My sister, Janice, made the mistake of traveling with me.
She thought we were going to San Antonio for a relaxing birthday getaway. Three days of sightseeing, good food, and quality time together.
Apparently, nobody warned her.
I’ve always maintained that crazy things happen to me on vacation. This time, I had a witness.
And as it turned out, a very willing accomplice.
San Antonio, Texas, had been on my growing bucket list for years. I’d never visited, and there was something especially wonderful about finally exploring a new destination with someone I love.
Nothing particularly outrageous was on the itinerary.
Apparently, San Antonio didn’t get that memo.
The Grand Hyatt Riverwalk
We stayed at the beautiful Grand Hyatt San Antonio River Walk, perfectly situated for exploring the city on foot.
Sis arrived first, and with her name on the reservation, she was able to check in early. She scored a lovely room on the 23rd floor of the 24-story hotel and promptly took a nap.
Meanwhile, my arrival was considerably less efficient.
Being chronically directionally challenged, I somehow managed to explore the convention center, the second floor, followed by the fifth floor, while searching for Room 2304.
Yes, 2304. As in, the twenty-third floor.
Apparently, that minor detail had escaped me.
By the time I emerged from yet another elevator, my sister had launched a rescue mission.
She took one look at my thoroughly frustrated expression and started laughing into her sleeve.
There I was, walking in circles again.
We’d been reunited for approximately five minutes, and I was already providing the entertainment.
Welcome to San Antonio!
The Hotel’s Birthday Welcome
Later that evening, after we had walked 6.87 miles, I was relaxing in bed when I noticed two champagne flutes sitting directly in front of the TV screen.
“What’s that? That’s an odd place for two champagne glasses.”
Naturally, I had to investigate.
That’s when I discovered a birthday card, two lovely little boxes of chocolates, and a bottle of champagne conveniently chilling in the mini fridge.
“Look! Birthday gifts!”
I’d mentioned to hotel staff that we were both celebrating birthdays, but I certainly hadn’t expected such a thoughtful surprise.
Naturally, I immediately ate all four chocolates in my little box.
My sister demonstrated considerably more restraint.
Apparently, one of us has willpower when there’s chocolate in the room.
The champagne remained unopened throughout our stay, and we left it chilling in the refrigerator when we checked out.
Somewhere in San Antonio, a housekeeper may have enjoyed a rather festive weekend.
Two Sisters Walk into a Restaurant…
Our first evening, we wandered along the River Walk looking for dinner.
I wasn’t particularly hungry and suggested something light. Maybe a salad.
We stopped to read menus and eventually wandered into a restaurant called Dick’s Last Resort.
Now, I’d never been to Dick’s Last Resort. Neither had my sister.
And we had absolutely no idea what we’d just walked into.
As we made our way to our table, I noticed diners wearing tall, white, paper cone hats covered with handwritten messages.
How peculiar.
Then I happened to read one.
“I’m so old my STDs expired.”
The gentleman wearing it was laughing hysterically.
I was appalled.
What kind of restaurant was this?
Our waitress arrived and promptly tossed the menus onto the table. Silverware and napkins followed with about the same degree of finesse.
Well, this was certainly different.
As we studied the menu, I noticed an item called Dick’s Huge Wiener.
Ah. Things were beginning to make sense.
Apparently, we’d wandered into a restaurant where the staff was deliberately rude, the menu was questionable, and absolutely nothing was off-limits.
Meanwhile, our waitress was busy making those ridiculous paper hats.
“I won’t be wearing a hat,” I announced.
Famous last words.
As I looked around the restaurant, Sis pointed to another gentleman sporting a hat with a particularly outrageous declaration about being two inches from becoming a lesbian.
By this time, curiosity was getting the better of me.
What would the waitress write on MY hat?
I leaned into the adventure and decided to find out.
A few minutes later, I was proudly wearing a tall white paper cone announcing:
“Doggy style throws my hips out.”
Mine was accompanied by a friendly ‘gesture’.
Janice nearly fell out of her chair laughing and immediately started taking pictures.
Then the waitress plopped a hat onto HER head.
