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It’s not that newer is necessarily better—Antonio Obrador, the hotelier and designer of famously luxurious retreats like Mallorca’s Cap Rocat, would hardly choose a neoclassical, turn-of-the-century palacio for his latest project, were that the case—but when a hotel gets the kind of buzz that the Urso Hotel & Spa got when it opened in the fall of 2014, there’s usually a reason.

In the hip, up-and-coming Salesas neighborhood, across the street from the recently reopened (and equally lively) Barceló food market, Madrid’s first five-star boutique hotel looks, from the outside, like many grandes dames: ornate, decadent, and just a bit over-the-top. Inside is another story; while many of the original details (hand-painted azulejo tiles, grand marble staircase, stained-glass windows, windowed wooden elevator) have been painstakingly restored with the help of local craftsmen, the style is undeniably contemporary, with even a hint of Scandinavian-inspired minimalism to offset the pull of the antique. This devotion to design alone would have merited the aforementioned buzz, but Obrador and his team didn’t stop there, throwing in one of Madrid’s most innovative restaurants, most soothing spas, most understatedly cool bars, and, of course, the superlative service required of any five-star stay.

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.

Since it opened in 2009, the Aria Resort & Casino has been a leading example of the post-kitsch, post-theme-hotel era of Las Vegas luxury accommodations. As the 61-story centerpiece of CityCenter—a cluster of hotels, residences, and shops on the Strip—the Aria impresses with its scale, its up-to-date technology, its glass-and-light favored design, and, for a hotel with 4,004 rooms to look after, its surprisingly good service. Even the Aria’s standard rooms, and their marble bathrooms, are large, and the drapes on its floor-to-ceiling windows know when to open themselves. It also boasts eco-credentials: Along with Vdara, another CityCenter property, the Aria was the first Las Vegas hotel to achieve LEED gold-certified status. Its 150,000-square-foot casino dazzles even those who only occasionally look up from the tables. The nightclub, Jewel, is among the hottest on the Strip. And the video Game Room is state of the art.

Cavell’s Cook Shop hides in plain sight along the road that hugs the shore on Antigua’s southwestern coast. Its humble, nondescript outward appearance bears every likeness of a simple storage shed or roadside workshop. Thick, encroaching foliage on either side further suggest its owner might prefer his or her place to maintain a low profile. The long line of cars regularly parked astride the road outside Cavell’s at all hours of the day, however, tells a different story. So too do the savory aromas emanating from beneath her galvanize roof, and the smiles on the faces of her steady stream of people filing in and out of here. You see, small and simple though it may be, Cavell’s is the prime spot for real local food in Antigua. The sun pounding down on the galvanize roof combined with the heat put forth by the various cooking apparatuses maKe standing inside Cavell’s feel like limin’ in an oven. No one was complaining, though. Cold Wadadli’s and good company have a way of keeping things cool here. Come to Cavell’s with a smile, some patience, and an open mind and you’ll make friends of the broad swath of local Antiguans, representing all walks of life, easily.

Hong Kong has been one of the world’s most important ports for eons. This museum, an especially great destination for families with children, has more than a dozen galleries with exhibits highlighting the importance of the port of Hong Kong to China’s role in world trade throughout history. There are exhibits on sea bandits and on the development of Victoria Harbour. Explore collections of navigation equipment, ship models, nautical paintings, and photographs of traditional Chinese junks. There’s a cool gallery showcasing the sounds of the sea—whistles, bells, horns, the crash of waves, the clank of halyards, the thrum of engines—and another on passenger ships, whether they carry poor immigrants or leisure cruisers. A very realistic bridge simulator will give you a feel for maneuvering a range of vessels, from huge container barges to high-speed boats and even Hong Kong’s famous Star Ferry.

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.

The W Santiago is where the cool kids stay. Which other hotel would dare to have a sign reading “WHATEVER” at the entrance? Since opening in 2009, the hotel has earned a strong following, both from locals and visitors. Dimly lit with a color scheme of purples, greens, and black, the rooms are modern, with full-length windows overlooking the city. Located in Santiago’s financial district, officially known as El Golf, the W is part of a large skyscraper (hotel reception is on the fourth floor) filled with restaurants and shops. The 196 rooms reach to the 21st floor, and the W has arguably the best roof terrace in town (Hotel Noi Vitacura being a close contender). The roof terrace has an infinity pool, knockout city views, and a heli-pad for those who want to whiz off to wine country or hit the ski slopes in speedy style.

This lovely state park stretches along the rugged volcanic shoreline of western Maui, three miles from Hana. It’s best explored on the 2.2-mile hike that starts at the black-sand beach and follows the dramatic coast, passing lava tubes, rock arches, blowholes, and Polynesia’s largest heiau (an ancient Hawaiian temple) along the way. Avoid standing too close to the geysers as well as the lava benches near the ocean, which can crumble easily, and watch out for high surf. If you’re looking to cool down after your trek, take the loop trail to the park’s freshwater caves, where you can explore two separate chambers (the first tends to be clearer and more inviting).

St. Lucia’s iconic twin peaks—Gros Piton and Petit Piton—dominate the island’s scenery, soaring 2,500 feet from the sea on the island’s southwest Soufrière corner. Designated a World Heritage Site along with the surrounding Pitons Management Area, these volcanic spires take every first-time visitor’s breath away. There are various ways to experience the Pitons. The brave hike either peak—Petit Piton is more strenuous, and the trail isn’t marked; Gros Piton has marked trails and is a two- to three-hour hike from the village of Fond Gens Libre. Others opt to take it easy and sail past them on a catamaran cruise, or view them from land along the coast or from the terrace of La Haut’s restaurant. Sugar Beach, facing Gros Piton, offers a frontal view of the peaks as you swim.

