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. The owner, Jan D'Esopo, is a well-known sculptor whose works dot the meandering interior, which has enough comforts and homey character to avoid feeling like a museum. The oldest building, La Cueva Del Indio, dates to the mid-1700s, and its location above Old San Juan's north walls means the views out to sea are the same ones that captivated the conquistadors. Each of the 25 rooms is as unique as D'Esopo's artworks. Don't even think about watching TV: one, there are no TVs, and two, the views out over the old fortress walls to the ocean are better than anything on a screen.
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Old San Juan is one of the world's great cities to explore on foot. Established in 1521, it is bookended by the vast and forbidding fortresses El Morro and Fuerte San Cristóbal. Within this compact peninsula you can wander from one timeless street tableau to the next. Old stucco homes sport elaborate iron grillworks. The cobblestone streets are full of locals heading to the market, couples promenading at sunset, and visitors busily gawking. Restaurants, from simple cafés to celebrated culinary hot spots, dot the storefronts.
Need to Know
Rooms: 25 rooms and suites. From $95. Check-in: 3 p.m.; check-out: noon. Dining options: The hotel has an honor bar for guests, which is open throughout the day. From 4:30 p.m. to 10 p.m., a waiter is on duty to serve drinks and small plates of tapas. At least two times a week, the menu expands to include Puerto Rican specialties. Spa and gym details: The hotel has no spa or gym, but guests can head out for jogs or walks around Old San Juan's walls.
Who's it for: Adventurers who love art and comfort. Travelers looking for a hotel with personality. Our favorite rooms: Every room is distinctive, but San Sebastian makes you feel like a Spanish noble. It has richly appointed sitting and dining rooms, while the bedroom has 20-foot ceilings and tapestry-lined walls. Living history: Owner Jan D'Esopo dons period costume for her art and history tours of the inn, which start with a drink at the inn's wrought-iron gates and include stops for snacks along the way.