“They named the Great Depression after my ho-ha.”
Oh. My. Goodness.
Now we were BOTH laughing.
A grandmother and her two over-21 granddaughters at the table behind us were thoroughly entertained by our antics and decided they wanted hats, too.
Apparently, ridiculousness is contagious.
I sent photographs to my brother, Bob, in New Jersey.
His response?
“My kind of place … no filter.”
Despite the questionable hospitality, flying silverware, and completely inappropriate headwear, the Street Salad with grilled chicken was remarkably delicious.
Apparently, Dick’s Last Resort takes its cooking considerably more seriously than its customers.
Two Horsewomen and a Very Suspicious Sales Manager
The next adventure wasn’t exactly on our itinerary, either.
While wandering along the River Walk, we were approached by a friendly young man representing a vacation club.
Now, I normally avoid timeshare salespeople like the plague.
But Sergio was personable, and his offer was surprisingly tempting.
For attending a 90-minute timeshare presentation, we’d each receive a $125 American Express gift card, a complimentary River Walk boat tour— something we were already planning to purchase for $22 each, and a 3-day, 2-night stay at one of the club’s properties.
We looked at each other.
At virtually the same moment, we both said:
“I’ll buy your birthday dinner!”
There was just one small complication.
Apparently, to qualify individually for the promotional offers, we had to be single travelers and couldn’t present ourselves as traveling together.
My sister, who is married, cheerfully announced:
“Oh, I can be single if I need to be.”
And that’s when our undercover operation began.
Sergio arranged separate transportation. Sis departed from Margaritaville while he escorted me to the Hard Rock Cafe for another shuttle pickup.
An excellent plan in concept.
Except somehow, despite our elaborate transportation arrangements, I ended up standing in line directly behind my sister. Oops.
Inside, we sat at separate tables, carefully maintaining our status as two complete strangers.
The presentations continued well beyond the advertised 90 minutes, with managers circulating among the tables, attempting to close sales.
Eventually, one of the managers approached me.
“Are you here with anyone?”
“No, I’m a solo traveler. Why?”
She looked suspicious.
“Well, there’s another woman here with a very similar story. Horses … staying at the same hotel…”
“Really? Oh, wow! I’d love to meet her. We have things in common!”
She wasn’t amused.
“And you checked in one minute apart.”
I looked her straight in the face.
“What a coincidence!”
Apparently, my acting career had begun.
The manager looked increasingly unconvinced, but we maintained our composure.
We didn’t want Sergio getting into trouble.
We finally escaped, gift cards in hand, and boarded the return shuttle with several other women who had attended for much the same reason.
Naturally, everyone started comparing notes.
Who got what? How long had they kept us? Had anyone actually bought a timeshare?
It was quite the little traveling support group.
As for us, we had two birthday dinners to finance and absolutely no timeshares to worry about.
Mission accomplished.
The sales team was more aggressive with Sis. She reported being a little tempted – fortunately, that was only a momentary lapse.
Boudros Birthday Celebration
After surviving an afternoon of timeshare theatrics, it was time for something considerably more civilized.
My birthday dinner!
Sis treated me to dinner at Boudro’s, a lovely restaurant along the River Walk. We settled into a cozy table inside, surrounded by rustic wood furnishings and an eclectic collection of vintage mirrors.
We both enjoyed halibut with mashed potatoes and vegetables, accompanied by a glass of wine.
Dinner was delicious, but the real indulgence came with dessert. Sis celebrated my birthday with creme brûlée.
My double brownie was ridiculously decadent — rich chocolate, melting ice cream, and enough chocolate sauce to make a nutritionist wince.
Walking, Wandering, and Occasionally Getting Lost
Between our unexpected adventures, we actually did what we’d come to San Antonio to do.
We got outdoors.
We explored.
The River Walk is a beautiful network of pathways winding along the San Antonio River, with restaurants, bridges, gardens, and inviting places to stop and simply enjoy the atmosphere.
The weather was gorgeous — warm and a little humid, with gentle evening breezes. Shorts and short sleeves were comfortable day and night.
