The Ultimate 72-Hour San Antonio Getaway
San Antonio: Beyond the River Walk
Hello Internet! This year marks our 10th annual Mother-Daughter trip—a non-negotiable tradition (despite a brief Covid-related hiatus)! We’ve covered a lot of ground over the years—from the beaches of Curacao and Aruba to the history (okay, wine) of France and Italy. This year, we’re headed to San Antonio, Texas, to explore the local history and nearby countryside (okay, wineries) with a very special mission: to field-test and launch my brand new TCT Audio Guides!
After a decade of mother-daughter adventures, San Antonio surprised us with its warmth, depth, and history around every corner. The resulting itinerary is packed with high-value historical stops, delicious Hill Country escapes, and, thanks to the new guides, lots of education and inspiration.
Introducing the Tabby Cat Travels Audio Guides Project
For years, I’ve perfected the art of the self-guided tour—the deep dive without the expense or inflexibility of a group. This trip marks the official launch of the TCT Audio Guides, which allow you to recreate my meticulously planned adventures seamlessly.
We used two guides on this trip:
- The Palimpsest City Walking Tour — Covers the historic downtown core.
- The Mission Path Tour — A step-by-step guide for navigating (we chose e-bikes!) the Mission Trail.
Here’s how we used them to maximize our 72-hour adventure!
Day 1 – Arrival & River Walk Magic (Friday)
History, reflection, and dinner by the water: the River Walk experience that started it all.
We arrived Friday afternoon, checked in, and immediately headed for the most iconic spot in the city: the River Walk (Paseo del Río).
The River Walk’s beauty hides a dark beginning. A catastrophic flood in 1921 killed 50 people and nearly led to the river’s burial beneath concrete. Instead, a visionary plan saved it: a flood-control dam upstream, a bypass channel to manage flow, and a redesigned downtown loop that lowered the water level and created accessible banks. The result transformed a potential disaster zone into one of America’s most beloved urban parks—an intricate network of cobblestone paths, bridges, and hidden courtyards.
What many visitors don’t realize is that much of the River Walk we enjoy today was built and beautified during the New Deal era. Through the Works Progress Administration (WPA), thousands of local workers were employed to carve stone pathways, construct bridges, plant landscaping, and shape the winding walkways that define the River Walk’s charm. This massive public-works investment not only revived the local economy during the Great Depression but also helped solidify San Antonio’s identity as a city where history, labor, and imagination meet along the water’s edge.
Day 2 – Hill Country Escape (Saturday)
Saturday was all about getting out of the city and into the stunning Texas Hill Country, just a short drive away.
Morning Adventure: Beneath the Earth
We started the day exploring Natural Bridge Caverns, a vast underground world of towering limestone formations, dripping stalactites, and echoing chambers. It’s a jaw-dropping contrast to the man-made history of downtown.
Travelers often debate between Natural Bridge Caverns (about 35 minutes from downtown) and Cascade Caverns (near Boerne, roughly 45 minutes). Natural Bridge wins for scale and multiple tour options—but both offer an incredible glimpse beneath the Hill Country’s limestone crust.
Afternoon Adventure: Texas Wine Trail
After the caves, we followed the Texas Wine Trail, where rolling limestone hills and wide plateaus shape the flavor of every pour. The region’s high elevation, rocky soils, and long, sunny growing season create ideal conditions for Mediterranean-style grapes like Tempranillo, Viognier, and Sangiovese.
Mom and I, of course, have very different tastes—she’s firmly in the sweet camp (think Moscato and Late Harvest Rieslings), while I prefer something a touch drier but still approachable. Finding wineries that pleased us both took dedicated pre-trip research—but that’s where I come in! Strategic planning means you don’t waste a day driving to tastings that miss the mark.
Our curated route included three standout stops:
- Sandy Road Vineyards — A perfect lunch spot with outdoor seating and vibrant local wines.
- Airis’Ele Vineyards — Unique varietals, artistic flair, and sweeping views.
- Sister Creek Vineyards — Classic Hill Country charm inside a historic cotton gin.
The perfect mix of discovery, relaxation, and laughter—a quintessential mother-daughter day.
Day 3 – History & Lights
By Sunday, we were ready to get our steps in! With the TCT Palimpsest City Walking Tour Audio Guide queued up, we set out to peel back San Antonio’s many historical layers and burn off some of those wine calories.
