its way through the South, and even as far north as Louisville, KY. My husband assured me we wouldn’t be driving to Louisville just for paletas anytime soon, but you should definitely try some when you’re in San Antonio.

And of course- The Riverwalk
We had a lot of fun wandering around on the Riverwalk outside of the super busy downtown areas. The Riverwalk actually runs for about 30 miles through the downtown and surrounding neighborhoods, and feels extremely safe no matter what time of the day it is. Know that of course, the downtown areas are super touristy and not really representative of the city itself, but others areas off the beaten path are a great way to have an authentic experience. We wandered away from downtown to Blue Star Brewing and really enjoyed the area, as well as getting to the Alamo up close and person (spoiler alert- it’s a little smaller than you’ve been imagining it!).

We stayed at the Westin Riverwalk hotel, which put us steps from a bunch of vibrant neighborhoods in the area. We enjoyed relaxing on the rooftop patio & pool, and being right in the heart of the city.

Anything that I missed? Think that we need to take another trip back to check something in particular out? Leave a comment below and let me know what you think!


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