Looking for a perfect blend of luxury, history, and charm? Hotel Emma in San Antonio’s Pearl District is the ideal escape, and just maybe, you might be willing to venture out farther. This stunning hotel is more than just a place to stay—it’s a complete experience, from its historic architecture to its thoughtful amenities like artisanal snacks and even a branded Laguiole corkscrew in the minibar. It’s such a fabulous experience that it just earned two Michelin keys!

Day 1 – Check into Hotel Emma & Explore the Pearl

Check into Hotel Emma, where your getaway starts with a welcome margarita at check-in. Stay in the charming Brewmaster building or the sleek River Cellar, both offering luxury with unique touches like nightly turndown service with macarons and artesian water.

Once settled, explore the Pearl District before heading to dinner at Best Quality Daughter. This former pop-up star now has it’s own brick and mortar location becuase it’s that good—be sure to try the boozy boba drinks (which pack a punch).

End the evening with cocktails at Stirnewirth, where craft cocktails meet a cozy, upscale atmosphere. If staying at the Hotel Emma, the Silo tables can be reserved in advance through the hotel’s concierge.

Day 2 – Breakfast, History, & Southtown Charm

Start your morning at Cullum’s Attaboy, known for its incredible SpudNuts, a potato-based donut (yes, I know, yet another donut recommendation). This neighborhood gem is perfect for a relaxed breakfast while listening to River Walk jazz.

Afterward, visit San Antonio’s most iconic site: The Alamo. Explore the grounds and learn about Texas history and this historic mission. After your self-guided tour, head over to the River Walk for a stroll along the canals (don’t worry, it’s always cooler down on the River Walk).

Lunch (or any meal) is a must at La Fonda on Main, where you can enjoy great food and killer margaritas. This San Antonio institution has been serving locals and visitors alike since 1932 and is a great place to catch up with friends.

For dinner, head to Bar Loretta in Southtown, where reservations are definitely required. This modern Texas bistro offers upscale comfort food in a lively atmosphere. To wrap up the night, check out Bar 1919, a hidden speakeasy known for its craft cocktails and extensive bourbon selection—finding the entrance is half the fun?!

Day 3 – The Alamo, River Walk, & More

Order breakfast to the room (which comes from Supper) to enjoy on your balcony.

Afterward, take your time exploring another section of the River Walk near Hotel Emma. Make sure to stop for a beer at Elsewhere Garden Bar & Kitchen, an Instagrammable garden oasis right off the River Walk. There’s also a great dog park/beer garden-type spot right next door if your canine friend is with you.

For a casual lunch, stop by Southerleigh Fine Food & Brewery in the Pearl for great food and a taste of their house-brewed beer—some of which are replicas of Pearl receips from decades past.

Spend the afternoon/evening wandering around the Pearl District, grabbing bites from the Food Hall at Bottling Department and Pullman Market. Consider stopping at Cured for their happy hour, which is known for $0.50 fried quail legs and half-price wines by the glass. Then, walk a few feet farther to enjoy the serene ambiance of the outdoor seating at High Street Wine Co. (if the weather is cool enough).

Day 4 – Brunch & Shopping

Kick off your day with brunch at NOLA Brunch & Beignets. The New Orleans-inspired menu features both sweet and savory beignets, and is a top brunch spot in the city.

Spend the afternoon shopping and exploring the Pearl District or head out to grab some filled churros from Honcho’s Churros (try the sweetened condensed milk filling).

For dinner, book a table at Brasserie Mon Chou Chou. This French brasserie in the Pearl serves up hearty dishes in a bustling atmosphere. Their bread, brought in daily from Houston’s Magnol French Bakery, is worth the visit alone so make sure to order a side of it.

Day 5 – Grab & Go

Before heading out of San Antonio, choose between two local favorites: 2M Smokehouse for some of the best BBQ in town (go early, they sell out fast) or Richter’s Bakhaus for cinnamon rolls as big as your face and straight out of the oven. Either way, you’ll leave the city with a satisfied palate and great memories.

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