
An original co-founder of designtripper (who left to renovate and run this), Kelly recently got back from Puerto Rico, where she and her family stayed in a series of noteworthy places–an artist’s apartment and courtyard in Viejo, a remote house in lush Culebra, and finally, the storied Gallery Inn on their way out of town. Set in a 300-year-old colonial mansion in Old San Juan, this 22-room hotel is 23,000 square feet of old black-and-white tiles, stone floors, grand archways, hidden gardens and trickling fountains. Equestrian enthusiast owners Manuco and Jan–the latter also an esteemed local artist–have decorated with interesting layers of photos of horses, textiles, screen-printing, statues and art.
We particularly love the disclaimer on their site: “We would never want to see our place turn into the bland, cookie-cutter sort. We must warn you! Our inn is over 300 years old, and we feel that the essence of authenticity and beauty is of utmost importance and value to our concept. We do not have any elevators, and never will. If you cannot take staircases, this might not be the hotel for you. Our exotic birds are absolutely precious to look at, but they will occasionally screech. If you feel this would bother you significantly, we might not be your best choice. Also, we are not secluded from the local population, so if you are the kind of traveler who wants to feel “protected” from the locals, you should not come.”
They should also add that if you’re open to beautiful, eccentric spaces full of character, charm, and yes, beautiful, imperfect flaws, then you’ll probably love it here. Major bonuses: the best rooftop deck in town and this cool beach house a few blocks away, where you can do your own bbq-ing and hang out seaside.








[Photos by Kelly Flamos, except mask image by William Bay Photography via flickr and dining room via Uncommon Caribbean]