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Occupying three whitewashed colonial buildings sheltered from the bustling streets of Old Town Cartagena, Casa San Agustín sits on the site of a former aqueduct and channels its heritage with a swimming pool that tunnels through its stately remnants. Inside, common spaces feature a mix of Colombian art and artifacts with contemporary wicker furnishings and marble floors. The 20 rooms and 10 suites are cozy and a bit more polished than those found at other historic properties nearby: Units feature 200-year-old wood-beamed ceilings and iron canopy beds topped with Frette linens; some have patios with hot tubs or brick terraces with views of surrounding buildings. But there’s plenty of space to unwind throughout the property, namely a library with original frescoes and a lounge with a long wooden bar and ceiling-high wine cabinet. It’s a good idea to make reservations in advance for dinner at Alma, considered among the city’s best restaurants, where the upscale international cuisine includes fresh ceviche and dry-aged beef cured on-site.

Casa Vicente is an institution in this desert city—Tucson’s outpost for tapas a la española. Just south of the downtown core, a couple of blocks from the neo-Baroque façade of the Cathedral of San Agustín, this restaurant also features live music on weeknights: classical guitar, flamenco, and even tango lessons. This particular evening, we tried chipirones rellenos, a trio of baby calamari skewered and stuffed with green tomatoes and spices. In a town more known for its tacos and burros (a.k.a. ‘burritos’ elsewhere), it’s appropriate, if somewhat uncommon, to find Iberian fare. Tucson was founded in 1775 as an outpost of the Spanish empire, decades before it became Mexican, and then in the mid-19th century, it finally became part of a U.S. territory. (And, by the way, the sangría here rocks.)

When you eat at Casa Tua you are more than a guest at a restaurant. They make an effort to make everyone feel like they are visiting the home of a friend. Split into two levels, the top level is for members only. The bottom level is open to the public for dining and even though you may not be a member you are still treated like family. The kitchen is an open kitchen with viewing windows. The menu is designed as a four course Italian meal. Start the night with their famous Bellini and antipasta.. Their Burrata is to die for and melts in your mouth. Move on to the first course, or primi platti, with a paired wine that their sommelier can help you choose from their excellent wine list. After that, although you feel like you have already had a full meal, there is the main course of meats, fish and poultry. Hopefully you saved room for dessert because you won’t want to miss their Tiramisu.

What is more romantic than an intricate and well-used Spanish fan? Fans are a highly personal item, and like perfume, one should only use the best they can find (or so my mother always said). For the royal minded there is only one choice, Casa de Diego. Founded in 1858, this a business steeped in international approval, and the generations have been privileged to create masterpiece shawls, umbrellas, and of course fans for royal families all over the world. Proudly facing the Puerta del Sol is the window display of fans, giving only a glimmer into the magic on the other side of the doors. Right outside is the hustle and bustle of city center, but inside the shop you are transported to a haven of beauty. Take home a piece of Spanish tradition with you, and smile every time you fan yourself, remembering Madrid.

The Catalan capital has plenty of places to cozy up with your loved one and enjoy your drink of choice, be it a meaty Tarragona red or a café carajillo—the Spanish spin on Irish coffee. Lean your elbows on the marble tables of Casa Almirall, located in Barcelona’s gritty Raval neighborhood and founded in 1860, while nibbling olives and sipping the house vermouth on the rocks. Alternatively, share a bottle of cava at El Bosc de les Fades, a fairytale forest-themed café inside Barcelona’s Wax Museum off La Rambla. With its soft lighting and bohemian ambiance, Andú (c/Correu Vell, 3) is the perfect place to share cava and light tapas in a homely and intimate setting.

The atmosphere at this high-end bookstore in Colonia Roma brilliantly walks the line between book-as-information and book-as-object. The visual impact is absolute: Impeccable volumes are showcased on matching shelves that rise like cliff faces on either side of a long table that also supports eye-catching tomes. The inventory is focused on art, architecture, design, fashion, and photography, with forays into food and film. Titles clever as well as weighty spur readers to take on abstruse theory, or paradigm-shifting essays, made more amenable in physical books (remember those?) that are downright gorgeous. Every title on offer was gathered from the booksellers’ associations with indie presses or was collected as they made their way along the global art and design circuits.

