How to Spend a Long Weekend in San Antonio

Buildings at Pearl Brewery in San Antonio lit at night

What do you get when you combine a three-day weekend, a chance to evade DC’s winter weather, and a sister who’s looking for her first getaway since becoming a mom of three? A long weekend escape to San Antonio! This historic city had been on my must-see list for quite some time. The Missions, the River Walk, the ability to eat tacos for every meal. How could one say no?

I took a different approach to planning this vacation. Outside of securing a place to stay, I didn’t pre-plan a thing. You heard that right, this super-planner planned nothing at all. The night before my flight I briefly skimmed a few articles, told myself we’d figure it out when we got there, and away we went.

DAY ONE: Everything’s Bigger in Texas…

We arrived in San Antonio late Friday morning and immediately checked into the Hilton Garden Inn Downtown, conveniently located one block from The Alamo and the River Walk. Our first order of business was to check out the downtown portion of the River Walk. At first glance, we were awe struck. Restaurant patios line both sides of the river while large trees provide a canopy from the streets above. However, it didn’t take us long to realize how touristy it is. It reminded me of Downtown Disney in Orlando; nice, but designed for tourist.

The Alamo in San Antonio lit up at night
The Alamo after-dark is a sight worth seeing, but to explore inside the mission and around the grounds, you'll need to go during normal business hours.

Our next stop was the Alamo. The Alamo is one of five missions in San Antonio. These missions were the colonization systems of the Spanish and date back to the 17th century. Four of the five missions combine to create the San Antonio Missions National Historical Park and, as of 2015, are recognized as a UNESCO World Heritage Site. The Alamo is the only mission that is not part of the National Park. The inside of the church is beautifully preserved and the grounds within the perimeter are well-kept and provide a lot of historical context. Be sure to check out the 150+ year old Live Oak tree on the premise.

The firepit at Down on Grayson and the tower at Pearl Brewery in San Antonio, TX
Down on Grayson fire pits (left); Pearl Brewery District (right)

That evening we headed to the Historic Pearl Brewery District. Pearl Brewery was the only brewery to survive prohibition. It eventually shuttered in 2001, but rather than demolish the complex, the building was re-purposed and the Pearl Brewery District formed around it. It has this old rustic, yet modern, vibe and most importantly lacks the touristy feel.

We had a rockstar Lyft driver (shout out to Allen, and to Lyft for the convenient timing of gifting me 50 percent off rides), who recommended we check out Down on Grayson for dinner. We snagged some chairs around a fire pit and sipped on local brews while we waited for a table in the dining area. We went the shareable plate route for dinner: casear salad w/pico de gallo, parmesan fries, the dip duo (jalapeno pimento cheese dip and quacamole), and the shishito peppers. I’d never had shishito peppers, so you can imagine my surprise when a plate of twenty-five peppers landed on our table. Is this normal or should I file this under “everything’s bigger in Texas”?  

The evening light show on the side of the San Fernando Cathedral in San Antonio, TX
Learn about San Antonio's history via light show at the San Fernando Cathedral

Later, we took another stroll along the River Walk to check out the night time vibe. Loud music caught our attention so we made our way to the street level expecting to find a band. Instead we discovered a laser light show on the side of the San Fernando Cathedral. The free, 24-minute light show depicts the history of the city. It was not what we were expecting to stumble upon, but 100% uniquely San Antonio!

The San Jose Mission and the bike trail that runs between the Missions in San Antonio, TX
Mission San Jose (left); Bike riding along the Missions Hike and Bike Trail (right)

DAY TWO: Those Sneaky San Antonio River Hills 

We kicked off Saturday with coffee and breakfast tacos at Revolucion Coffee + Juice, a plant-based coffee and juice shop that got its start in San Antonio. After our coffee and taco fix, we set out to explore the San Antonio Missions National Historical Park via bikes. The Mission Hike and Bike Trail, along the San Antonio River, provides access to the missions and was the perfect way to get to each one. The trail is paved, well-maintained, and well-marked. It’s extremely easy to find your way from the trail to the missions and back to the trail. At the entrance to the missions are SWell Cycle bike share kiosks, where you can rent a bike for $12/day. We started at Mission San Juan, the second farthest mission from Downtown, and worked our way back towards the city along the trail. Mission San Jose is the next mission you’ll come across. This place is beautiful. It feels like you you’ve been transported back in time. If you only venture out to one mission, this should be it! The last mission before you reach downtown is Mission Concepcion. Unfortunately, we weren’t able to explore this one due to the government furlough.

PRO TIP: The Hike and Bike Trail is not a flat ride. In fact, I was caught totally off-guard at just how hilly it was. On a day when the temps were around 60, we took several breaks to catch our breath, rest our legs, and grab some water. If you’re doing this on a warm day, be sure to bring plenty of fluids, dress appropriately, and wear sunscreen. There isn’t much shade along the trail!

