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The beloved Dar Ahlam resort has taken its show on the road with Route du Sud, a six-night driving tour to five destinations with three private retreats that showcase the shape-shifting landscapes of isolated southern Morocco, one property at a time. The first stop is the hillside Maison des Arganiers, two and a half hours from Marrakech, in a rocky landscape facing miles of argan groves; next comes La Maison de l’Oasis, nestled in an oasis of palms; and the final private destination is the dramatic La Maison Rouge, which sits at the edge of a red canyon. Along the way you have beach picnics, nomadic campouts, and scenic drives through dramatic desert dunes.

The Four Seasons earns its five stars for everything from its location—smack in the middle of Seoul’s most-visited palaces and landmarks—to its detailed amenities, such as customizable mattresses. Rooms overlook Gyeongbokgung Palace, the largest and arguably most beautiful of the royal residences, or Cheonggyecheon stream, each a few minutes’ walk from the hotel. Its seven restaurants and lounges include a two-level sushi and sake bar, a Michelin-starred Cantonese restaurant, and an exotic cocktail bar hidden speakeasy-style in the basement. The massive wellness center combines traditional Korean spa rituals with personalized beauty treatments and a 24-hour gym with panoramic views. An indoor pool and saunas, a virtual golf simulator, and a Lego kids’ lounge provide something for every guest.

Opened in 1946 as a restaurant (where the famous regulars included Churchill and Hemingway), La Maison Arabe later expanded to a small hotel, then grew again under its current French-Italian owner. Today, it features 26 garden- or patio-view rooms and suites, individually designed in either a traditional or slightly more modern Moroccan style. All have air-conditioning and heating (a must for the varied desert temperatures) as well as Wi-Fi, satellite TVs, and marble-and-granite bathrooms stocked with aromatic toiletries. Also available to guests is an idyllic swimming pool, around which the hotel serves a home-cooked breakfast each morning, and the clubby, 1930s-inspired Piano Bar, where guests can enjoy live jazz and pre-dinner drinks by the fireplace. When it’s time to unwind, head to the cozy spa for an array of face, body, and hamman treatments, all performed with products made exclusively for the hotel.

Much like in the past, La Maison Arabe revolves around food. Guests can choose between Le Restaurant, where a gorgeous fountain and hand-painted ceiling set the stage for authentic Moroccan fare, and the intimate, lantern-lit Les Trois Saveurs, which serves a sophisticated menu of French, Moroccan, and Asian dishes. Additionally, the hotel offers some of the city’s best cooking classes, which are open to outside guests. Led by a dada (a traditional Moroccan cook), the lessons take place either at the main hotel or the Country Club—a satellite property located 15 minutes away by complimentary shuttle, where students can also find a larger pool, lush gardens, a restaurant, and a bit of calm away from the bustle of the medina.

Put on your comfortable shoes and head to the many trails of Cayman Brac to see wildlife, as well as scenic and geological sights. There is a path for all skill sets. Listen to the mating calls of the parrots flying above at the National Trust Parrot Reserve Hiking Loop, or descend carefully into Peter’s Cave and move through the various layers to discover a truly breathtaking natural wonder. Most hotels have a brochure of all the hiking trails; this includes images, difficulty, and a brief description of each trail.

A Greek Revival family mansion built at the turn of the 20th century, Hotel Ella owes both its name and its grandeur to its very first lady of the house, Ella Wooten. Known for her impeccable style and grand tastes, Ella was a fixture of Austin high society who hired the stone carver responsible for the Biltmore Estate to craft her house’s columns and verandas and worked with Neiman Marcus’ Stanly Marcus to redecorate the interiors in 1925.

Nowadays, Hotel Ella pays homage to her good taste with fashionably understated decor, a locally sourced restaurant, and an art collection that the original proprietress would have coveted. Works include original Ansel Adams photographs and Wooten family portraits and jewelry. The owners pride themselves on making guests feel just as pampered as Ella might have, with perks like a free town car service—even though the hotel is within walking distance of downtown—and a concierge team for whom no request is too much.

Hands down the best place to stay in Mexico City’s Centro Histórico is the aptly named Downtown. Located inside a restored 17th-century casona (mansion), the hotel shares its property with a select group of Mexican businesses, including a chocolate boutique and a mezcal bar, as well as restaurants, cafes, and fashion and jewelry ateliers. Appropriately, rooms evoke a bygone era, with low lighting, brick ceilings, and tile floors somewhat reminiscent of a monastery. Amenities are spare but select (C.O. Bigelow toiletries, for starters), and service is unobtrusive but attentive. After a day spent exploring the city, head to the rooftop pool and bar, where you can sunbathe on a bright yellow chaise lounge or sit under an oversized umbrella while waiting for your cocktail to arrive.

“Buongiorno, Signor Farley,” said Umberto, the head waiter at Hotel Missoni’s Cucina restaurant. By the beginning of the third day of my stay, the staff knew my name. And what I drank with breakfast. An espresso doppio was delivered to my table a minute later. “Prego,” the server said.

You’d think I was in Italy. In fact, I was 2,500 miles southeast of the country’s heel, in the capital of diminutive, oil-rich Kuwait. Opened in spring 2011, Hotel Missoni, owned by the eponymous fashion and home furnishings house, is one of many designer-conceived hotels that have popped up around the globe.

I have to confess: I have a complicated relationship with fashion. Maybe it’s related to my childhood. (Isn’t everything?) In the seventh grade, I wore a T-shirt to school that read, “My Son Is in the Navy.” My trend-conscious peers, who clearly had no sense of irony, laughed at me until the final bell rang. When I wore bowling shoes to high school, I was similarly mocked. How would I do in a hotel designed by a couturier?