Why we love it: A 19th-century palazzo-turned-boutique-hotel that’s full of sophisticated details

The Highlights:
- Historic details like restored tiles, antique furniture, and traditional Maltese wooden balconies
- Guestrooms with deep-soaking tubs or Jacuzzis
- A central location just off Valletta’s main drag

The Review:
Formerly home to the Ellul family, this Victorian-period palazzo is now an exceedingly charming boutique stay that’s a member of the Small Luxury Hotels of the World. Fourth-generation brothers Matthew and Andrew Ellul converted the property, which sits on a quiet but easily accessible side street, into nine luxurious guestrooms, each uniquely decorated with restored Maltese tiles, wrought iron accents, richly hued rugs, and antiques sourced from around the world. Rooms also feature original works by local artist Ritty Tacsum as well as either a private terrace or traditional Maltese wooden balcony. One suite even has a piano, while several others boast free-standing bathtubs or Jacuzzis. In keeping with the Casa Ellul’s family-owned ethos, service here is friendly and personalized, making guests feel as if they’re staying in a friend’s home.

Why we love it: A design-forward oasis for creative nomads

The Highlights:
- The bright and airy inner courtyard with a massive chaca tree
- Regular programming like live music and wellness workshops
- No single-use plastics in sight

The Review:
From Tulum tastemaker Derek Klein (of Gitano fame) comes this minimalist tropical hotel on the edge of the ever-expanding city. Imagined as a hub for creative types, Casa Pueblo hosts wellness workshops, live music, readings, and other community events, but also boasts amenities like a saltwater pool, rooftop bar, and in-house restaurant situated in an airy central courtyard. Yucatan textiles and handmade pottery can be found in various nooks and seating areas.

The hotel’s 16 spare rooms face into the courtyard and feature clean white-plaster walls, hand-sculpted bedside sconces, carved wooden furniture, and slatted wooden shutters covering floor-to-ceiling windows. Luuna memory foam mattresses wear Parachute linens and bathrooms showcase custom-made concrete sinks and open rain showers. Purified water in glass carafes and full-size organic Loredana bath products mean no single-use plastics, helping the hotel remain 99 percent plastic-free.

Why we love it: A city slicker–approved beach retreat with a vibrant art collection

The Highlights:
- The secret indoor pool up a staircase from the main pool area
- Fresh-baked breads by pastry chef Simone Colla served daily in the Filosofía restaurant
- An entryway featuring a rare sculpture by KAWS and vintage armchairs hung like swings from the ceiling

The Review:
The people watching is just as entertaining as the artwork at Casa Malca, a mansion once maintained by Colombian drug lord Pablo Escobar but now owned by New York gallerist and art collector Leo Malca. Set on a Caribbean-facing swath of sand next to the Sian Ka’an Biosphere Reserve—and just a short bike ride from Tulum’s beachfront boutiques and restaurants—the hotel features 71 rooms, complete with polished concrete floors, floor-to-ceiling windows overlooking the ocean, and bold artwork from Malca’s personal collection. A black-and-white print inspired by Keith Haring covers the lobby bar, while antique baby dolls adorn the walls in one of the hotel’s three restaurants. The pool and beach areas are more sedate, with cerulean daybeds and colorful hammocks studded like jewels among the leafy palms.

Hundreds of years ago, at the height of Florence’s Renaissance heyday, visitors to this cultural capital wouldn’t have stayed in the kinds of luxury hotels that now line its picturesque streets. Rather, the well-heeled would have come at the behest of friends, lodging in private homes whose unassuming facades in the best neighborhoods belied their sumptuous interiors and private gardens, outfitted with art and artifacts collected from around the world.