The ocean churns as a 36-ton mammal swims up to the boat. With your arm plunged into the cool water, you await the touch of a California gray whale. Like a house cat craving a scratch on the head, the whale pushes its rubbery skin, rough with barnacles and battle scars from boats and orcas, against your palm. From January through March, hundreds of gray whales settle in Magdalena Bay, on the southwest coast of Mexico’s Baja peninsula. From their feeding grounds off the coast of Alaska, they’ve made one of the longest animal migrations—more than 5,000 miles—to mate, give birth, and raise their young here. Visitors who join local fishermen and outfitters in the bay are practically guaranteed to see whales, and the luckiest will encounter “friendlies,” including proud mothers who nudge their wrinkly black calves toward the surface. Sea Kayak Adventures offers a new trip that combines gray whale sightings in Magdalena Bay with blue and fin whale watching in the Sea of Cortez. From $1,495. (800) 616-1943, This appeared in the January/February 2013 issue.

Cuevas del Indios (Indian Caves) of Arecibo offers a tidbit of ancient history of a lost people. An easy-to-find natural wonder, with a simple $2 fee for parking, this you won’t want to miss. Bring some sunscreen and your camera. Begin your hike up sharp and spiky cliff sides (no worries, I was able to do it all in sandals). Work your way up to the top of the cliff and enjoy the fantastic view below. Ocean spray from the massive waves breaking against the side of the rocks will cool you off with a little salty mist. Dare to look over the edge to see a landscape of arches and tunnels, burrowed below your feet. Climb down into the rocks to find a wonderful—and surprisingly well-preserved—variety of Taino Indian petroglyphs. A small climb down a somewhat sturdy, handmade ladder lands you at the base of the cave with stone carved images surrounding you. Now is your chance to experience some history. Wander through the smaller tunnels, and listen to the ocean making its way inside the cave with every massive wave crashing outside.

An hour’s drive from Tórshavn, in one of the Faroe’s northernmost settlements, sits the family-run Gjáargardur Guesthouse of Gjógv, bordered by steep slopes and a natural harbor. With its wooden exterior and traditional, turf-topped roof, it practically blends into the surrounding nature, putting the focus on its sweeping ocean views. Rooms here are modern and spacious, with large windows that look out across the valley, and service is friendly and accommodating. An on-site restaurant serves breakfast, lunch, and dinner during high season, while a gift shop stocks postcards, ice cream, and Faroese woolen jumpers that make for perfect souvenirs. There’s even a small playroom in the basement for children, though most guests are here to hike Slaettaratindur—the highest mountain in the Faroe Islands, which looms over the guesthouse and its namesake village.

Crashing waves serve as the soundtrack to your stay at Elbow Beach, situated on 50 lush acres along Bermuda’s rose-hued southern coast. Decorated with exposed beams, tiled floors, and neutral color schemes, the spacious cottage-style rooms are the portrait of coastal elegance—think coral-emblazoned throw pillows, wicker benches at the foot of the beds, and ocean or garden views through French doors. Polished-pebble paths lead the way to the spa, which offers treatments inspired by local ingredients, from a ginger-and-coconut scrub to a hibiscus bath. Grab a rum swizzle in the lounge, relax by the curving perimeter of the pool, or snorkel, swim, and kayak at the hotel’s private beach. You might also prefer to hit the pavement: Elbow Beach is mere minutes from the capital of Hamilton, Gibb’s Hill Lighthouse, and four 18-hole championship golf courses.

Discreetly tucked away down Dean Street in the heart of Aspen, the St. Regis is a bastion of mountain town luxury. Fresh from an interior remodel (completed in 2012) the property brings urban sophistication to the Rockies. Every guest room features a large marble bathroom with a separate bathtub (perfect for soaking after a day on the slopes). The lobby becomes a social hub in ski season and during big events such as the annual Food & Wine Classic. Order a drink and watch for star chefs as you take in the views of Aspen Mountain. If you’d rather be discreet, sneak away to the Library, and lounge on one of the couches. The signature St. Regis butler service caters to every whim at any hour, from securing lift tickets to scoring dinner reservations. When the weather turns cold, there’s no better place to warm up than the Remède Spa with its hot and cool plunge pools, steam caves, and an oxygen lounge, not to mention some of the best therapists in Colorado.

If you want to check out where the San Diego locals hang out, you have to stop by Bootlegger, located on the border of Gaslamp. The bar itself is unique, with a beautiful stone top and lined with hand-carved wooden panels imported from Mexico. There are comfortable seats no matter where you look. Although the decor is going for that dive bar feel, it’s got a touch of hidden elegance. When you come in, as long as it’s not too crowded, the service is highly personable. The Bootlegger is designed somewhat to look like a 1920s speakeasy, and has some interesting art on the walls. The drinks are poured using top-grade liquors; my favorite so far (pictured) is the ‘Old Fashioned'—Bulleit Bourbon, Angostura bitters, sugar, fresh lemon and orange peel. They have a good number of beers on tap and a great selection from the local micro-breweries. I recommend the happy hour—it’s not too crowded and select drinks and all appetizers are half price. For a neighborhood bar, the food is really good. The Bootlegger bar is a great place to experience the San Diego vibe. Another cool thing is that they don’t allow smoking out on the patio around the bar, so if you want to enjoy a smoke-free night, this is the place to be. Tip: It gets impossibly crowded during any game going on at Petco Park, which is the local baseball stadium. During the late week to weekend it also gets crowded. If you want to come and chill before a night on the town, come by for the happy hour, from 3–8 p.m.