Our routine was simple. Breakfast, a morning of exploring, lunch, back to the hotel for a rest, and out again in the evening for dinner and more exploring.
We occasionally got lost, especially when I was leading. Why anyone lets me lead is truly surprising.
Finding our way back to the hotel became something of a recurring challenge.
Eventually, we figured it out.
We were tracking our mileage, and by the end of our four-day adventure, I had logged 27.59 miles.
Who knew a birthday vacation could double as endurance training?
There’s something special about discovering how much fun being active can be when you’re enjoying the journey rather than concentrating on the exercise.
An Unexpected Celebration: Día de los Muertos
When I’d booked this trip months earlier, I had no idea the final evening would coincide with San Antonio’s Día de los Muertos river parade.
That turned into its own little adventure to find a last-minute seat and a festive clothing option.
Elaborately decorated boats would travel along the River Walk, illuminated with colorful lights, skeletons, and music to celebrate the Mexican tradition of honoring loved ones who have passed.
We initially purchased two parade seats online when an additional seating section became available.
We went looking for our assigned seats, C29 and C30. They were way down at the beginning of the parade route.
Getting there involved a considerable hike. Access points along the River Walk would be restricted, and ticket holders were required to enter through designated gates.
That sounded increasingly complicated for two folding chairs.
Besides, there weren’t any restaurants near the beginning of the parade route, and we were looking forward to steak for Sis’s birthday dinner.
So, we abandoned our seats and went looking for a steakhouse.
And that’s when we stumbled upon Lone Star Cafe, conveniently located along the River Walk, not far from our hotel.
We met Celine and her manager, Charlie, appropriately dressed in a skeleton shirt. He offered us a table for two overlooking the river. Parade seating was $10 per person with dinner.
We would arrive at 5:30 for dinner and remain at our riverside table for the parade.
Once the logistics were solved, we decided the occasion called for appropriate attire.
My sister selected a white shirt with a glittering skeleton design.
I chose a purple colored shirt with sparkling skull designs on both sides.
Festive, comfortable, and just irreverent enough for two sisters who’d already survived Dick’s Last Resort.
We paired them with jeans and headed out for the evening.
We settled into our riverside table with iced tea before ordering ribeye steaks, mashed potatoes, and salad. I enjoyed a glass of Pinot Noir while Sis celebrated with a margarita.
And because no birthday dinner is complete without dessert, I indulged in another brownie while Sis ordered a slice of cheesecake.
Around 8:30, the illuminated parade boats began passing directly in front of us.
Colorful lights reflected on the water. Skeletons glowed against the evening sky. Beautifully decorated boats floated past to lively music, creating a festive atmosphere along the entire River Walk.
As if the parade weren’t entertaining enough, Lone Star Cafe happened to be right next door to Dick’s Last Resort.
Between the illuminated parade boats, we entertained ourselves by watching the conehead activity next door.
Apparently, we’d come full circle. But this time, I was perfectly happy to enjoy the hats from a safe distance.
In honesty, I couldn’t have imagined a more enjoyable way to spend our final evening in San Antonio.
More Than Another Destination
Over the years, I’ve discovered that traveling solo can be wonderfully liberating. I enjoy setting my own schedule, exploring at my own pace, and following my curiosity wherever it leads.
But there’s something equally wonderful about sharing those discoveries with family.
Laughing together when you wander into the wrong restaurant.
Exchanging conspiratorial glances when you’re on a covert mission.
Understanding why a spontaneous purchase of matching holiday-themed T-shirts is absolutely necessary.
And sitting side-by-side when the lights of an unexpected parade begin dancing across the water.
Our San Antonio birthday getaway was filled with lovely surprises, ridiculous moments, delicious meals, and plenty of laughter.
We crossed another destination off my growing bucket list.
But the best part wasn’t the destination.
It was spending time with my sister.
When she left early Saturday morning for her flight home, I missed her almost immediately.
And that, I think, says everything.
Some adventures are wonderful because of where you go.
Others become unforgettable because of who shares them with you.
San Antonio gave us both.
