How a boomer ends up on an island paradise

Baby boomer Steven Weingarten lives in Puerto Rico. Why? Well, that’s his story.

Many people fantasize about picking up stakes and moving to a tropical island to run a small hotel. I’m not one of those people. I’ve never had such a dream.

Steven Weingarten

Steven Weingarten

But here’s the reality. It’s 4 pm on a gloomy November afternoon in 1995 and I’m gazing out the window of my Great Neck, Long Island law office watching the large snow flakes float towards the cold concrete below. I feel the chill in my bones and the need to get warm soon. I go to the library (remember those?) and bring home a bunch of guidebooks to study. To my surprise I learn that Puerto Rico has a central mountain chain in addition to its famed beaches.

The first stop on the trip is a four night stay at Parador Casa Grande, a 20 room hideaway in the heart of the Cordillera Central. The two hour drive from the San Juan airport in a rental car is challenging and arduous. The mountain roads are narrow and the local drivers too adventurous and daring. But the weather is ideal and I’m looking forward to practicing my rusty Spanish that I haven’t used since high school.

We arrive at dusk and to our surprise the place has few guests staying on Christmas Eve. It soon becomes apparent why.


The place is in serious disrepair. The water in the swimming pool is a dark soupy green. There are no chairs, lounges, or umbrellas in sight. I bring a towel from my room to lie down on next to the pool. The bedroom floor has wall-to-wall carpeting (not a good idea in a super-humid, hot, sticky environment) and the bedclothes have a nubby, sandy feeling. The tiles are falling off the bathroom walls and the tubs are badly stained and rusted. The tiny sink is screwed to the wall and its intestines are in plain sight below. The towels are threadbare and rough to the feel. The hacienda, the main house, is no better, being dimly lit in the evening with soiled and rickety furniture. The place wreaks of neglect.



For some reason the staff starts talking it up with me and giving me the lowdown. Their payroll checks are bouncing regularly. The owner hasn’t been making room tax payments to the local treasury department for years. Payroll taxes are due to the IRS and foreclosure is imminent. The front desk manager shows me the reservations book and at one point bursts out, “You know you really should buy this place!” I’m a bit startled by the suggestion but inhale it anyway.

Days later when we arrive at our final stop on the trip at an elegant beach resort on the west coast of the island, I corner the owner and tell him I’m considering buying a small hotel in the central mountains and ask him if he thinks I’m crazy. “I don’t think you’re crazy but you’re in for a lot of work,” he answers.

Twenty years later, I’m still here, living a dream I never had.

Learn more … click here.

1 Comment

  1. Fascinating! And congrats for taking such a big leap into the unknown. I urge everyone to click the “read more” button at the end (I did) and learn more about Steven – fantastic, how brave you are and well done, Casa Grande looks like anyone’s dream place for a true vacation!

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