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A breezy little beach hotel filled with rough wood, natural linen, and flea market finds, the Rose seems, to the uninitiated, like a pure product of quirky Venice’s hipsterfication. In fact, the historic, wood-and-stucco building was built by the beach town’s founder, Abbot Kinney, in the early days of the 20th century; rumor says it was his private brothel, frequented by such friends as Charlie Chaplin. By the 1970s, at the height of Venice’s drug culture, the building had become a flophouse of sorts, and neighbor Dennis Hopper was known to drop by. Before two British photographers discovered it, the house had turned into a mural-covered crash-pad for surfers, yogis, and beach bums of all kinds.

Looking at the low-key Rose now—the town’s first true boutique hotel, barely half a block from the beach—one would hardly know that the entire history of Venice had passed through it. The rooms are spare but stylish, with large windows, art photography, and vintage furniture. Some rooms are large enough to live in, whereas others share a hallway bathroom. Amenities are minimal—Stumptown coffee, bicycle rentals—but a relaxed beach house that attracts artists and creatives looking to delve into Venice’s eclectic, vibrant culture doesn’t need to try too hard to be cool.

Near the northern end of Andros Island, about 15 minutes by air from Nassau, remote Kamalame Cay is worth the effort it takes to get there. The 96-acre private island features 34 rustic-chic rooms and suites, all within steps of a white-sand beach, as well as a central Great House where guests come together to sip wine before dinner and share stories afterward (of course, many opt for a secluded, candlelit meal set up somewhere along the three miles of shoreline). A range of seaside activities keep everyone from the kids to newlyweds to the occasional celebrity happy. There’s a freshwater swimming pool, an over-water spa, world-class fishing off the coast, and entertainment by local “rake-and-scrape” bands. And for those who live in fear of being unplugged, relax. Kamalame Cay offers hotspots around the island for full cell service (if you want it) and Wi-Fi in the reception area.

The first luxury lodge to come to Chile’s second biggest island, Tierra Chiloé opened in 2012 and became a member of the Tierra hotel group in 2014. Designed by Chilean architect Patricio Browne, the hotel looks like a boat on stilts and was inspired by the homes of local fishermen, which take the same form and are known as palafitos. The exterior is made from picturesque larch wood shingles—a building technique that’s very typical on Chiloé and is seen on the famous UNESCO World Heritage churches that dot the islands.

Inside, guests find more wood. The hotel’s wood walls and ceilings are made from indigenous species . The decorations are locally inspired with plenty of handicrafts such as wicker baskets, handwoven rugs, and wooden carvings. The focal point is the meadow and Reloncaví Sound below, where the hotel’s boat is harbored. Large windows line the building on both floors and provide excellent views. Guests can relax in a small spa, a winetasting room, or a book-filled upstairs studio upstairs. The living room with fireplace makes a perfect spot for an end-of-day pisco sour.

As the camp’s name indicates, the main reason to stay here is to catch the Great Migration, the annual movement of more than one million wildebeest and hundreds of thousands of zebra and gazelle making an 1,800-mile circuit through the Ngorongoro Conservation Area, Serengeti National Park, and into the Maasai Mara in Kenya. At the camp, large, tented chalets on stilts have wraparound decks with a 360-degree view of the landscape and its denizens. The lodgings blend into the surroundings on the bank of one of the great migration obstacles: the Grumeti River, with its many crocodiles, hippos, and boulders. Herds pass through the vicinity from August through November, and the Elewana’s northern Serengeti location miles from the main concentration of game lodges gives it a sense of privacy rarely achieved in the far more visited western and southern park corridors. One further advantage: The camp is within driving distance of the other great wildebeest crossing point, the Mara River, on the border region between the Serengeti and Kenya’s Maasai Mara National Park. The atmosphere at the lodge is cheerful and relaxed, and the huge tented suites, which are divided by canvas walls into bedroom and bathing areas, have comfortable queen or twin beds, wood floors, colonial-style leather chairs, African textile accents, and, unlike most mobile migration safaris, hot water and electricity 24/7.

If you’re looking to escape the tourist hubbub in Dubrovnik’s historic core, follow the locals to Lokrum. Just a 15-minute ferry ride from the Old Town, the island offers magnificent nature walks through botanical gardens and olive groves. Paths climb up to sites like the oldest Benedictine monastery in the region and Napoleon’s Fort Royal at the very top, passing native peacocks along the way. Come for a relaxing stroll, a picnic in the shade, or a refreshing dip in the sparkling Adriatic.

Along the glittery street of Collins Avenue in South Beach is the Raleigh Hotel, a smart and stylish blend between sparkling lights of Miami and the rich history that old Florida is known for. Immerse yourself in the calming and relaxing vibe of the hotel from the moment you enter the the lobby. Sip a martini at the bar that has been serving shaken cocktails for nearly 50 years.

Take a seat on one of the plush couches and get into the luxurious and sensual atmosphere that keeps South Beach at the top of its game. If you are hungry, make your way to the outdoor restaurant, Restaurant Michael Schwartz located along the twinkly lit bar on the patio. Chef Michael Schwartz helms the kitchen, using farm fresh ingredients and local seafood.

Once you are finished sampling the variety of specialty cocktails with fresh smoked herbs and prime liquors along with crispy crab cakes and shrimp toast, head to the expansive pool patio, which seems to go on forever. It is commonly known as the most famous pool in Miami.

The Raleigh is most well known for hosting Miami Swim Week, where the top names in fashion will sit along the twinkling trees and poolside cabanas to view the next seasons swimsuit trends.