Morning: The Heart of Old San Antonio
We started at San Fernando Cathedral, the oldest continuously operating religious site in Texas. Founded in 1731 by Canary Island settlers, the cathedral remains as much a community anchor today as it was nearly three centuries ago. The audio guide pointed out subtle details—like the blend of Spanish Colonial stonework and later French-Gothic touches—that you might otherwise miss.
From there, we walked to the Spanish Governor’s Palace, a graceful adobe structure that once served as the seat of government for the Spanish province. Its quiet courtyard and fountain offered a tranquil pause amid the city bustle—a glimpse of 18th-century life preserved in the middle of downtown.
A few blocks away, Historic Market Square (El Mercado) brought us right back into the color and energy of modern San Antonio. With handcrafted goods, murals, and the scent of delicious food in the air, it’s impossible not to linger. In fact, plan to linger longer than you expect! We spent a couple of hours browsing and shopping.
Before heading toward the King William District, we stopped at La Villita Historic Arts Village, San Antonio’s first neighborhood. Once a simple settlement for soldiers, it became a permanent village after a catastrophic flood in 1819 (see a pattern here?). It later played a small role in the Texas Revolution, declined into a slum in the early 1900s then was revived in the 1940s. Today, it’s a charming arts district filled with local boutiques and galleries.
Afternoon: From Power to Preservation
In the afternoon, we made our way to the King William Historic District, a peaceful stretch of tree-lined streets and stately Victorian homes once owned by German-American merchants and industrialists. The area is filled with ornate facades, cast-iron details, and deep wraparound porches.
We paused outside the Steves Homestead, a limestone mansion built in 1876 by Edward Steves, a prominent local lumber magnate. The home is no longer open for tours, but interpretive signs nearby share the family’s fascinating history. Even from the sidewalk, its grandeur speaks for itself—an echo of the city’s Gilded Age prosperity.
Evening: Dinner with a View & A Light-Show Finale
That evening, we treated ourselves to dinner with a view at the Tower of the Americas, a 750-foot icon built for the 1968 World’s Fair. Watching the city shift from daylight to dusk while the restaurant slowly revolved was pure magic—golden light on the Hill Country, the river glinting below, the Alamo glowing softly in the distance.
But the true highlight of the night came after dark: The Saga, a free video art installation projected onto the façade of San Fernando Cathedral. For 24 minutes, the cathedral becomes a living canvas—history, culture, and light blending into one unforgettable experience.
Day 4 – Bike & Beauty (Monday)
For our final day, we swapped walking shoes for e-bikes and followed the TCT Mission Path Audio Guide south along the San Antonio River Walk.
The Mission Path Ride
Our route followed the San Antonio Missions National Historical Park, home to four of the city’s five Spanish colonial missions: Concepción, San José, San Juan, and Espada.
We began at The Alamo (Mission San Antonio de Valero) downtown, then headed south. From the city’s most famous mission to its lesser-known gems, the trail traces centuries of cultural exchange and faith.
TCT Tip: Entry to the Alamo grounds is free, but reserve a timed entry ticket online if you want to step inside the church. It’s quick, easy, and saves you a long wait.
Each mission along the trail has its own personality:
- Mission Concepción — Nearly untouched since the 1700s, with original frescoes still visible on its interior walls.
- Mission San José — The “Queen of the Missions,” known for the stunning Rose Window and its beautifully restored church.
- Mission San Juan — Peaceful and pastoral, surrounded by fields that once sustained the mission community.
- Mission Espada — The oldest, and home to the original working acequia, an 18th-century irrigation canal still flowing today.
Riding between the missions gave us time to absorb not just the history, but the rhythm of the river itself. The TCT Audio Guide synced with our pace, blending storytelling with gentle navigation.
After finishing the trail, we headed back into the city and wrapped up our final night with tableside guacamole and margaritas—a perfect toast to four unforgettable days. Still not quite ready to call it a night, we wandered over to The Esquire Tavern, a legendary San Antonio institution. Opened in 1933 on the very day Prohibition was repealed, The Esquire boasts the longest wooden bar in Texas and quickly became a gathering place for everyone from workers celebrating the end of the dry era to soldiers passing through during World War II. Today, its speakeasy glow and historic charm make it the perfect spot for a final nightcap.
It was another unforgettable mother-daughter adventure, and I’m already excited to start planning the next one.