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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.

More than any other of the luxury beach-colonies that opened in Jamaica in the 1950s, Tryall has retained the feel of a private club. Yet this 2,200-acre property, with 87 villas, almost all having views that sweep down to the Caribbean, is Jamaica’s largest all-villa resort, and home to one of the Caribbean’s finest golf courses. Created by a group of Texas investors that included a future governor (John Connally) and future senator (Lloyd Bentsen), the resort, backing its own private beach just west of Montego Bay, continues to add villas notable for their luxury and individuality, one with a gallery devoted to Jamaican art, another with its own basketball court. Each villa has a dedicated staff, including a chef, housekeeper, butler, laundress, and gardener. And although each villa is essentially self-contained, the resort’s restored 1834 Georgian Great House, with its restaurant and bar, where events such as the manager’s cocktail party are held, serves as focal point for guests who want to “get out” without leaving the property.

This 12-cottage luxury hotel, 3,100 feet up in the Blue Mountains, is Jamaica without the beaches. It is the Jamaica of misty mornings, cool, cuddle-worthy evenings, and a musical heritage recognized worldwide. First as a private estate belonging to music producer Chris Blackwell and then as part of his Island Outpost collection of hotels, Strawberry Hill has been a creative refuge for performers including Bob Marley, the Rolling Stones, and Willy Nelson. After Hurricane Gilbert destroyed the estate’s great house in 1988, Blackwell commissioned Jamaican architect Ann Hodges, who specializes in historic reconstructions, to build the cottages, a restaurant, and a pool, which were opened in 1994. Yet despite the rock and roll history, and the hanging with like-minded souls up in the mountain mists, what guests seem to remember most is the far-below views of Kingston, especially at night, when the lights glow and sparkle from what must certainly be another world.

The Inca Trail is perhaps the most famous trek in Peru. This is the road to Machu Picchu, an ancient route that leads from the Sacred Valley into the heart of the Andes. You must obtain a permit and hire an official guide in order to hike the Inca Trail proper. There are plenty of tour operators in Cusco that offer trips up to Machu Picchu, so you should definitely look at reviews before you choose. For better or for worse, the tours are all-inclusive. The local tour operators employ porters to carry your packs and set up a camp. A team of local chefs will prepare three meals a day, and many hikers come back raving about the delicious meals. Keep in mind that the trek can be tough, especially in the first few days. The trail is often narrow, and it flirts with formidable heights. The mountains in this part of the Andes can rise well over 13,000 feet, and many hikers find themselves suffering from altitude sickness. Make sure to take a few days (in Cusco or the Sacred Valley) to acclimatize before you begin the journey. Finally: make sure to plan ahead! The Peruvian government limits trail access to 500 people per day, including porters. This regulation protects the local ecosystem and the delicate ruins, and it ensures that the trail won’t be too crowded. However, it also means that permits for the peak summer season sell out months in advance. If you aren’t able to get a permit for the classic Inca Trail, never fear: there are various other trails that lead to Machu Picchu.

No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a harmony of design and setting is the result. The feel is rustic, but not rough (the showers might be outdoors, but the rooms are air-conditioned), and the feeling carries over to the pool, which sits on a rock platform halfway down the cliff face, from where sunbathers can don snorkel and mask and clamber down into a usually calm Caribbean. Even the restaurant hangs over the water, adding emphasis to the promise of dishes being fresh from the sea.

As does practically every hotel in Jamaica, Rockhouse has its celebrity stories, going back to the early ‘70s when Bob Marley, Bob Dylan, and the Rolling Stones added their names to the guest register. But it wasn’t until 1994, when a group of Australian owners took over, that Rockhouse began to evolve its reputation as one of the most Jamaican of Jamaican hotels. It happened in part because Rockhouse has none of the formality that some of the island’s best-known hotels, with their British colonial roots, still possess. And in part because of its active role in funding local education projects, it’s a valued, and popular, part of the community. That, and the restaurant’s homemade jerk sausage is legendary.

