How to spend a weekend in San Antonio

Set in the heart of south-central Texas, where great, arid plains meet green rolling hills, San Antonio was founded as a Spanish colonial outpost in 1718, making it one of the oldest cities in the US. Now the second-largest in the state, it’s still defined by a blend of Mexican, Tejano (Texan of Mexican descent), German and Spanish influences and Texas’s distinct cowboy culture. All five of its historic missions are UNESCO listed and connected by a cycling and walking trail that weaves through colourful neighbourhoods and past peaceful riverbanks. The Alamo is the most famous as the site of the 1836 namesake battle, forever etched into the American psyche as a symbol of sacrifice, resilience and resistance. Also worth visiting are Mission San José, the largest and most complete, and Mission Concepción, which has remained largely unchanged since its dedication in 1755.

But the city’s more than just its past. San Antonio’s cultural pulse beats strongest in Downtown and along the famed River Walk, a 15-mile waterfront promenade following the San Antonio River. Initially planned as a controversial flood prevention system, it’s now the heart of the city and has served as inspiration for similar projects across the country, including Chicago’s Riverwalk. There are more than 600 pieces of public art — don’t miss the outdoor River Walk Public Art Garden with its 12 installations — and cultural hubs like the Witte Museum, spotlighting the state’s prehistoric past, and Briscoe, tracing the story of the American West.

What makes San Antonio a stand out, though, is its atmosphere. Despite its ever-expanding reach, the city’s maintained a unique small-town feel, anchored by a strong sense of community. Few downtown areas in America feel as welcoming and homely, thanks to equal measures of Southern hospitality and Latin flair. And while the annual Fiesta San Antonio — the city’s biggest cultural event with parades, food fairs and live music — is on for 10 days in April, the party here never really stops. Here’s how to spend a couple of culture- and history-filled days in San Antonio.

Day 1: Downtown discovery

Morning
San Antonio’s Historic Market Square has stood witness to the changing face of the city since it became a gathering place for Tejano communities in the 1800s. Vendors came together here during the day to sell fresh produce, and famous ‘chilli queens’ took over by night to feed the crowds steaming bowls of spicy beef stew. Today, it’s the largest Mexican market in the US, and you’ll find more than 100 locally owned businesses in its three-block outdoor plaza. Before exploring, get stuck into the handmade flour tortilla breakfast tacos at Mi Tierra — a family-owned restaurant for more than 80 years, it’s a true San Antonio landmark.  

Afternoon
San Antonio’s most recognisable area should be explored at water level, so descend to the San Antonio River for a Go Rio boat tour. The 35-minute loop around Downtown packs in urban stories, points out architectural marvels — such as the Fairmount Hotel building, which was moved in 1985 to avoid demolition — and spotlights public art. Then, visit The Alamo to learn about one of the US’s most famous battles, fought between Texan and Mexican forces in the state’s quest for independence. You’ll learn about local icons such as Davy Crockett, an American politician who lost his life defending the mission during a 13-day siege.

Evening
Plan for an early dinner at The Esquire Tavern. This is a speakeasy-style restaurant established in 1933 with dimly lit interiors and the longest wooden bar top in the state, making you half expect to see cowboys march through the doors at any minute. It’s known for its selection of local beers, so grab whatever appeals on tap and pair it with a pork belly torta and some fried pickles. Wrap up the day with the free Downtown at Twilight walking tour. A two-mile ramble across the district’s most significant sights, it uncovers San Antonio’s past through anecdotes and immersive storytelling. Afterwards, linger at the Main Plaza, where a nightly light show is projected onto the facade of the San Fernando Cathedral.

Day 2: Caves & culture

Morning
Arrive early at La Panadería to beat the queues that often snake around the block. Started by brothers José and David Cáceres to share their Mexican heritage and passion for baking, this cafe has built a cult following thanks to its unique 48-hour dough fermentation process. The Ranchero eggs benedict is a great choice for breakfast, and grab a selection of its baked goods, such as conchas (Mexican sweet bread) to go, too. Spend the rest of the morning at the Natural Bridge Caverns, around a 40-minute drive from Downtown. It’s the largest cave in Texas and has been designated a National Natural Landmark for its jaw-dropping stalagmite and stalactite formations, which resemble everything from a lunar valley to a giant’s throne. Most endearing are the so-called ‘fried egg’ stalagmites and discoloured draperies hanging from the ceilings and walls, features known as ‘cave bacon’.

Afternoon
To be called one of the best barbecue joints in Texas, especially in the face of seemingly endless competition and discerning diners, is no easy feat. If the hours-long peak-time queue and numerous awards are anything to go by, Pinkerton’s Barbecue is the real deal. This is no fuss or frills, just top-quality smoked brisket, ribs, sausages and sandwiches, served with classic sides executed to perfection. Walk the meal off with a visit to Hopscotch, a 20,000sq feet immersive art gallery. It features a permanent exhibition of 15 interactive installations that use light, sound and touch to play with the visitors’ perception of reality. Expect rooms resembling ice caves, a neon-lit mirror maze and even a trampoline.

Evening
The vision of one passionate local, the Pearl is a former brewery north of Downtown that’s been meticulously restored and updated to offer a complete neighbourhood experience, with independent boutiques, restaurants and bars, as well as a farmers’ and makers’ market on weekends. Explore the area, dropping into Pullman Market for some edible souvenirs, such as Texas barbecue sauces and seasonings, then sit for dinner at Southerleigh. Bringing together seasonal menus, coastal influences and 15 beers brewed on site, the restaurant has much to offer — not least the signature snapper throats. You’ll want to save space for the chocolate tart with tongue-tingling bourbon caramel and smoked marshmallow.

Where to stay

The heady mix of 1920s glam and Southern charm is hard to resist at The St Anthony Hotel. Luxury oozes out of every marbled column, crystal chandelier and fibre of the emerald-green rugs in the Peacock Alley, its city block-long lobby. The rooms are more understated, with a calming palette of grey, blue and white, and the outstanding service matches the demanding clientele, ranging from celebrities to cattle barons. It’s perfectly placed on the edge of Downtown, overlooking the green canopy of Travis Park.