Beer samples on the patio at Blue Star Brewing in San Antonio, TX
Grab a flight on the patio at Blue Star Brewing Company

Just when you think your legs can’t handle anymore peddling, there’s a saving grace. The Blue Star Brewing Company sits right along the trail on the way back to the city. This is a perfect spot to rest and refuel. We sampled the local beer and munched on nachos and brisket jalapeno poppers. I’m not usually a big fan of fried foods but the deep-fried brisket+cheese+jalapeno combo was worth every bite. We decided to ditch the bikes and walk the last mile. The route takes you through the King William historic district, which is lined with beautiful homes that have the same type of charm you find in Charleston, South Carolina.

That evening we dined at Feast, an American tapas place in the King William district with a daily rotating menu. They were busy so we had to sit on the patio with a heater, and though I would have preferred a little extra warmth, the food was worth it. We shared sourdough bread, pasta with kale, parmesan, and red chili peppers, and the spicy cauliflower. Feast has a nice large patio and on warmer nights, I can imagine it’s the place to be. But on this cool evening, we skipped the “sit and enjoy the space” part and booked it to Rosario’s, the nearest Mexican joint, to warm up with a margarita.

The wooden bar with drinks on it at The Esquire Tavern in San Antonio, TX
Sip cocktails on Texas' longest bar at The Esquire Tavern

We wrapped up the evening with cocktails at The Esquire Tavern. A former San Antonian suggested this place and who am I to pass up a recommendation from a local? The Esquire Tavern was everything I love wrapped into one establishment: bursting with history and delicious drinks. It opened immediately after prohibition ended in 1933. Its 100ft bar is the longest bar in Texas and when you touch it, you can tell the smoothness is from over 85 years of wear and tear. We sipped on the Commerce Street Fix and Nuestra Margarita. If you prefer your margarita less sweet, this is the spot for you. It was hands down our favorite!

A plant stand and a glass of wine at the Pearl Brewery Farmers Market in San Antonio, TX
The Pearl Brewery Farmer's Market is the ideal Sunday spot

DAY THREE: There’s No Such Thing as too Much Mexican Food

Shotgun House Coffee Roasters was our supplier of caffeine and breakfast tacos Sunday morning. This recently opened coffee joint is set up in an old warehouse and its walls are full of art by local artists. With absolutely nothing planned for the day, we decided to head back to Pearl Brewery to check out the shops. It turned out to be the best decision of the weekend. Not only were all the shops open, but there was a large farmer’s market in progress and the place was full of San Antonians (and their four-legged friends).  Every stand at the farmer’s market is required to get all of their products from with 300 miles of the city. We sampled local cheeses and vinegars, checked out local flowers and produce, and even purchased locally made lip balm (I regret not buying two). We sipped on Bending Branch wine and took in the sunshine, live music, and quite possibly every breed of dog in existence. We couldn’t pass up the chance for authentic Mexican food and indulged in brisket empanadas, chicken and beef tacos, and pork tamales. The Pearl Brewery Farmer’s Market is a must do while in San Antonio.

Nighttime at Market Square in San Antonio, TX
Market Square

Earlier in the weekend an Uber driver told us his favorite place for Mexican food was Pico de Gallo and another suggested we grab margaritas at Mi Tierra. Both places are located at the Historic Market Square, so we decided to do both. After chicken mole and chicken enchiladas at Pico de Gallo, we headed to Mi Tierra for drinks. The skinny margarita was one of the better ones we had over the weekend and the tequila flight ($12 for three samples) was a unique way to taste the difference between a Blanco, Reposado, and Añejo tequila.

A view of the Japanese Tea Garden in San Antonio, TX
Japanese Tea Garden

DAY FOUR: Ending the Weekend with a Little Zen

Monday morning we swung back by Revolucion for breakfast. The barista recommended we check out the Japanese Tea Garden, and since we had some time to kill before leaving, off we went. What we found was the most perfect zen space full of koi ponds, small stone bridges, and a waterfall. It’s about 10 minutes from downtown and though you only need to set aside about 30 minutes here, it’s the perfect escape from the busy city life.

San Antonio stole my heart. Whether you’re looking for the downtown tourist vibe or the laid-back local feel of Pearl Brewery, this city offers something for everyone. The history. The culture. The food. The people. It’s a destination that shouldn’t be skipped.

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Megan Beckley

Megan Beckley

I’m a wandering Virginia girl with a serious thirst for travel. When I’m on the road, I’ve got one goal: create an authentic experience without breaking the bank. When I’m not traveling, I maintain my 9-5 work-life while carving out time to play tourist in my own city.

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