Dropping everything to move to the Caribbean and run a resort sounds like a dream come true. But in practice, that experience can be riddled with roadblocks and pitfalls.

In her series of “Peer to Pier” interviews, Meg Pier sat down with Steven Weingarten, a New York attorney-turned-owner of Casa Grande Mountain Retreat in Puerto Rico.

Read on to learn about his process of transitioning from high-stress city living to running an eco-lodge and yoga center in the mountains of Utuado.

Meg Pier: Can you describe the trip to Puerto Rico when you decided to buy Casa Grande?

Steven Weingarten: I lived in Sea Cliff, New York, in a charming carpenter gothic home overlooking Long Island Sound. I was more or less content—not looking for nor thinking about a major lifestyle change. It was mid-November and I was in my Great Neck law office gazing out at the snow. I said to myself “I need a winter vacation.”

I immediately thought of the tropics and then remembered Puerto Rico where I had worked at a travel camp in the hills of Bayamon for couple weeks one summer back in the late 1960s. I went to the library for some guidebooks and discovered the fact that Puerto Rico had an extensive mountain range. I thought it would be interesting to split the vacation between beach and mountains so I checked the possibilities in the central mountains. There were three: Hacienda Gripiñas, Hacienda Juanita and Casa Grande. The trip was planned for Christmas week and Gripiñas and Juanita were full.
I had to call Casa Grande four or five times before I got through to someone who didn’t hang up the phone on me and who spoke English.

MP: Tell me about your first visit to the property.

SW: The place was down and out. Shabby bedding, musty carpeting, poor lighting, tiles falling off the bathroom walls. The swimming pool water was dark green and there were no chairs or lounges to sit on. There were hooks on the balcony posts for hammocks but no hammocks! The place was stale and lacked respect and love for itself.

During the four days there, my wife Marlene and I started thinking about possibilities. She was a court stenographer back home but her career was on the wane as she had carpel tunnel syndrome. She was an excellent cook and we both thought she could run the restaurant. With my business skills as a lawyer and my passion for transforming space, decorating and design I thought I could handle the rest. Somehow the staff picked up on our interest in the place and began to encourage us. One thing led to another and by the time we arrived at [our next destination] I was at the desk writing a letter to Casa Grande’s owner.

For another relaxing spot in Puerto Rico, check out: The American Caribbean: Culebra, Puerto Rico Travel Guide

MP: After buying the property, you were back and forth between the locales for a while, a foot in two worlds. What was that like?

SW: It was extremely difficult to transition from one to the other and back again, almost like throwing a switch on my mental, physical and emotional states. I did that for five years and then pulled the plug on life in New York.

MP: Despite your friends telling you that you’d miss things like Broadway plays, and that the change was sometimes a little scary, you said you never felt like you were making a mistake. Can you describe that sense of certainty?

SW: Anxiety, worry and fear show up for me in my belly. When things aren’t quite right I’ll get an ache or churning feeling in my gut. That never happened during the decision-making process.

MP: You draw a parallel between being a lawyer and now being in the hospitality business, pointing out that both are service industries. Can you talk about the similarities and differences of the two professions?

SW: Both professions provide services; the lawyer, legal advice and advocacy and the hotelier, room and board. Of course law is brainy and maybe a little stuffy while hotel work is almost intimate as we’re dealing with providing for the very basic needs of the guest; namely, food and shelter.

MP: How did that move affect your personal life?

SW: When embarking on a new life, all the issues in our relationship seemed to take center stage. There was no more hiding or pretending. We had to face up to our shortcomings and our differences. It resulted in the divorce and my subsequent buyout of her interest in Casa Grande.

MP: Tell me about the two-year period in which you lived in Room #8 before moving into your home.

SW: It was a transition time from married life in a house to single life in a hotel room. It wasn’t fun. I was always at work. I’d go to bed wondering if the guests had enough hot water or any water at all. I could hear guests making noise in the night and wondered if others were being disturbed. I was on call 24/7. Not that I’m not on call now 24/7 but it’s different.

MP: Tell me what specifically it is that you enjoy about transforming spaces, in the context of Casa Grande.

