The Gallery Inn

"Old San Juan is known for its atmospheric and historic hotels, but none quite match the Gallery Inn for personality and creativity. Composed of six intertwined town houses, this endlessly fascinating hotel beckons guests to wander through its nine interior gardens and patios, and seven parlors and porticos. Dating to the mid-1700s, the oldest building, La Cueva Del Indio, is located above Old San Juan’s north walls, meaning the views out to sea are the same ones that captivated the conquistadors. Owner Jan D’Esopo, is a well-known sculptor and her works dot the hotel’s meandering interior, which has enough comforts and homey character to avoid feeling like a museum. Equally unique are the 25 rooms, decorated with everything from silk screens and watercolors to sculptures and paintings. Some even feature elegant, four-poster beds and balconies with views of the ocean. Just don’t expect to watch TV—one, there are no TVs, and two, the views out over the old fortress walls are better than anything on Netflix."

"An art gallery, studio, and boutique hotel rolled into one, The Gallery Inn is full of paintings, bronzed statues, and intriguing ephemera fashioned by artist and lady of the manor, Jan D’Esopo, who discovered the long lost building in 1961. The onsite Cannon Club has a candlelit concert series with dueling jazz pianos (where you can catch a descendant of the D’Esopo family, Nico, joining in on his violin). Live parrots nibbling on mint leaves grace various perches throughout the space.It’s a total fantasy and the room decor reflects this. Heavy wine-colored drapes and gold details, along with lush tropical greenery, hold court in the 27 rooms."

"Old San Juan is known for its atmospheric and historic hotels, but none matches the Gallery Inn for personality and creativity. Composed of six intertwined town houses, this fascinating hotel beckons guests to wander through its nine interior gardens and patios and seven parlors and porticos. Dating to the mid-1700s, the oldest building, La Cueva Del Indio, is located above Old San Juan’s north walls, meaning the views out to sea are the same ones that captivated the conquistadors. Owner Jan D’Esopo is a well-known sculptor and her works dot the hotel’s meandering interior, which has enough comforts and homey character to avoid feeling like a museum. Equally unique are the 25 rooms, decorated with everything from silk screens and watercolors to sculptures and paintings. Some feature elegant four-poster beds and balconies with views of the ocean. Just don’t expect to watch TV—one, there are no TVs, and two, the views out over the old fortress walls are better than anything on Netflix." - AFAR Editors