Cape Town already feels like it’s at the tip of the world, but the sensation is magnified at Tintswalo Atlantic, where guests get cozy in suites just a few feet from the ocean. Park in the lot just off famed Chapman’s Peak Drive and take the hotel van, which winds its way down a steep road and drops guests at a collection of semi-detached units. Each is themed after a different island—Zanzibar, Antigua, Sicily, and, oddly enough, Robben (where Nelson Mandela was imprisoned). The details are thoughtful, however, from the elaborate, wood-carved headboards to the seashell-encrusted bathroom walls and idyllic paintings. It’s hard to find a setting more romantic and remote. In the unlikely event that you want to venture out, there’s a shuttle that whisks guests to Cape Town, just over 30 minutes away.

This tiny hideaway overlooking the sea near Port Antonio originally served as a live-in recording studio for performers such as No Doubt, Alicia Keys, and Amy Winehouse. Although recording sessions still go on, Geejam is now a seven-room hotel, its guests often honeymooning couples acting out fantasies having nothing to do with rock and roll. Geejam’s cabins, especially, are very private, and guests sometimes spend days taking meals on their veranda and splashing in their outdoor Jacuzzi without being seen by anyone but the staff, who appear only when called. Of course, who wants to stay hidden forever when the Bushbar restaurant promises convivial chitchat, an occasional game of pool, and even live music? Not to mention that the hotel beach, in a cove across a road at the bottom of the property, promises four-poster sunbeds and, yes, Wi-Fi.

Set within a century-old, Pantheon-inspired former bank building, the Ritz-Carlton, Philadelphia raises Center City living to classical heights. When the building opened in 1904, the Girard Trust marble dome was the largest in the country, and its columns and styling matched its inspiration down to its oculus 142 feet from the floor, the exact height as the Roman original. Today, every stay starts in this grandiose rotunda, where staff man the immaculately preserved bank-teller booths. Guest rooms and suites are in the attached 30-story office tower, gutted and transformed into a hotel by Ritz-Carlton.

All 299 rooms and suites bring classic Ritz-Carlton elegance, with wood furnishings matching gold, sage, and pumpkin hues. High ceilings and picture windows with stunning city views enhance the vibe, while spa-style marble bathrooms have rain showers.

The bustling corner of Walnut and 17^th streets is anchored by the Latham, a stone-and-brick tower built in 1907 as luxury apartments for moneyed Philadelphians. While other Center City historic structures met their demise in the late 1960s, a group of investors doubled down on the stately building, transforming it into Philadelphia’s premier business hotel in 1970. The prestigious address completed a top-to-bottom renovation in 2011, bringing the Latham firmly into the 21st century while preserving period artifacts and style.

True to its apartment roots, arriving at the hotel is more like entering a tony doorman building, and the Latham’s residential roots bestow spacious guestrooms with tall ceilings, bay windows, and big bathrooms. Gold and gray hues are complemented by pops of blue, while big bathrooms keep it simple with a tub/shower combination.

The Morris family’s roots are among the deepest in colonial Pennsylvania. Anthony Morris settled here in 1685 and would become one of the city’s first mayors. A century later, his grandson Samuel served as a captain of the Continental Army’s Philadelphia City Calvary. Though the Morris family’s red-brick mansion on 8^th street was built in 1787, it upholds a pre-Revolutionary colonial style epitomized in the stately Independence Hall, and members of the family would live in this large corner property for the next 120 years. A painstaking restoration in the mid-1960s earned it a spot as a National Historic Landmark, and the current owners renovated the property in 2000, transforming the distinguished address into a 17-room boutique hotel without compromising original architectural details. With a leafy courtyard garden, gourmet farm-to-table restaurant, and a focus on personalized service, the latest incarnation of this home lives up to its storied past.

Each room is tastefully decorated in Colonial-era decor and reproductions. Despite the history and limitations inherent in any historic structure, guestrooms are large and uncluttered with all the modern conveniences, splashes of natural light, and sparkling bathrooms, some with Jacuzzi tubs. Adding to the allure are a complimentary continental breakfast and a cocktail, beer, or glass of wine on the house.