I was picked up at the airport in Kuwait City in a Maserati (a complimentary perk for all Missoni guests). Not a bad start.

The property (like its sister hotel in Edinburgh, which opened in June 2009) is the brainchild of the Missoni family matriarch, Rosita. The hotel’s 169 rooms were designed to feel like her home. Compact Hans Wegner wishbone chairs and tuliplike Eero Saarinen–designed tables rest on hardwood floors, and everything—espresso cups, towels, even the swimming pool—displays the colorful striped patterns Missoni is known for. Generous helpings of turquoise, gold, and beige are splashed throughout the hotel to evoke the bayfront landscape outside, and every room looks out on the ever-expanding Kuwait City skyline. Like many things Italian, the hotel is simple and comfortable.

The Missoni team, which is fine-tuning its approach before opening hotels in larger markets, learns fast. There are no design hotel clichés here: no faucets with the function designed out of them, no overly formal staff. “Are those Camper shoes?” a waiter asked me one day at breakfast. I nodded. “Like bowling shoes,” he said. “Very cool.” Here, it seemed, fashion and I got along great.

965/2577-0000, from $414. This appeared in the September, 2012 issue.

Taking a nighttime stroll through Brooklyn, retracing George Washington’s footsteps as he was engaging British forces in Brooklyn and Long Island who went on to invade New York City in the summer of 1776 during the American Revolution (I love a good dose of American history). I paused for a moment to admire the ingenuity and design of the Brooklyn Bridge as well as the Manhattan skyline. Then I found myself humming Alicia Keys’ “Empire State of Mind.”

The Sunriver Resort is near Bend, Oregon, which is a rightfully famous, and incredibly beautiful, area for outdoor adventure. In the winter, there is skiing at nearby Mt. Bachelor (25 min away), but the summer has even more to do, including golfing, hiking, mountain bike riding, tennis, and of course, swimming in the resort’s amazing pool, which has a water slide, sand play area, hot tub, and amazing views of Mt. Bachelor and the golf course. The rooms are up to date and nicely appointed. The main lodge has a great bar area, a nice restaurant, and a large “back lawn” with live music and kid-friendly activities. Overall, a highly-recommended place for a family vacation.

With its own shuttle flight service from St. Lucia and Barbados and an unbeatable location on one of the Caribbean’s most picturesque stretches of sand, Bequia Beach Hotel is an island unto itself. The 10-acre property, easily Bequia’s most luxurious, also includes a spa, two swimming pools, two restaurants, and a canvas-tented bar on nearby Princess Margaret Beach, plus 56 individually appointed rooms and suites furnished in an eclectic, island-chic style (think red four-poster beds, wicker armchairs, and palm-accented throw pillows). Adventurous types can take advantage of the hotel’s free sports equipment (including kayaks, paddleboards, and bikes), while those who prefer more subdued activities can opt for complimentary yoga classes.

With 394 rooms, there’s nothing understated about St. Kitts Marriott Resort. What it lacks in intimacy, however, the hotel makes up for in fun amenities, like umbrella-shaded chaises perched on the golden sands of North Frigate Beach, and a meandering pool that resembles a lazy river. On the grounds you’ll also find an 18-hole championship golf course, volleyball nets on the beach, and a 15,000-square-foot spa that uses local botanicals like jasmine and frangipani in its treatments. When you need to get out of the sun, there are eight restaurants serving local specialties and global favorites, as well as a lively casino.

Southwest of Anguilla is one of the island’s top three beach areas: the two-mile-long brilliantly white stretch at Rendezvous Bay. Its long shore, steady breeze, and calm Caribbean waters provide a break from the crowds at Shoal Bay and Sandy Ground. The western end does offer some fun daytime beach-bar action, which grows rowdier at night and on the weekends, when the famous Bankie Banx’s Dune Preserve venue attracts residents and visitors for live music. You can view St. Martin, across the channel, from shore.

A chic deli to be sure, Belmondo serves American-style sandwiches like Reubens, tuna melts, grilled cheeses, etc.—about which its young, fashionable adherents rave—but the menu holds some surprises as well, like a barbecued brisket or a chicken curry on peasant bread. The salad selection is varied and creative, in everything from an old-fashioned Cobb to exquisite local beets with goat cheese and avocado. Breakfast (weekends only before 1:45 p.m.) is also about greatest hits; think eggs Benedict and French toast or one of the very few bagels with gravlax you’ll ever see south of the Rio Grande. The place, in Roma Norte, is famed for celebrity sightings and generally crowded, yet the vibe is low-key, cool, and friendly.

Fontana di Trevi is, as it should be, one of the most visited landmarks in Rome. Seeing it is worth the blind stumble through narrow stone streets and alleyways. But do so at night (and in the rain, if possible) to be rewarded with the stunning sight of the immense baroque fountain lit before a dark and shining background, like a scene from a Fellini movie. This is when the Trevi Fountain is at her most beautiful and most magical self.

At the end of a secluded peninsula, right on Coco Point, which is Barbuda’s southernmost tip, Coco Point Lodge is one of only a few modern hotel resorts on the island. Although not five-star fancy, this all-inclusive property, is plenty comfortable offering a mix of rooms and private cottage rentals in small buildings scattered across the grounds. Bordered by some 2.5 miles of gorgeous white sand beach and safe, reef-protected swimming in the clear turquoise waters of Cocoa Bay, it is a good choice for active types as included activities feature everything from sailing to snorkeling, waterskiing to windsurfing and sea kayaking. Deep-sea, reef or bone fishing expeditions can also be arranged, as can day trips to the Frigate Island Sanctuary for birds.