How I Choose Places

I was 26 years old, in between jobs, trying to figure out my direction, and standing at a quiet crossroads when friends invited me to join them on a road trip through Costa Rica. I came into the group as a guest — I needed to get out of New York for a moment, reset, and have an adventure. And that’s exactly what it was.

Our first destination was the most remote. After landing in San José, we boarded a small propeller plane, followed by an hour-long drive on bumpy, unpaved dirt roads. Eventually, we arrived in the small beach town of Santa Teresa.

We stayed at Florblanca, which was the nicest place we were at on that trip — and even then, we all shared a room. Everything else was far more rustic. What made it special wasn’t the luxury, but the setting: an untouched stretch of beach, quiet rock formations, and the feeling of being far removed from anything performative. I learned to surf there, watched glow-in-the-dark plankton shimmer at night, and explored the simplicity of the town. It was the first time in a long while that my body felt curious instead of braced.

Over the next ten years, I returned several times. Santa Teresa became a place many friends gravitated toward as well, and our travels would sometimes overlap. There was a familiarity each time I arrived — a sense of rhythm that made it easy to settle back in.

One constant thread through those visits was Stefano, the infamous yoga teacher. I took his class the first time and continued to practice with him whenever I returned. His teaching became part of how I experienced the place — grounded, challenging, unpretentious.

I’ve thought a lot about why Santa Teresa keeps calling me back. It isn’t about a moment in time or a version of myself — it’s about what the place consistently offers. A sense of community. Space for self-exploration. A lifestyle built around movement, nourishment, and simplicity. Clean food. Yoga and Pilates. Surfing. Time outdoors. Fewer distractions, fewer decisions, and more room to listen. Each time I return, those elements create the same invitation: to slow down, to come back into the body, and to remember how little is actually needed to feel well.

This time, the timing wasn’t perfect. Life in New York was intense and full, and under normal circumstances I probably would have canceled. I hadn’t done anything like this in ages. But something in me knew I needed a gentler re-entry — not an escape, not a disruption, but movement. Going to Santa Teresa to see friends, to support Julie as she opened her studio, and to show up for something communal rather than transactional felt like the right way back.

After COVID, several close friends had moved there. Julie had just opened her Pilates studio, This Way Movement, and invited me to do a trunk show for Live The Process. My childhood best friend Linda was living there now too, having opened the most beautiful restaurant, Doki Doki. Shani, who once taught at our New York studio, had relocated as well — teaching, creating ceramics, DJing, and living with a kind of creative freedom that felt deeply aligned.

I arrived late at night in the middle of a torrential rainstorm. I stayed at the home of a friend-of-a-friend we had met only briefly before. Her house sat right near Rocamar, directly on the beach. I couldn’t wait to wake up to the ocean.

Linda picked me up on a quad — the main form of transportation there — and we went to her friend’s restaurant for dinner. Seeing her embrace this slower, simpler lifestyle felt worlds away from her former city-girl reality. The fish was incredibly fresh, everything locally caught, paired with a thoughtful selection of natural wine. It was a special way to begin a packed week.

Over the following days, Linda showed me the local rhythm: herbal apothecaries, produce stands, and what she jokingly called the “Erewhon of Santa Teresa,” except this was the real thing. I drank fresh coconut water straight from the shell, ate the simplest, freshest food, and met people who had relocated there in search of a quieter way of living.

There had been a noticeable influx of change post-COVID. I met women who had moved from Los Angeles and New York — creative producers, restaurant founders, mothers — each choosing a different pace. One afternoon we met at Tropico Latino right on the beach, sharing papaya smoothies and conversation.

I spent time at Julie’s studio, taking a Reformer class and helping her get organized. The space itself stood out as you drove by — thoughtful, intentional, and unexpected.

Florblanca had since been sold, but Stefano was now teaching at Nantipa, a wellness sanctuary nearby. After the trunk show, I returned there for sunset ceviche, watching the light change over the water.

For the second half of the trip, I stayed in Mal País, just beyond Santa Teresa. Shani had moved into a home deep in the jungle — quiet, remote, surrounded by green. Getting anywhere meant riding a quad up winding roads.

She took me to Montezuma, a place I had somehow never visited before. It felt mystical and untouched. We had lunch at Playa de los Artistas — Italian-inspired and seafood-forward, set right on the beach — sharing plates slowly. The simplicity of it all felt intentional.

The trunk show itself became a beautiful gathering of local community. There was jewelry-making, homemade hibiscus tea, tahini, ginger cookies, and a functional medicine doctor offering antioxidant testing and lifestyle guidance rooted in regenerative health. It felt aligned, generous, and grounded.

My final night included dinner at Bajo El Arbol, a Spanish-inspired spot with incredible tapas, followed by a night at Goma — a speakeasy above a local market where Shani was DJing. It could have been Berlin, Paris, or New York — and yet it was unmistakably Santa Teresa.

I know the recharged feeling won’t last forever. So I’m being intentional about what comes next. This trip reminded me that when travel is approached with care, it doesn’t pull you away from your life — it helps you return to it with more clarity.

What follows is a guide to Santa Teresa — the places, rhythms, and practices that keep calling me back.

The guide below is available to paid subscribers.