Where in Montreal can diners hope for an affordable meal that isn’t drenched in oil or entirely free of flavors? At L’Gros Luxe, that’s where. This stylish neighborhood watering hole may look like a hip, Victorian-inspired and overall super cool place but the truth is that anyone is welcome; from ladies who lunch, young families who brunch or friends out to celebrate a birthday. Portions at L’Gros Luxe are smaller than a regular meal but bigger than tapas, and yet prices are always under $8 per plate. L’Gros Luxe strives to bring its customer the freshest, locally-sourced produce available, and the way they can afford to cut back on prices is by making literally everything in house - from sauces to veggie patties from scratch. Their poutine is quite a mouthful - tater tots, cheese curds, veggie gravy and green onions. A nice change, and something poutine aficionados should not deprive themselves from. Their legendary Ceasars, which are topped with a mini grilled-cheese, are simply mindblowing. And easy on the wallet.

The Palacio Duhau Park Hyatt is a true palace. Built by an English Argentine railway executive, this Tudor Revival mansion dates to the late 1800s. The Duhau family, which bought the property in the 1920s, added an additional neoclassical building modeled after Le Château du Marais outside Paris. The property sat empty for a few decades at the end of the 20th century until a local developer partnered with Hyatt to turn it into a hotel. After a $74 million renovation, they helped preserve much of the original artwork and red marble flooring, invigorating the once faded Belle Epoque elegance. A larger, sleek tower with modern guest facilities was also added.

The property today is a testament to the grandeur of the most European city in the Americas. There are crystal chandeliers, intricate ironwork, and travertine marble bathrooms. There’s a bar where one can indulge in cigars and brandy, after, of course, dining at one of several high-profile restaurants with wine cellars designed to impress even the most hard-core oenophile.

Zurich’s Old Town has one foot firmly in the past and the other very much at the forefront of Swiss culture. Wandering through the pedestrian-only cobbled streets of the Altstadt (which you can do for hours!), you’ll find Switzerland‘s highest concentration of clubs, as well as theatres, comedy troupes, street performers and young fashion designers selling their wares in small, elegant shops on medieval streets. Landmarks include the Grossmünster’s double towers, built by Charlemagne, and the Peterskirche, which has the distinction of being the church with Europe’s largest clockface. Don’t miss Limmatquai, along the Limmat River, one of Zurich‘s most thronged shopping sites where restaurants and shops are housed in Baroque gilded houses from the 1700s, something like the canalside houses of Amsterdam. It’s a great place to actually walk into the past and have the vibrant present all around you! Check out the Artistry and Craftsmanship itinerary to Switzerland, created by Bob Preston of Swiss Panache, on AFAR Journeys.

The 40-room John D. Rockefeller estate is sometimes described as being modest compared to other Gilded Age mansions on the Hudson. While it is true that it doesn’t have the same over-the-top quality of the Vanderbilt mansion, it does have one thing that distinguishes it from the other estates nearby, its gardens. Laid out at the beginning of the 20th century with Frederick Law Olmsted (of Central Park fame) leading the project briefly before being replaced by William Welles Bosworth, the gardens are one of the best examples of Beaux Arts garden design in America. Bosworth’s design consists of a number of different gardens spread over terraces descending from the house, many with views of the Hudson and the Palisades on the other side. (The Rockefellers helped protect the land on the opposite side of the river, assuring their views would never be ruined.) Japanese, French, and other styles are contained in separate garden rooms, while the grounds are also home to a number of contemporary sculptures, fitting given the Rockefellers’ legacy as patrons of the arts. It is only possible to visit Kykuit on guided tours offered from the beginning of May to the end of September. (Members of the Rockefeller family continue to use other buildings on the estate and they are apparently not interested in having visitors wander away from Kykuit and drop by unannounced). Choose the “Landmarks Tour” if you are interested in spending more time in the gardens than the house itself.

This small, chic hotel came into being after an Argentine PR director and her English record producer husband couldn’t find the perfect place for their visiting guests to stay during their Buenos Aires wedding. They needed a place with a bar, a spa, a nice pool, good cocktails in a friendly environment—and so in 2005 they opened Home, one of the pioneer boutique properties in Palermo Hollywood. Strategically located within blocks of much of the city’s nightlife, Home has become something of a base for those coming to the city looking to indulge in it.

Generally though, Home’s reputation is quite positive. Few modern design elements have been left out, from Knoll furniture and vintage wallpaper to the Chilean wool rugs and tech-friendly amenities like iPod-ready stereos and LCD TVs. A spacious walled garden area is the focal point of the property, holding the heated swimming pool plus deck chairs and ferns, alongside a bar and restaurant.