48 Hours in San Antonio

Good morning!  How was your weekend? I was in Chicago until Saturday evening, and on Sunday we got to celebrate my little nephew’s 3rd birthday. He’s so cute and I love watching his relationship with his cousins grow.

Last weekend we celebrated my friends’ 50th birthday in San Antonio.  It’s one of those things where we knew we wanted to do something extra special for the occasion and this trip was just the thing.  It turned out to be such a fun time, so I wanted to share all the details with you in case you wanted to plan something similar.  And don’t worry, I’ll be sure to share the Chicago trip recap with you soon too!


San Antonio is three hours from Houston and all five of us drove together in one car (a big van).  We got a suite at the Marriott River Center so that we could all stay together too.  Part of the fun is getting ready together and those late night conversations that only tend to happen after you’ve spent all day together.

48 hours in San Antonio - black jumpsuit with miller sandals

JumpsuitMiller SandalsWrap BraceletBag Sold Out (similar on sale)

For the ride up there, I wore this tank jumpsuit that’s quickly become a go-to for travel (wore it to NYC too) and all-around comfort. I love the relaxed fit, but still think it looks chic.  I’m wearing a size small.


The Marriott Rivercenter is right on the famous San Antonio Riverwalk that’s lined with tons of restaurants and shops.  You can do a boat tour down the riverwalk so that you can see all of it from the water.  Kids especially love doing that!

48 hours in San Antonio - girls trip

Jamie • Andrea • Ali-Shaun • Manuela

Stripe Top • Jean ShortsStudded SandalsSunglassesBag Sold Out (similar on sale)

The top is the same one you saw in my most recent Dressing Room post.  It was perfectly casual, but super soft and flattering with the shape. It fits TTS, I’m wearing size XS.

For dinner, we went to Mi Tierra, a four generation restaurant that began with just three tables 60 years ago, and is now a 24-hour 500 seat restaurant.  Known for their amazing Tex-Mex and uber delicious meat, Ali-Shaun and I shared fajitas.  Their margaritas are memorable too.

48 hours in San Antonio - Margarita


The next morning, we got up and got ready for our Cottonwood Wine Tour.  Cottonwood Wine Tours is a small family business owned by Matt (who ended up being our driver and guide) and his wife, Brandy.  Our entire tour involved brunch, shopping, then the wine tour.

48 hours in San Antonio - riverwalk

Matt picked us up at the hotel at 8 a.m., and drove us to Guenther House for a lovely breakfast.  Mr. Guenther was the founder of Pioneer Mills Flour. Fun fact : For the last three years, Guenther was developing the bun for McDonald’s McGriddle Breakfast Sandwich.

48 hours in San Antonio - backyard party

The weather was mild, so we got to sit outside and enjoy the meal.

48 hours in San Antonio - floral top and a black hat

Floral TankHat

48 hours in San Antonio - eating lunch outside

48 hours in San Antonio - restaurant

Their breakfast menu features items that allow their flour to shine, dishes like waffles and breakfast tacos, and of course, biscuits!  Their signature coffee is delicious too.

48 hours in San Antonio - waffles and coffee48 hours in San Antonio - breakfast burritos and hash browns48 hours in San Antonio - eggs and biscuits with gravy

Then we had time to peruse the on-site gift shop and peek into the museum that used to be Mr. Guenther’s home.

48 hours in San Antonio - antique room

48 hours in San Antonio - discount store


From there, Matt drove us an hour north to the Hill Country town of Fredericksburg, where we got to stroll and shop for about an hour and a half.  We could have stayed shopping longer and agreed to come back and actually stay in Fredericksburg at one of the quaint bed and breakfasts next time!

48 hours in San Antonio - stripe tank with amazon hat

Stripe TankHatSunglasses

Oh man, did Ali-Shaun regret not buying those sunglasses, they looked awesome on her!  She was researching where she could buy them online when she got home and found a similar pink pair at Nordstrom.

Fredericksburg has over 100 shops along Main Street, most of which are small boutiques as opposed to chain retailers.

Lock Stock & Barrel was one of my favorite stores, with unique kitchen and home decor items, along with nibbles to taste and buy.

Our last shop was the one we ate our way through!  It’s called The Tasting Place and you can sample almost every single thing they sell, all kinds of jams, mustards, sauces, relishes, tapenades, you name it.  I left with three bottles and could have bought more!


Then, it was onto 1851 Vineyards who makes Sister Creek wine for a tour of their winery and wine tasting.  I was worried about drinking so much wine, but it turns out that we sampled 8 wines (every variety they make) and the pour is so small that even if you drank every drop, it’s only 5 ounces.

Matt was knowledgeable about the wines and process, but I admit, most of what he said went over my head.  I know what wine I like to drink, but I don’t know much more than that!

We got to tour the production area, hear about how the wine is made, and see the many barrels.

The wine manager at Sister Creek was awesome too.  He’s an expert in the field, passionate about wine, friendly and fun- a perfect combination for a wine tasting!


We came back to the hotel with a couple hours downtime before getting ready for dinner. Ali-Shaun and I ran out to the Riverwalk to pick up souvenirs for the kids.  I found James a Davey Crockett hat, San Antonio keychain, stickers, and a book about the Alamo.  Jordan got a Frida Khalo coin purse and a lollipop.

