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Story and photos by Reb Stevenson
“Hello!”
The greeting at The Gallery Inn in Old San Juan, Puerto Rico, is prompt and friendly.
And it is delivered by a parrot.
The parrots – four in all – practically outnumber the human staff . One of them has been designated “social director” and even has its own business card.
That’s just the first clue that this otherworldly hotel is practically manufacturing eccentricity.
The second clue is that when I check in, the receptionist fumbles around, looks disoriented and admits that he doesn’t know where my room is.
In fact, he doesn’t seem to know much about the place at all. He mentions that there is a rooftop terrace – the highest in Old San Juan – but he doesn’t know how to get there, either.
The Gallery Inn in San Juan, Puerto Rico
But somehow, the confusion only adds to the tone of the hotel, a tone I’d call “enchanted chaos.”
An amalgamation of six homes – some of them dating back to the 18
th century – The Gallery Inn is one crazy woman’s magnum opus. And it is, quite simply, wonderful.
Her name is Jan D’Esopo. She’s away when I visit. Of course, her absence only thickens the plot. Now she has taken on a magical quality like an invisible fairy godmother, and her disembodied presence lingers in the tapestries, her voice resonates through the omnipresent trickling fountains.
The Gallery Inn In San Juan, Puerto Rico

In 1961, D’Esopo and her partner, Manuco Gandia, both artists, opened The Gallery Inn. True to the name, they filled it from floor to ceiling with their own whimsical art.
“Anything that you see on the wall is made by the owner,” says manager Frances Otiono.
Bizarre statues and busts abound: a triad of horse heads on stakes, a toddler perched in an alcove, dour men in suits and ties. 
Awestruck, I attempt to absorb the explosion of creativity. D’Esopo has given birth to an escapist’s Eden, the kind of place in which you could willfully incarcerate yourself for a week. There are courtyards that ooze plants (19 gardens and courtyards in all), overflowing bookshelves and welcoming chairs in which to take advantage of both.
Common areas like an outdoor living room and a “dollhouse” room provide further refuge. A highlight is the sumptuously decorated music room, where guests are invited to tickle the ivories on the nine-foot grand concert Steinway piano.
“Who
is this magnificent woman?” I babble more than once, even after I’ve heard the answer.
“She’s 74 but her energy is like she’s 24 years old,” says Otiono. “Her mind is running a hundred thousand miles an hour.”
Otiono explains that, like many artists, her boss has a knack for starting one project and then getting distracted by another.
“But somehow, it all turns out.”
The music room at The Gallery Inn in San Juan, Puerto Rico
Each of the 22 rooms is completely unique and full of European charm. Some have canopy beds. Some have Jacuzzis. The best have their own terraces that overlook the sea. All are densely packed with art.
Downstairs, Otiono reveals a cluster of romantic dinner tables, set with clay plates depicting nude women. These are, of course, handmade by D’Esopo.
“Sometimes we’ll make dinner for guests on a whim,” explains Otiono.
That night, I venture out into the seven square blocks that constitute Old San Juan. Lively, friendly, and graced with colourful Spanish colonial architecture, it is a destination unto itself, regardless of the sun, sand and surf factor.
The air is sticky, and a stint at a salsa club leaves me feeling like fly paper. When I get back to The Gallery Inn, it’s past midnight.
“I don’t suppose the pool is…” I ask the night attendant.
“Yes, of course it is!” he cuts in.
I glide into the lit turquoise waters. Like everything at the hotel, the pool is not straightforward. It’s more like two lanes, separated by a crumbling old brick wall. Refracted light illuminates more of D’Esopo’s statues, my only company in the courtyard.
To top it off, classical music emanates from a hidden speaker. The experience is thrilling, like stealing a moment from the fantasy realm.
“Who
is this magnificent woman?” I think. Again.
Upon leaving, I take her business card, intending to call for a follow-up interview.
But I never do.
The Gallery Inn is an ode to imagination. It’s best left that way.
                                                                       
The Gallery Inn in San Juan, Puerto Rico
IF YOU GO
The Gallery Inn
www.thegalleryinn.com
(787) 722-1808
From $175US to $350US per night
Extras: Wine and cheese reception every evening