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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.

Opened in May 2014 with a facade mildly reminiscent of a 19th-century European grand hotel, the Mandarin Oriental Taipei might seem incongruous in an Asian city—at least to those unacquainted with the Taiwanese penchant for blending international styles with more typically Asian motifs. The hotel’s Old World luxury extends throughout, from the marble-floored lobby (complete with white columns holding up high cathedral ceilings) to the rooms themselves, which are coolly stunning. Each room, from the standard Deluxe to the sprawling Presidential Suite, has separate tubs and walk-in showers inside a marble bathroom designed to make anyone feel like royalty. As for sleeping arrangements, “plush” is an overused word in hotel reviews, but it’s hard to find a better one to describe the feeling of sinking into a bed with 480-thread-count satin linen (which rises to 1,000 in certain suites) and a goose-down duvet. As a finishing touch, look up: Every room basks in the glow of its own chandelier. Though Marie Antoinette and the Empress Dowager Cixi lived on different continents, both would feel quite at home at the Mandarin Oriental.

If you’re visiting Tahiti with a large family or group of friends and hoping to surf the island’s most powerful wave, you’d be hard-pressed to find a better, more affordable place to stay than Green Room Villa. The 1,500-square-foot, four-bedroom property—the only vacation rental in the sleepy surfing village of Teahupo’o—practically opens up to the water and offers a unique place to rest your head. The main house is shaped like an octagon, with a huge mangosteen tree growing out of the open center, plus a large covered deck, teak flooring, and brightly painted walls that show off the owner’s creativity. The property even works well for a small destination wedding, as there’s a “honeymoon bungalow” near the fruit tree garden. Built on stilts, it sits over a purple-hued, lily-filled pond. It’s also the only room with air conditioning, although breezes keep the main house relatively cool. On a very local part of the island, Green Room Villa is extremely private, providing a relaxed place for your group getaway. Note: the owners require a credit card damage deposit and a three-night minimum stay.

Dar al Masyaf is a tranquil boutique hotel at the end of a white-sand beach, away from the package-tour and convention crowds. It’s located within the sprawling Madinat Jumeirah complex of seaside resorts and a shopping souk modeled after a traditional Arabian walled city. It’s all set next to the Persian Gulf coastline within a Venetian-style network of man-made canals. Rooms, served by butlers, are accessible by footpath and electric dhow and occupy 29 two-story courtyard houses with the same traditional wind tower architecture and calm vibe of the resort’s shared Talise Spa. Closer to the resort water park are the seven freestanding Malakiya villas, with huge marble bathrooms and fully equipped kitchens for family life. Getting in and out of the resort grounds, whose more than 50 bars and restaurants are a Dubai nightlife beacon, can mean negotiating a madhouse traffic jam of taxis and high-end sports cars. But thankfully, noise does not penetrate the rooms. The palm-backed beach is large enough for guests to find private space, and evening terrace views of wind tower lights reflecting in the canals can be enchanting.

Formerly Blue Sydney.

Carefully constructed around support beams and pipes from a 100-year-old wheat and wool wharf, this hotel offers a beautiful mix of old and new that juts out into the Woolloomooloo harbor. The Heritage Level is where you’ll find original wooden pier pilings, metal wheels, and conveyor belts that date to 1910, but classic touches such as early-20th-century photographs of Sydney are scattered throughout the property. Goose down bedding, plush furnishings, walk-in showers, and in-room iPads make modern travelers feel right at home, and the bar that runs the length of the central atrium—hanging Swarovski crystals shine pink and purple in the evening candlelight—often hosts fashion shows and cocktail events. Most rooms have sliding glass doors that take advantage of the hotel’s over-water location between the Royal Botanic Gardens and Rushcutters Bay; they open to either the city skyline or the Potts Point naval base. Maritime history buffs should book the latter and check out the site on the wharf from which sailors boarded ships for Gallipoli.

If there’s a hub of the hubbub in Kennebunkport, it’s Dock Square, a colorful jumble of onetime fishing shacks that now house galleries, stores, and restaurants. Prowl through the shops to find unusual clothing, distinctive souvenirs, fine art, crafts, taffy and fudge, pottery, canvas bags, specialty foods, presents for pets, and, of course, the usual trinkets and T-shirts. Most of these spots are built on wharves over the tidal Kennebunk River, and it’s worth climbing to second-floor ones, such as Good Earth, for the water—or mudflat—views. The bridge connecting Dock Square to Kennebunk’s Lower Village offers another good vantage point, and the Clam Shack is one of the area’s best places to indulge in fried clams or a lobster roll.

Some visitors to Santa Fe are surprised to find this Gothic revival structure in the middle of all of the adobe buildings in the historic district, like a piece of medieval Paris transplanted to the Wild West. The French connection is real—the 19th-century Loretto Chapel was designed by a French architect who modeled it after La Sainte Chapelle in Paris. According to legend, though, the plans failed to include access from the chapel floor to the choir loft. So, the nuns who ran the girls’ school for which this stone structure was built began praying, and after nine days, a mysterious carpenter arrived. Neither nails nor glue nor any visible external support were used in this doubly-twisting staircase, and no one ever found out the name of the carpenter, who left without seeking payment. It must’ve been St. Joseph himself...so goes the legend of “the miraculous staircase.” The physics of the structure can be explained by architects today, but that doesn’t stop about a quarter-million visitors every year from marveling at the elegant spruce spiral. Open to the public as a privately run museum, the Loretto Chapel hasn’t been a church for decades. It can, however, be rented: a spectacular setting for a private wedding.

