The Art of Hospitality: The Dolan Family Welcomes You To Their San Miguel Life

As one of San Miguel’s true connectors, Ann Dolan — together with her husband, Jim, and their three children — has spent nearly three decades welcoming people into their world and into the San Miguel community. Whether they’re hosting friends at their ranch, welcoming clients to town, or championing the city abroad, their gracious hospitality has become part of San Miguel’s story itself.

Olivia, Ann, Jake, Sofía and Jim Dolan

There’s something about San Miguel that makes hospitality feel effortless. There’s a natural ease here—whether you’re meeting first-time visitors or welcoming old friends back for the season, the energy is always electric. In San Miguel, mi casa es tu casa isn’t a phrase — it’s our way of life.

For my husband Jim and me, and our children, hospitality has always been part of our rhythm. We entertain on some scale several times a week—friends who live here year-round, visitors returning for the season, or clients curious about making San Miguel home. But it’s never “entertaining” in the formal sense; it’s simply how life unfolds here. It’s easy, natural, and fun. As one of my girlfriends said, our parties are never structured—we go with the flow. Sometimes Jim is behind the grill, sometimes a friend, and sometimes even a bartender, depending on the size of the group.

Where hospitality lives — the Dolans’ terrace, always buzzing with friends, family, and new stories in the making.

A Life Built on Adventure and Connection

When Jim and I married, we made a commitment to live a life of adventure—with no regrets. We knew instinctively that we’d one day live in another country, learn another language, and own our own company. We just assumed the military would take us to Germany, that we’d learn German, and that I’d sell Mary Kay products! It sounds funny now, but that seed of adventure was what shaped our path. We wanted a life filled with purpose, with no looking back, wondering what could have been.

Back in our military days, our friends affectionately called our home The Dolan Diner. Even then, we loved spontaneous dinners and long evenings filled with conversation. That same instinct found its perfect home here in San Miguel, where every meal becomes an experience—whether planned or impromptu. We’ve fully embraced the tradition of comida: long, lingering afternoons filled with conversation, laughter, and often, the sound of mariachi music drifting through the garden.

Sometimes I have to remind myself that what feels normal to us—an afternoon meal that stretches late into the night—feels utterly magical to our guests.

Friendship on Horseback

Jim loves riding horses, and over time, that’s become one of our favorite ways to connect with others. Horses and nature have a way of bringing people together—you can slide in and out of conversations, reflect, and appreciate the beauty around you. One of Jim’s first questions to anyone new is often, “Would you all like to go for a horseback ride?” That simple invitation has started countless friendships.

Once someone says “yes,” I already know what’s next—I pull a brisket, chicken, or ribs from the freezer and start planning lunch. I’ll think of who to invite to complement our new friends, so they can begin creating their own San Miguel circle. The day of the ride, Jim’s at the outdoor kitchen preparing the meat, and by the time the riders return, the scent of smoked barbecue fills the air. We toss quesadillas on the grill, open some wine, and the afternoon begins. Before long, there’s laughter, new connections, and that familiar San Miguel magic that always seems to appear when good food and good people come together.

Those are the moments that define this place—spontaneous, genuine, shared. That is quintessential San Miguel.

The Spirit of Community

Trying to capture what life feels like here —what we experience week after week —is nearly impossible unless you’ve lived it. This town is deeply welcoming. Writing this reminded me of the countless friendships formed around long lunches, shared causes, hobbies, dinners, and celebrations. For newcomers, getting involved — whether through local charities, art openings, community events, or simply saying yes to invitations — is one of the best ways to find your place here. For those of us who’ve been here for decades, it’s what keeps life vibrant.

Over the years, our gatherings have taken many forms: ranch parties with live music and dancing, reunions with friends for an afternoon grill, a taco truck after a six-hour trail ride through the mountains, smaller dinners for twelve, birthday celebrations, and our annual Thanksgiving feast—where there’s always an extra seat at the table. For me, hospitality isn’t about perfection; it’s about connection. It’s about creating a space where people feel comfortable, happy, and maybe even a little inspired.

The holidays at the Dolans' — where the doors are open, the table is full, and every guest feels like family.

A Life Measured in Moments

Last year, we hosted what we called “The Generational Party” on January 2nd. It was one of my favorite gatherings ever. We invited friends we’ve known for over twenty-five years—many of whom are now grandparents—with their grown children and new little ones. Watching toddlers ride our pony “Bella” and realizing that we’d been part of these families’ stories for decades was incredibly moving. In that moment, I thought, Wow, look at what we’ve lived, shared, and built together here in San Miguel.

This August, Jim and I celebrated our 60^th birthdays and our 35th wedding anniversary with a two-day event that our children planned for us. The first day included a trail ride for 70 riders, roasted pigs, mariachis, an opera singer, and, later, banda music—traditional charro (cowboy) music that had everyone dancing. The next day, we had a seated lunch for 120 guests—different groups of friends from different chapters of our lives here and abroad. It was pure joy.

The Dolan Five

After 30 years in San Miguel, we still feel deep gratitude for this life—the friendships, the culture, our community involvement, and the chance to be ambassadors for this incredible city. Through our work and our travels, we’ve had opportunities to share San Miguel’s story with people around the world.

A City That Welcomes the World

When Jim and I first arrived, San Miguel was still a hidden gem—beloved by artists and dreamers, but far from the global destination it is today. Together, we’ve witnessed its evolution and are proud to have played a small part in shaping it through our work in real estate.

What we truly offer, though, goes beyond homes—it’s a sense of welcome, a bridge between worlds.

Just this week, what started as a few casual introductions turned into a full-blown gathering. We had several different commitments on Friday—meeting couples from Austin, Dallas, Houston, and San Antonio. He knew all the couples but one. One conversation led to another, and before the afternoon was over, plans for a lunch at our home had been made.

By Sunday, the guest list had somehow grown to fourteen. The ribs were thawing, the table was set, and a spontaneous meal among strangers was ready to unfold. None of the couples knew each other before that Friday but by Sunday, they’ll all be riding horses together, dining on ribs and chicken and celebrating the Day of the Dead and new friendships.

It’s confusing to explain, but that’s exactly the point. That’s San Miguel. Connections happen naturally here, friendships form overnight, and life has a way of weaving stories together before you even realize it.

That’s the San Miguel I love—and the spirit I try to share, one gathering, one introduction, one heartfelt conversation (and sometimes one very spontaneous lunch) at a time.