3 DAYS IN SAN MIGUEL WITH ROBBY

3 Days in San Miguel de Allende with My Dad

Some trips are about discovering a place for the first time. Others are about seeing it again...through someone else’s memories.

This trip to San Miguel de Allende was special because I experienced it with my Dad, Robby, whose first visit to San Miguel was in 1961. Long before the city became an internationally known destination, he had already wandered these same cobblestone streets.

Over three days, we ate, walked, and explored our way through town... mixing some of my favorite spots with the stories and perspectives of someone who knew San Miguel decades ago.

Here’s how we spent a perfect long weekend together.

Day One: Arriving in San Miguel

There’s something magical about arriving in San Miguel de Allende. The streets narrow, the colors get brighter, and suddenly everything slows down.

We started the evening with sunset drinks at Luna Bar, a relaxed way to settle into the rhythm of the city.

For dinner, we headed to The Restaurant, a longtime favorite tucked inside a beautiful courtyard. It felt like the perfect first night: good food, great conversation, and a reminder that some of the best parts of travel are simply lingering over dinner.

Day Two: Walking the City

One of the best ways to experience San Miguel is on foot, so we started the day with a walk to brunch at Villa Santa Monica. Hidden behind stone walls, the gardens feel like a secret oasis. This is the oldest B and B in town, and we call it "The Peacock Place"...they have peacocks roaming the gardens in the back. Don't forget to take a pic sitting on the fountain, a 27-year-old running tradition in our family. 

After brunch, we wandered over to Rosewood San Miguel de Allende via El Parque Juarez to stroll the grounds and take in the view of the city.

It’s hard to imagine what San Miguel looked like when my dad first visited in the early ’60s...long before boutique hotels and rooftop bars...but hearing his stories while walking these streets made the city feel even more layered with history.

Art, Markets, and the Heart of Town

Later that morning, we grabbed a taxi to La Fábrica La Aurora, a former textile factory that’s now filled with galleries and studios. It’s one of my favorite places to wander because every corner holds something unexpected.

From there, we walked toward the Mercado de Artesanías, stopping along the way to browse shops and watch daily life unfold.

Eventually, we made our way to the center of town and stepped inside the iconic Parroquia de San Miguel Arcángel, whose pink spires tower over the plaza.

Before dinner, we stopped at Atrio for margaritas on the rooftop. Sitting there with my dad, looking out at the Parroquia, it was easy to imagine the decades of visitors who have paused in that same spot.

Dinner with a View

Dinner that night was at La Posadita, one of the city’s classic terrace restaurants. As the sun went down and the lights came on across the rooftops, the whole city seemed to glow.

We finished the evening with a nightcap at The Blue Bar, swapping stories and soaking up the lively energy of San Miguel at night.

Day Three: Wine Country and a Slow Goodbye

On our last day, we headed just outside the city to Dos Búhos Vineyard for wine tasting and lunch. The countryside was a peaceful contrast to the bustle of the historic center.

Afterward, we wandered back through town, enjoying the kind of unplanned moments that make San Miguel so special...ducking into shops, stopping for coffee, and simply taking in the streets.

Before leaving, we had one last meal: sourdough pizza, Bennu, and Hot Chocolate and Churros from San Augustin. 

Why This Trip Meant So Much

Traveling with my dad in a place he first experienced more than sixty years ago gave the trip a deeper meaning.

San Miguel has grown and changed over the decades, but its magic is still the same: beautiful architecture, incredible food, and a pace of life that invites you to slow down.

For me, these three days weren’t just about visiting San Miguel de Allende.

They were about sharing it.