La Purificadora, Puebla
Price: Doubles, $120–$210
A nineteenth-century water treatment plant in the heart of this charming city's Baroque district has been transformed into La Purificadora, a modern marvel from acclaimed Mexican architect Ricardo Legorreta. The hotel integrates the original stone facade seamlessly into its three-story open-air lobby. Legorreta makes liberal use of black and white tones, seen first in the onyx tile floors and whitewashed walls. The lobby is accented with boxy purple furniture—a nod to the colorful frocks of Roman Catholic bishops—surrounding glass tables and slab-stone gas fire pits. The hotel's 26 rooms are spacious, and most overlook gardens and the sixteenth-century Iglesia de San Francisco—views made doubly delightful from glass-walled balconies that seemingly float on air. A small aboveground glass pool on the roof is the place for an aquarium-inspired dip­—as long as you don't mind the stylish set taking in your stroke from the sundeck. Get that swim in early because after dark the deck—which has stunning views of Puebla—turns into the city's hippest bar.
Book: It's all about the views from the corner suite balcony (52-222-309-1920; lapurificadora.com).
Best for: Modern-architecture junkies.
Rental car: Required only for adventures outside Puebla.

PUERTO RICO

El Convento, San Juan
Price: Doubles, $270–$390
A grand vestige of Old San Juan's Spanish colonial past, El Convento is the loveliest hotel in the city: Marble bathrooms, wrought iron canopy beds, tapestries, and carved desks in the 58 rooms set a comfortable, opulent tone. Housed in a former convent, the hotel is large and frames a charming central courtyard that's a popular wedding spot. It's a prime location in the seven-square-block neighborhood of Old San Juan, which is filled with forts, museums, and more than a few bars—notably Rumba, a salsa club with a Dirty Dancing vibe (152 Calle San Sebastián; 787-365-1418). Daily wine receptions are held on a terrace overlooking the old cathedral, which can also be seen from the small rooftop pool and hot tub.
Book: Higher rooms are nicer and recently renovated (787-723-9020; elconvento.com).
Best for: History buffs who want a private retreat. Rental car: Required only if you're traveling outside of San Juan.

Gallery Inn, San Juan
Price: Doubles, $175–$270
The rambling 22-room Gallery Inn occupies six connected houses in a historic area of Old San Juan where artiness abounds: World-class pianists appear several times a month to play concerts on the nine-foot Steinway in the hotel's elegant music room, and owner Jan D'Esposo spends her free time creating paintings and sculptures for her adjoining gallery. Assiduously faithful to the city's history, D'Esposo built a garden pool framed by walls that are hundreds of years old. The food is great, whether it's the morning's homemade guava jam or the starchy cassava bread drizzled with olive oil and garlic served later in the day. And while the Atlantic breeze is responsible for small mold patches on the bathroom ceilings of at least one ocean-facing room, it also carries the musical chatter of cockatoos and macaws into the inn's public areas.
Book: A room with a balcony (787-722-1808; thegalleryinn.com).
Best for: Extroverts who'll relish the daily wine-and-cheese hours and gregarious hosts.
Rental car: Required only if you're traveling outside San Juan.