Courtesy of Gallery Inn

Puerto Rico: Gallery Inn

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$150 Along a winding street on Old San Juan’s cobblestoned lanes, you’ll find local artist Jan D’Esopo’s Gallery Inn, a lush retreat within six connected historic town houses. Inside is a labyrinth of staircases, open-air patios, hidden nooks, and no fewer than 19 gardens—some with night-blooming cerius, others with jasmine and orchids. The 22 rooms have draping floral tapestries, carved wooden headboards, and framed watercolors depicting scenes of the city by D’Esopo herself, who can often be found chatting with guests in her poolside studio.

T+L Tip: Try the traditional Puerto Rican fried red snapper with peas and rice at La Fonda el Jibarito (

dinner for two $30), two blocks away.

Best Affordable Caribbean Hotels

Puerto Rico: Gallery Inn

$150 Along a winding street on Old San Juan’s cobblestoned lanes, you’ll find local artist Jan D’Esopo’s Gallery Inn, a lush retreat within six connected historic town houses. Inside is a labyrinth of staircases, open-air patios, hidden nooks, and no fewer than 19 gardens—some with night-blooming cerius, others with jasmine and orchids. The 22 rooms have draping floral tapestries, carved wooden headboards, and framed watercolors depicting scenes of the city by D’Esopo herself, who can often be found chatting with guests in her poolside studio.

T+L Tip: Try the traditional Puerto Rican fried red snapper with peas and rice at La Fonda el Jibarito (

dinner for two $30), two blocks away.

Courtesy of Gallery Inn

Best Affordable Caribbean Hotels

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