A serene respite from the towering urban sprawl nearby, this traditional Tang Dynasty–style landscaped garden is based on the design of the famous Jiangshouju Garden in Shanxi Province. Winding paths lead visitors past pines, cypress, and fragrant flowering trees. Set on Diamond Hill in Kowloon with the vast northern mountain range as the backdrop, the lovely park has been designed with artificial hillocks, ornamental rocks, waterfalls, and koi ponds to encourage quiet walks and reflection. Think of it as an outdoor museum for the soul and a place representing Chinese cultural ideals. A striking gilded pagoda and a pair of arched red wooden bridges are the focal points of a lotus pond and a favorite photo subject. To linger longer, enjoy a meal at the vegetarian café on-site.

In the spirit of going big or going home, Hakkasan Las Vegas is a nightclub that basically outdoes all other when it comes to size and entertainment. To begin with, there is a two-story restaurant, which has a contemporary design and offers the perfect place to warm up for an evening in the nightclub. The club, which encompasses levels three, four and five, has a variety of rooms, each with its own feel and vibe. Level three consists of the Ling Ling Room and Club, which are chic and, in the case of the lounge area, dark and sleek as well. The main nightclub is located on the fourth floor; this is where party goers can watch DJs like Calvin Harris, R3hab and Tiesto perform. The fifth floor houses the Pavilion, which has an outside-type of energy. Come for dinner and stay all night long, rotating between the many nightlife experiences to say you’ve done a little bit of everything in Las Vegas.

While the Monterey Plaza Hotel is centrally located on the end of Monterey’s main tourist drag, Cannery Road, each of its 290 rooms are a comfortable, quiet retreat from the world.

We picked up some gyros to-go during our stroll through the historic Plaka neighborhood below the Acropolis. Thespidos street was particularly memorable for the cafe we stopped at and discovering Brettos bar, which we decided to come back to enjoy as the end a lovely evening.

Big baggy aloha shirts—that could double as canoe sails—goodbye. Instead head to this Chinatown boutique, featuring the sharp, tapered designs of the eponymous Roberta Oaks. She draws on her hippie, farmhouse childhood and mid-century modern Hawai‘ian flair to create prints, which she then combines with a more fitted and form-flattering modern silhouette. These fabrics also take a star turn on graceful day dresses and even doggie bandanas. Open since 2009, this alluring boutique goes beyond attire, selling jewelry, candles, surf photography, and scents like Sándalo (a moody meditation on the islands’ vulcanism with ash, patchouli, and Royal Hawai‘ian sandalwood).

One can’t help noticing Brazil’s stark social contrasts, especially visible in Rio thanks to rich neighborhoods that often sit cheek by jowl next to some of its poorest, the city’s famous favelas. High up in the favela called Tavares Bastos, visitors can take in an evening that includes some of the city’s best jazz, yet in a setting like few others: a boîte called The Maze. The owner, a British artist and longtime Rio resident, first decided to mount a First Fridays show in 2005, and those monthly events have become a citywide musical tradition. Those who journey up—aboard a minibus or in a taxi—will get breathtaking vistas to go with the great entertainment.

Tucked away on an eight-acre estate at the top of St. Helena’s main street, Harvest Inn could easily be mistaken for a private country manse somewhere in England, or even northern France. Its lush gardens are traversed by winding pathways, and its brick-accented, Tudor-inspired architecture suggests somewhere far more Old World than upstart Napa. Even its sinuous pools and cozy rooms (many with fireplaces and private outdoor hot tubs, mind you) are reminiscent of a style somewhat less rustic-chic than tends to be in vogue here in wine country. Indeed, by Napa Valley standards, the intimate inn is part of the old guard, its original 25 rooms dating back to 1975, just after the famed Judgment of Paris tasting brought the region’s New World wines into the international spotlight.

But the Harvest Inn is no less luxurious than the new resorts popping up all over Napa Valley. It has one of the most desirable locations in one of the most desirable parts of the world, surrounded by celebrated vineyards and presiding over arguably the most picturesque town in wine country. It also features a popular restaurant, Harvest Table, which serves dishes full of ingredients from the hotel’s on-site vegetable and herb garden.

Some may scoff at the absence of beachfront acreage, but what all-inclusive Capella Marigot Bay lacks in sand it makes up for in amenities, including a cabana-lined pool area with swim-up bar and a ferry to nearby LaBas Beach. Backed by a see-and-be-seen marina that offers some of the island’s best people-watching, the hotel features 124 luxurious rooms and suites that are studies in restraint, with dark-wood accents and four-poster beds trimmed in mosquito netting. Guests are surprised with complimentary snacks each day, from house-made plantain chips to local Piton beer, but nourishment is also in abundance at the resort’s four restaurants—think fresh-caught snapper, jerk-spiced ribs, and lionfish ceviche—and during three happy hours. Meanwhile, the celestial-inspired Auriga spa offers locally focused treatments to those less interested in the fitness center and weekly activities such as body-scrub-making workshops and zip-line tours.

With its 26 suites, private beach, and two waterfront bars, Calabash Cove offers a boutique hotel alternative to the typical all-inclusive experience. Set a stone’s throw from the turquoise waves of Bonaire Bay, the sprawling, Balinese-inspired Water’s Edge cottages are the ones to book thanks to private plunge pools, outdoor rain showers, and patio hammocks positioned to highlight superb sunsets. The resort’s remote location ensures tranquility, as does the spa, which offers in-room treatments using ingredients sourced from St. Lucia’s floral and culinary bounty. That abundance is also on display in the Windsong restaurant, where local dishes get an elegant twist (octopus tempura, smoked coconut crème brûlée) in a terrace dining room with the ultimate ocean backdrop. Follow your meal with a brief walk down Calabash Cove’s small boardwalk and stop to spot shooting stars in the dark skies above.