O. Fournier is a modern architectural marvel located 80 miles (90 minutes) from downtown Mendoza in the district of San Carlos. It is one of Valle de Uco’s farthest wineries to visit, but it’s worth the drive to enjoy O. Fournier scenic views, distinctive design, and award-winning restaurant. José Manuel Ortega, a Spanish banker, bought the land in 2000 and contracted local architects to begin building O. Fournier in 2002. No expense was spared and no detail was overlooked to achieve Ortega’s vision. His talented wife, Nadia Harón, who delved into her passion for cooking when the pair moved to Mendoza, has become one of the country’s most notable chefs. Her restaurant, Urban at O. Fournier, blends Argentine and Mediterranean-Spanish flavors and traditions using fresh ingredients grown on the property’s 650-acre farm. If you find yourself falling in love with O. Fournier’s wine and landscape, you may just be tempted to purchase a small plot of land from Ortega to harvest your own wine and create your own signature blends. Reservations to visit the winery and restaurant must be made in advance.

For many Charlestonians and tourists, every Saturday is spent in Marion Square at the farmers’ market. Students nursing hangovers wait in line for a crepe at Charleston Crepe Company while farmers from John’s and Edisto islands sell their fresh vegetables. Artists sell their work while children play on inflatable slides and a guitar player keeps the crowd entertained. Between the French, Greek, Cajun, Spanish, Italian, Southern, German, and Indian foods on offer, you really can’t go wrong. Grab an assortment of foods to try and find a nice spot in the shade to eat and people watch.

If it’s not wintertime or you can’t get tickets to see the Maple Leafs play, then the next best way to experience Canada‘s game is by visiting the Hockey Hall of Fame. Situated in downtown Toronto, the museum is located on the lower floor of the Brookfield Place shopping center. It’s a short walk from the CN Tower and other attractions. (If you’re driving, you’ll need to find either metered parking or a parking garage, as there is no designated parking lot for the museum itself.) The Hall of Fame itself contains displays about historic moments in the game’s history, iconic jerseys and memorabilia from players, interactive games for children, and a room where the entire family can get up close with the Stanley Cup trophy.

Brooklyn has become a dining destination in recent years, with dozens of restaurants preparing local, organic, and sustainable American dishes—and others serving everything from Korean bibimbap and Scandinavian specialties to Ethiopian stews and Mexican tacos. The borough has an overwhelming abundance to choose from, but Smorgasburg makes it easy to graze and sample a variety of Brooklyn’s dishes. From the beginning of April to the end of October, food trucks and stalls representing around 100 restaurants and other establishments set up at East River State Park, in the Williamsburg neighborhood, every Saturday; on Sundays, you’ll find them farther south, in Prospect Park. The largest weekly open-air food market in the country, it’s popular and draws thousands of visitors, but don’t be deterred by the crowds: Much of the fun is the people-watching and the general festival-like atmosphere. Even if you aren’t visiting New York in the summer, it’s worth checking out the Smorgasburg website as they sometimes have smaller off-season pop-ups, including the Winter Flea & Holiday Market.

A stroll of St. Kitt’s capital, whether started at Port Zante Marina or the centrally located Independence Square, is an entertaining way to learn more about the island’s past. While the French named Basseterre (it means “low land”), the British are responsible for the town’s most recognizable landmark—the green, cast-iron Berkeley Memorial Clock in the center of the Circus, where several streets intersect. Make sure to visit the area, as well as Independence Square, St. George’s Anglican Church, and the Old Treasury Building, which now serves as the National Museum of St. Kitts. Along your walk, you’ll also find duty-free shops and local boutiques, plus a lively produce market by the waterfront if you come on the weekend.

At 4,235 acres, Mission Bay Park is the largest man-made aquatic park in the U.S. Here, water-sports enthusiasts can enjoy everything from kayaking, windsurfing, and wakeboarding to snorkeling, scuba diving, and fishing, while landlubbers can take advantage of several trails and grassy areas. For equipment rentals, head to the Mission Bay Aquatic Center, located right on the bay.

Located in a former shoe factory, City Museum devotes 600,000 square feet and four levels to play for all ages. The museum was the brainchild of artist and entrepreneur Bob Cassilly—along with a crew of 20 artisans known as the Cassilly Crew—who constructed the space from objects found around the city, from construction cranes and fire trucks to church pipe organs, old airplanes, and plenty of reclaimed building materials. The result is a wonderfully weird and wacky museum that’s constantly evolving, depending on what’s been donated and collected recently. There’s a sky-high jungle gym, a rooftop Ferris wheel, an aquarium, and multi-story slides that once served as chutes for shoes. The museum has a “no map” policy to encourage exploration, but does advise visitors to bring their own flashlight—you never know what you’ll find in those dark caves.

Puerto Princesa Underground River is set in a protected area of the St. Paul Mountain Range in Palawan. It’s a five-mile stretch of the Cabayugan River that runs through a huge limestone cave and directly into the West Philippine Sea near Sabang village (the bottom half of the river is tidal). Announced as one of the New7Wonders of Nature in 2012, it’s hard to fully envision unless you experience it for yourself. Reservations are required for the tours, which enter the underground river on a small boat. The boatman manually paddles you in as the light fades, the water becomes pitch-black, and you almost lose sight of the person beside you. The boatman will then start flashing his tiny light on the stalactites, stalagmites, and other rock formations you pass. The tour takes about 45 minutes and covers only a mile or so of the river (the inner portion is closed to the public).