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For those who aspire to travel as trendsetters in Jamaica, it helps to know that Port Antonio, way out on the eastern end of the island, is the destination to head for. And the address to shelter at is the Trident Hotel, whose 13 waterfront villas would not look out of place on South Beach. Nor would the crowd that hangs around its infinity pool or in its restaurant, Mike’s Supper Club, where local musicians and the occasional celeb sit down to knock out tunes on the 1917 Ferrari-red grand piano. The Trident Castle, a kind of fantasy annex, is a former private residence whose grand rooms, sea-view terraces, and dollhouse-size chapel make it ideal for destination weddings. A hard road to get there? Not for guests who avail themselves of the helicopter pad.

It’s a sad fact that many swaths of Johannesburg aren’t exactly walkable, but that’s not the case at Melrose Arch, a trendy complex filled with some of the city’s hottest restaurants, galleries, and shops. Guests are in the heart of the action if they book a stay at the African Pride Melrose Arch Hotel, a slick property with 118 stylish, contemporary rooms adorned with modern African art. And now that the hotel falls under the Marriott family umbrella, guests can expect all sorts of perks and upgrades associated with the brand.

Siem Reap’s emergence as a somewhat unlikely destination for fashion lovers is largely due to the efforts of one individual: Madagascar-born Eric Raisina. Inspired by the Khmer artisanal silk weaving he witnessed on a trip to Cambodia back in 1996, Raisina decided to base himself in the country and hasn’t looked back since. He opened his original haute couture outlet in 2005, and his daring designs, colorful and often inspired by ancient Cambodian culture, have earned acclaim worldwide. Admirers of his work can find it for sale at two locations in Siem Reap: at his couture house on Charles de Gaulle Avenue and at the FCC Angkor hotel.

Surrounded by swaying palms, tropical flowers, pink sand, and sapphire waters, the 100-acre Fairmont Southampton is Bermuda’s ultimate luxury destination. The 593 rooms and suites are among the largest on the island, and feature marble baths stocked with Le Labo products and private balconies that look out onto the Atlantic Ocean, Great Sound Harbour, or the lush landscaping of the on-site Turtle Hill Golf Club. A pool, beach club, dive center, kid’s camp, and tennis courts—plus that 18-hole championship course—offer plenty to keep guests busy. If you prefer to kick back, opt for a lavender-oil massage at Willow Stream Spa, a sprawling space complete with a well-stocked health club, sauna, and steam rooms, or grab a sundowner at one of the resort’s 10 restaurants, bars, and lounges.

The Edgewater made its mark in Seattle history as the place The Beatles stayed when they came through on tour in 1964. Other rock stars (and those who like to travel like rock stars) have since stayed at the Edgewater, choosing it for its singular location on Pier 67 perched over the waters of Puget Sound. The public spaces make design references to the Pacific Northwest, with natural wood and stone everywhere. Waterfront rooms have sunset views that are nothing short of spectacular, and all the rooms are well-appointed, with gas fireplaces and spa-style bathrooms.

Everyone who visits Santa Fe walks along the famed Canyon Road. Originating as an old footpath that once accessed water, it now primarily showcases an expansive range of shops and galleries with Native American art and landscape paintings. A stroll is not complete without a stop at one of the award-winning restaurants, a la Geronimo and the Compound.

Soaring more than 1,600 feet into the air, Taipei 101 is one of the tallest skyscrapers in the world and probably Taipei’s most iconic site. For a small fee, visitors can spend time on the observation deck—a large space that offers a 360-degree view of Taipei. From here, you can get a better understanding of the city and how it is organized. For that reason Taipei 101 is the best place to start your sightseeing adventures. There are also a number of great restaurants in Taipei 101 along with shops and entertainment options; you can plan at least half a day of experiences at this one site.