A guesthouse to its core, Casa Howard continues this Florentine tradition; there is neither lobby nor restaurant, and the owner Massimiliano Leonardi di Casalino lives in his own apartment here while in town (note, it can be rented when he’s away). Jennifer Howard Forneris, one of the design-conscious proprietors who has since passed away, was the daughter of renowned textile designer Luciano Forneris. She gave each room its own look, with finds from her and Leonardi di Casalino’s world travels. A media room is the sole common area, and a hammam steam room and an on-site concierge service are the only nods toward traditional hotel services. Insider recommendations are personalized according to guests’ preferences, and the honor bar feels more like a friend’s (well-stocked) fridge.

The mysterious rooftop of Casa Mila both charms and haunts visitors. The glorious October sky above frames the organic forms, each sculpted face watching as I creep up and down the rolling ramps. Children can’t resist playing here, and fortunately there are now fences all around. In my mind, I erase all of those pesky safety features to envision the smooth sculptures growing towards the sky from a scrolling sandy field. Once a site for a scene from Star Wars, the rooftop is now a destination for lovers of Barcelona and Antoni Guadi’s “Modernisma” style. When you visit, you’ll learn the secret behind those long vertical faces rising up above the mystical rooftop.

Though from Guadalajara (he never let friends forget), Pritzker Prize–winning architect Luis Barragán lived much of his life in Mexico City, where he designed and constructed this, his last residence, completed in 1948. A UNESCO World Heritage site, the home is open to be toured by small groups—by appointment only; English-language guides are available upon request—who want a chance to tap into Barragán’s brand of minimalism, which involved bold monochromism and a masterful use of light; striking horizontality and framing applied to windows, gardens, and views; a highly sui generis Catholic spirituality; and, not least of all, the architect’s bizarre need for control, in everything from what staircases guests might use to what records got played in different rooms.

Small and intimate, Hotel Casa Oaxaca feels quintessentially Oaxacan: It’s colonial in style, with whitewashed walls contrasting with vivid pops of carnelian red and fuchsia. It’s surrounded by local vegetation. And it’s filled with Oaxacan handicrafts and art. Common areas invite visitors to settle in and relax, like the on-site library, pool, and terrace with beautifully-made cotton hammocks. The hotel’s seven rooms are arranged around the central patio. Visitors consistently say the service is exceptional, with attention to detail and a “go the extra mile” attitude mentioned frequently as one of the main reasons to return. Another is the hotel’s central location, as it offers an easy walk to many of Oaxaca’s top sights.

Key West doesn’t have many swimmable beaches, but this elegant 1920 oceanfront resort sits on the largest private one in town—an 1,100-square-foot strand punctuated with tall palms. While the shoreline itself is on a rocky shelf, a long dock extends out to the shallows for laps and snorkeling. Just off the beach, two large pools are set into green lawns and lush landscaping in front of the Spanish-style main building, which is on the National Register of Historic Places. The hotel’s wooden coffered ceilings, arched entryways, red-tile roofs, and other key architectural details recall the hotel’s glamorous heyday, while the clean, refreshed rooms are entirely modern, with sleek wood-framed beds, white linens and curtains, and ocean views. Children under 16 stay for free and babysitting is available for adults who want to take a break at the Spa al Mare, which has an open-air cabana right on the sand for al fresco massages and treatments.

Steps away from Mérida’s prestigious mansion- and monument-lined Paseo de Montejo, this residence turned boutique hotel is a stylish retreat full of Instagrammable moments. Colonial-era details like wooden antiques, wrought-iron chandeliers, and exposed ceiling beams are sprinkled throughout the seven guest rooms, but modern comforts keep things current—think bathrooms with organic toiletries and rain showers illuminated by skylights. There’s plenty of tile flooring and colorful art on the walls, but the most scenic spots are the breezy colonnaded patios that overlook the hotel’s lush outdoor spaces. Head to the tranquil pool area to while away the time with a good read or an expertly crafted cocktail in one of the hammocks that swing beside the water. The next best seat in the house? You’ll find it on the breakfast patio, overlooking the palm-dotted garden. A seat at the granite-topped bar isn’t too shabby either, with personable bartenders serving up a wide variety of top-quality tequilas.