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When I first moved to the island, I joined a friend in the Old City for a tour and lesson on the history of Puerto Rico. When passing by this little section of town near Pigeon Park, my friend and native-turned-tour-guide said that this was the smallest house in Old San Juan. Wow, okay, so this little yellow portion is technically a house? I’ve visited this site several more times since then and have never actually seen anyone enter or leave this door. Whether it’s true or not, it makes for a cool story and great photo.

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.

A new Swedish pop music group perhaps? Not quite. On my road trip through Southern Sweden, an architect friend of mine insisted we stop in Malmö to see Santiago Calatrava’s building, the Turning Torso, which was modeled after his own human form sculpture, the Twisting Torso. My friend described the town as “plastic fantastic” because of the vast variation in new architecture styles here, remarking that the Turning Torso is such a notable find within its more sober surroundings. It is, after all, the third tallest residential building in all of Europe. Artsy and industrial, for me, Malmö is reminiscent of something like Dumbo, Brooklyn. Passing through on our road trip, I daydreamed of moving into a loft space in this dynamic city where a majority of the population is under 35.

Though less decadent than some of the medina’s more storied hotels, Riad Ahlam offers charm in spades at budget-friendly rates. With its trickling fountain and potted citrus trees, an elegant central courtyard is the setting for highly Instagrammable daily breakfasts brimming with homemade pastries and breads, fresh fruit and juices, sweet jams, and aromatic coffee; lunch and dinner highlight typical Fassi fare such as spiced tagines and vegetable couscous. Guests seeking pampering can indulge in a massage on-site, then retreat to one of eight rooms featuring colorful local textiles, traditional Moroccan lamps and lanterns, and brightly hued bathrooms with mosaic-tiled showers and shiny copper sinks. There’s also a scenic rooftop terrace, a prime perch for a cup of mint tea with a view.

Families traveling with children will love Ecoism, located at Costa Navarino’s Navarino Dunes. Here you’ll find 100 percent organic children’s clothing and eco-friendly toys crafted from natural materials. Their selection of high-quality wooden toys is especially interesting, with clocks, puzzles, and doll houses.

This super-exclusive private club opened recently in the chic Palermo Soho district. Members or friends of members can go to the garden bar for poolside drinks. It’s all the buzz in Buenos Aires. 54/(11) 4832-5276.

• Neighborhood: Sentosa Island
• Why we love it: A secluded off-mainland retreat with mahjong and feng shui lessons
• From $1,180

Refreshed in 2021 by Hong Kong designer André Fu, the 112-room Capella Singapore plays up its idyllic beachfront setting. The stylish, ultra-comfortable rooms have a palette of soothing sand, sage, and mineral gray and come with deep soaking tubs and window lounges that frame green jungle foliage.

Beyond the striking design, standout amenities include a three-tier infinity pool and an award-winning art collection (there are more than 900 pieces on-site). Also notable is the Capella’s Culturalist activity calendar, which offers lively mahjong lessons, farm-to-table cooking classes, and a sidecar tour with a feng shui master who explains how the ancient Chinese philosophy influenced the placement of Singapore’s iconic Marina Bay Sands and the mystical Merlion statue.

One of Austin’s top boutique hotels—and among the first in the trendy East Austin neighborhood—the Heywood Hotel feels more like an achingly cool designer friend’s house than a hotel, and in the best possible way. The husband-and-wife team renovated and expanded upon a 1920s Craftsman bungalow and outfitted each room with his handmade furniture, and art and textiles by local artisans. They also added the most comfortable beds they could find, Kevin Murphy’s Kakadu plum hair products, and Internet jukeboxes (a necessity in music-loving Austin). No, there isn’t a restaurant, or even a bar, but there’s a front porch and a courtyard patio where you could eat local snacks, sip beers, or try “Heywood blend” coffee. Complimentary bicycles are available, and a team of local experts on staff who have an endless supply of suggestions for drinking, dining, and exploring in the up-and-coming neighborhood—just like a friend would.

La Poza del Obispo (Bishop’s Pool) is a hidden treasure near the Arecibo Lighthouse in Puerto Rico. This beach is loved for its contrast. You will find a calm spot (though it can get rough in bad weather) where you may float, swim, or simply stand around talking to friends. This area is surrounded by limestone rocks. On the rocks and beyond them, as you near the open sea, large bursts of water spray into the air. The water is so clear that a fish and I once became friends. He kept swimming by my side and stopping when I stopped. The tiny silver and blue fish amused me for quite a few minutes. It’s a clean little area where you can sift through seashells and, if you snorkel, you can take a peek at coral on the rocks. Feel free to bring food and have a picnic, since there are a couple of tables and trashcans around.

Located on the north side of Playa del Carmen, the family-friendly Plaza Las Americas houses 12 movie theaters and well known Mexican department stores such as Liverpool and Sanborns. There are also clothing shops and boutiques, as well as a supermarket and large food court.

Coda is a locally owned shop in Houston Heights with a unique collection of rustic, industrial, and contemporary home decor and gifts. I especially love the candles and handcrafted bath and body products. Ask the friendly owner, Frank, for help picking something out if you need a second opinion.

Explore Catalonia’s largest lake in Banyoles. Walk or jog around the rim, snap shots of friendly waterfowl, or jump in for a swim. Visitors can also kayo, canoe,or fish. Afterwards, dry off and take a turn around the city’s charming old town.

With a menu based on fresh ingredients, a great staff, and a very family-friendly attitude (and even a hip edge), Preysinggarten is a place to unwind, and bring the kids! A beautiful interior, and even an outdoor play area (spielplatz) for children—it’s a very cool place in a hip neighborhood.

Matteo Donini, aka the Don, opened his hidden art gallery in 2008 as a celebration of street artists, many of whom are his friends. If you find yourself in the Isola neighborhood in the late afternoon, ring the bell and see what happens.

JK Place Firenze is a far cry from Florence’s obsession with all things Renaissance. Set amid the buzz of Piazza di Santa Maria Novella, this onetime private mansion is decked out in black, white, peach, gray, and chrome, with inflections of 1950s movie stars, 1970s pop art, and ornate 19th-century architecture. The reception feels like a library, and the breakfast room is a glassed-over former courtyard with a hefty antique wooden communal table. Free drinks, fresh fruit, and homemade treats (and bubbles at cocktail hour) can be found at all hours in the guests-only lounge area. Impress your well-heeled friends by inviting them to dine on the piazza terrace, presided over by the appropriately black-and-white Basilica di Santa Maria Novella, before moving downstairs to the clubby J.K. Pink Room. Slip upstairs to your individually designed room for a divine night’s sleep, then awake ready to take on one of the world’s most historic cities.