Cap your trip to Machu Picchu with a pisco sour on the Orient-Express train ride back to Cuzco. After boarding this luxury train for dinner and the return journey, everyone meets in the bar car for a drink. Live music, the rocking of the train, and the excitement from just experiencing Machu Picchu is a buzz to remember. Soon all the passengers are dancing as they travel through the steep mountainsides under the stars. —Lauren Maggard This appeared in the August/September 2013 issue. Image courtesy of Orient-Express

For evidence of the “everything is bigger in Texas” trope, look no further than this urban resort, which—with 1,606 Asian-accented guest rooms and suites spread out over 45 acres—is one of the largest in the south. Its location in the Design District, not far from the Dallas Convention Center and the office towers of downtown, makes it popular with the business-meeting crowd (as does the 600,000 square feet of on-site event space), but there’s plenty to tempt leisure travelers, too. Paired with an outdoor sculpture garden, more than 1,000 international works displayed throughout the property make up one of the biggest hotel art collections in the world. Guests can dine on everything from steak and seafood to pizzas, salads, and grab-and-go snacks at the eight restaurants and bars, or make a night of it with specialty cocktails and fine wines. They can also relax with treatments at the VSpa, or work off indulgences at the whopping 80,000-square-foot Verandah Club & Fitness, equipped with indoor and outdoor pools; basketball, squash, and racquetball courts; a cross-training and boxing gym; and more. In the summer, the sprawling Jadewaters pool complex—with lazy river, swim-up bar, 180-foot water slide, and kids’ activities—is as close as you can get to a water park in the heart of the city.

Last week we spent 5 days in Copenhagen, Denmark. October is, for me, the best time to visit. It’s colder and there are more chances for rain but the number of tourists is drastically lower. I did not feel suffocated by them at all. Nyhavn harbor was almost empty every day. I love traveling in the shoulder season.

Just inland from Ensenada, Baja California exists a wonderland of fine wine, haciendas and Provencal restaurants. There is an energy here that is worth dawning the bullet proof vest and heading a couple hours south of the Mexican boarder to check out the excitement and culinary innovation. In the Valle de Guadalupe wineries and restaurants are redefining where fine wine comes from and what Mexican cuisine can be. The Valle de Guadalupe sits in a valley that warms through the day and is cooled every evening by the onshore flow off the ocean, allowing perfect conditions for grape growing; which has been going on here for over a hundred years. Additionally, the valley is a source of fine olive oil, locally grown herbs and produce, local farms and seafood from the nearby ocean. The best way to experience this culinary movement is to stay at a winery like Adobe Guadalupe or Vinedos Malagon in the heart of the valley. These wineries offer more than just wine tasting and luxury, they offer activities, ranging from horseback riding to cooking classes, deep sea fishing or dirt biking. The best part of it all is you can still fill up on classic Mexican tacos and mariscos when the fine dining and wine becomes too much.

Comprised of just 10 suites with distinctly different designs, Palácio Belmonte feels more like a dream vacation home than a hotel. The vibe is spot on, given the backstory: A Frenchman traveled to Lisbon looking for a vacation home in the Portuguese capital. He first saw the building from a taxi and thought to himself, “It has nine windows, just like my home in France. I’ll buy it.” It wasn’t until after purchasing the property that he actually set foot inside and saw just how enormous it was—far too large for him and his family. Thus, he set about remodeling the building (which was originally owned by a noble family in the 1400s) with the notion of converting it into a space for visitors.

Great design is everywhere you look in Denmark—in shops, in homes, in public spaces—and the creativity of its people has long been a source of national pride. This museum, located just around the corner from Amalienborg, was founded in 1890, many decades before midcentury modern became an international sensation. It looks at the history of Danish design over the centuries, taking in everything from furniture to fashion to textiles.

The metal-and-glass ribbon structure of this Frank Gehry−designed hotel—not too far from Bilbao—creates an ethereal silhouette that contrasts dramatically with Elciego’s medieval landscape. Opt for a guided tour to learn more about the history of winemaking in the Basque countryside.

The shiny windows of the JW Marriott Hotel immediately draw the eye in. The 371 room hotel is across the street from the Lenox MARTA transit station and has its own indoor walkway to Lenox Mall, making it even easier to lug your purchases back to your room. Nox Creek Southern Grill is the hotel’s in-house restaurant and serves some of the best breakfasts in the area.