The imposing yellow building rises from the Plaza de la Catedral, a five-story converted convent that was home to nuns for 252 years before becoming a flophouse that Robert Frederic Woolworth (yep, that Woolworth) began remodeling in 1959. El Convento Hotel opened in 1962; in the 1990s and early 2000s, it was remodeled—and surreptitiously renamed Hotel El Convento.

The next best thing about the 58-room property is the outdoor space, excellent for those 80-degree-average tropical temperatures. A tiled open-air courtyard is shaded with palm trees and brings to mind the South of France—until you order the killer pork tacos from the restaurant, and are rapidly transported back to the Caribbean. A daily wine and cheese reception doesn’t necessarily sound like a rolicking time, but sipping free vino from the roof deck (complete with pool and hot tub) overlooking San Juan Bay is an ideal way to kick off an evening of fine dining or bar hopping.

There are plenty of other things to enjoy here: the Spanish Colonial architecture, which makes you feel a part of the old city; a second restaurant which serves traditional tapas so you can stay in for a night without feeling guilty about missing out on local culture; and spacious rooms with Juliet balconies. A cat named Trixie calls the hotel home, and with rooms starting at $165, you can too—at least for a little while.