Eyelet TopJean ShortsMiller SandalsSimilar SunglassesHat


For dinner, we had planned to all wear little black dresses, so that Andrea could shine in whatever she wanted to wear.  I was super happy in this flowy, pleated dress.  It’s forgiving and fully lined- great for a big dinner out on the town!  It’s racerback style in the back and also comes in a fun red snake or abstract zebra print. I’m wearing size XSP.

Pleated Black DressSnake Clutch

Ali-Shaun brought jeans and I didn’t let her live it down. At least they were black! 😉

48 hours in San Antonio - girls in all black

Dinner was at Plaza Club, a sister restaurant to the Houston Club where one of our friends, Manuela, is a member.  The restaurant is way up high so you got a beautiful view of the riverwalk and San Antonio skyline.  Sitting there at sunset with all of these beautiful ladies, we laughed, shared intimate stories, and ate the yummiest banana foster bread pudding.  It’s seriously up there with my all-time favorite desserts, and I’m usually a chocolate girl!


  • Have one person pay for all the meals, tips, coffees, etc. and then she can total everything up and divide equally among the group.  The others send their share to her via Venmo.
  • Have a general idea of what you’re going to do before you go.  Nothing worse than not being able to decide where to eat when everyone is starving.
  • Let the early risers make the coffee run for the rest of the group.
  • Be flexible.  Allow for some down time and if it’s a longer trip, some alone time for those that need it, or if you do.
  • Take photos.  Ask strangers to take group photos so you can all be in them.  You will cherish those pictures later. Windy hair and all!


I asked y’all in my weekend newsletter for restaurant recommendations and got a lot of great responses.  I wish we had more time to visit them all, but I’m bookmarking them for next time!

Mi Tierra – 24-hour Tex Mex and get the fajitas

Paesano’s –  several people recommended this restaurant that combines shopping with dining

Whiskey Cake – serves brunch, lunch and dinner with ‘social hour’ from 3-6 and 9-11 p.m.

Biga on the Banks – new American cuisine on the Riverwalk, earning rave reviews for innovative cuisine in fine dining

La Fogata – for delicious margaritas

La Hacienda De Los Barrios – If you love Mexican food, they serve delicious food (and margaritas!) and the atmosphere is really fun.


Six Flags Fiesta Texas – huge amusement park with lots of roller coasters.   This summer, a new ride, Joker Carnival of Chaos, was introduced as one of the world’s tallest pendulum rides.  Standing at a record-breaking 17-stories in the air, this impressive giant disk will reach speeds up to 75 miles per hour.  See my post about Six Flags and JW Marriott Resort here.
Natural Bridge Caverns – be prepared to carry young children, it’s a bit of a hike through the cavern
Kiddie Park – Established in 1925, and renovated in 2009, Kiddie Park is the oldest children’s amusement park in the country! While modern updates have been made, the park has preserved it’s 1920’s style by maintaining all of the original rides.
Pearl Brewery – located just north of downtown, the former brewery (operating from 1883-2001) is now home to The Culinary Institute of America, San Antonio, the year-round Pearl Farmers Market, Hotel Emma and its restaurant Supper.  You can spend hours browsing the shops, coffee houses, and ice cream shop.
48 Hours in San Antonio
I’m so glad we made this trip happen.  With everyone’s busy schedules and families, it’s hard to carve out the time, but it’s so worth it.
Have you been to San Antonio?  Let me know if there’s something I missed!  If you’re heading there soon, I hope you have a great time.  And if you book a Cottonwood Wine Tour, tell Matt that Megan sent ya. 😉
Have a great week friends!

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Meet Megan

Hi! I’m Megan, mom to a thoughtful teenager and spunky young girl. We call Houston home and recently moved into our dream home. I traded my lawyer hat to become a full-time blogger in 2010. I love sharing my passion for affordable fashion, home decor, organization, & fitness to help inspire you to take care of you!


  1. I live in San Antonio . . well, the outskirts of San Antonio . . . Helotes! It’s hard to do everything in a weekend, but fun to try!
    Here are a few other suggestions:
    Shopping at The Rim – close to La Cantera, anchor store is Bass Pro Shop.
    Floores Country Store, Helotes, Texas – Dance Hall (Home of Willie Nelson) Check the website for concerts.
    Boerne, Texas – like Fredricksburg, but a lot closer.
    Comfort, Texas – Smaller version of Boerne, just a few miles from Boerne.
    Luckenbach, Texas – Need I say more!
    New Braunfels, Texas – Tubing down the Guadalupe River, lunch at the Gristmill & drinks at Gruene Hall!
    Lots lots more to do . . .

    1. Hi Wanda! Thank you for so many more great ideas! It’s been forever since I’ve been to New Braunfels, but such a fun time!

  2. What a fun weekend! I’ve always wanted to go to San Antonio. I’m bookmarking this for sure! What’s the best time of year to visit?

    1. I’m from San Antonio and i would say not to go in the spring or summer. Fall and winter are your best bet for actually enjoying a good weather day.

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