SW: In my earlier years I rented five different apartments and put my hands to them all. Then I moved up to homeownership and loved outdoor landscaping and gardening and the interior work as well; painting, wallpapering, woodworking, color selecting, window treatments, the whole nine yards, I loved it all. While at Casa Grande I observed its sorry state and how needy it was. I knew from my experience that I could touch it and make it sparkle, like polishing a gem. That’s pretty much what’s happened here. It’s a jewel now.

Thought about just picking up and moving to a quiet Caribbean island? Find out what it’s like with: Moving To Paradise: Life In The U.S. Virgin Islands

MP: There is a temple on site at Casa Grande and you are a certified yoga instructor. Can you describe how that practice developed?

SW: I discovered yoga 23 years ago when I stopped in at a storefront ballet studio to take a yoga class. The class ended around 4 p. m. I walked home and lay down and had the most blissful sleep ever. I thought there must be something to this discipline. I started taking classes here and there and ended up at Kripalu Center for Yoga and Health in the Berkshires. Then I began practicing regularly. But I wasn’t consistent with it. However, I found that when my life wasn’t going well I’d return to the mat. I started teaching at Casa Grande in 2001 although I hadn’t been certified. Basically, I shared what I knew. In 2007 I completed a 200 hour Kripalu certification and am now halfway through the 500 program.

MP: You shared with me a quote from Plato: “Be kind, for everyone you meet is fighting a hard battle.” Can you tell me about the meaning of this quote for you?

SW: Sometimes people show up at the front desk in a troubled state and their unhappiness is quite evident. I make an effort not to take that personally. I breathe deeply to empathize with them and do what I can to make them feel better.

MP: Even though you work in paradise, that doesn’t mean you don’t face challenges. Can you comment on those periods and what sustained you?

SW: Hurricane George closed us down for two months and when we re-opened it took some time to get back on course. Then really hard times hit us in 2005 and I wondered how long I could the carry the place without folding. This happened more than once. I had many sleepless nights full of worry. But I rode the wave each time and each time I came through it to move forward. I carried with me the strong belief that what I was doing had real value for people; that people yearned for peace and quiet and that it was not readily available. It was my intention to meet that need.

MP: Can you elaborate on your long-term versus short-term goals?

SW: When I bought the place I had a very limited goal, which was to just see if I could run it. Neither I nor my wife had been in this business so we were starting off behind the eight ball. We were completely beholden to the staff. They ran the place by default. Gradually I became more knowledgeable and slowly but surely started to assume more authority. I made a lot of mistakes along the way in all areas. But most of those mistakes I’ve only made once. Now I feel like I’m fine-tuning the operation. I can’t imagine doing anything else anywhere else. I feel complete.

By Meg Pier for PeterGreenberg.com. Meg Pier is a travel writer for the Boston Globe and other publications. Visit her on the Web atwww.ViewFromthePier.com.

Related links on PeterGreenberg.com:

• Peer to Pier: Claudia Scholler of Spanish Eco-Lodge Cortijo El Saltador
• Peer to Pier: Charles McDairmid of Vancouver Island’s Wickaninnish Inn
• Peer to Pier: Lucy Fleming on Eco-Travel and Belize Jungles
• Eco-Travel section
• Peer to Pier: Armenia Tree Project, Interview With Anahit Gharibyan
• Peer to Pier: UN Foundation CEO Kathy Calvin
• Peer to Pier: Global Heritage Fund Co-Founder Talks Sustainable Tourism
• Peer to Pier: Interview With Hitesh Mehta, Eco-Tourism Pioneer

Puerto Rico Travel Links on PeterGreenberg.com:

• The American Caribbean: Culebra, Puerto Rico Travel Guide
• Off The Brochure Travel Guide: San Juan, Puerto Rico
• Ask the Locals Travel Guide: Puerto Rico
• Puerto Rican Music, Culture, Arts & Festivals – PGW Radio
• Puerto Rican Flavor With Chef Wilo Benet – PGW Radio
• Puerto Rico’s El Yunque Rainforest – PGW Radio
• Moving To Paradise: Life In The U.S. Virgin Islands
• Travel Tip: Finding The Right Island Vacation
• America’s Gypsy: Puerto Rico In Chicago
• Caribbean Travel section