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  • Rum Point, Cayman Islands
    Among vacationers who’ve been coming to Grand Cayman forever, there’s a whole faction that essentially camps out at Rum Point all day every day, and you’ll understand why as soon as you see the place. Tucked away, super low-key, and graced with a ridiculously photogenic pier—its perfectly weathered planks cutting a striking figure against the tranquil, turquoise surroundings—this beach is the ultimate spot for settling into a lounger or hammock between water-sports outings. Rum Point’s namesake booze—which used to wash ashore by the barrel, according to legend—is available in all manner of cocktails here, of course. But order at least one mudslide at its spiritual birthplace: the beach’s beloved Wreck Bar.
  • 590 Ocean Avenue
    No matter what kind of getaway you have in mind, you can find a guestroom to fit at Castle Hill Inn. Rooms in the main house vary in size and décor, but each is kitted out for romance with a fireplace, a king-sized bed, oversized tubs, and windows looking over the water and expanses of lawn. The Turret Suite, a bi-level space, has a bedroom on the first level; on the top floor, a soaking tub on a raised floor takes advantage of the 320° wrap-around windows. Below the main house, the Harbor House’s modern guestrooms feature front-porch views of Newport Bridge and the hotel’s Grace Kelly Beach. At the far end of the 40-acre property, the Beach Cottages and Beach Houses are set along the private beach, offering views that take in both the mansions along Ocean Drive and the wild Atlantic itself. The cottages, slightly smaller and closer to the beach, have peaked ceilings with rafters. The airy Beach Houses, compactly outfitted with galley kitchens, sunny decks, ceiling fans, fireplaces, and curated shelves of books, cast a kind of never-leave spell.
  • 132-140 Rue des Rosiers, 93400 Saint-Ouen, France
    Marché aux Puces de St-Ouen, aka Clignancourt, is Europe’s largest flea market and the city’s favorite place to find a bargain. Exiting the Métro at Porte de Clignancourt, those in the know pass by the counterfeit designer-goods hawkers, avoid the parking lot with camper vans full of cheap goods, and head under the overpass to Rue des Rosiers. Groups of stalls form smaller flea markets, each with its own specialty, so shopping can feel like walking through a museum where you can actually buy things. The market called Serpette draws serious dealers looking for mid-century marvels, but shoppers who head as far as Jules Vallès market may score some true bargains. Of course, this is France, where food matters, so there are plenty of local cafés to choose from. Ma Cocotte is trendy chic, La Chope des Puces has live jazz with moules frites, and Chez Louisette draws a crowd nostalgic for French tunes with its simple steak frites.
  • 79 Carriage House Ln, Philipsburg, MT 59858, USA
    In 2007, hedge fund investor Jim Manley bought a working cattle ranch on the site of a historic silver-mining claim to stake as his bigger-than-life family retreat. In 2010, he opened up the Ranch at Rock Creek, a toy-filled haven in southwest Montana’s Big Sky Country, with 13 houses with one to five bedrooms, luxurious canvas cabins for “glamping,” or a nine-room granite lodge. All are decorated by designer Jet Zarkadas and feature Oriental carpets, deep leather chairs, cow skin and woven Navajo rugs, custom duvet covers, and period Western photos and memorabilia. Despite the remote location and 5,200-foot elevation, all accommodations have landline, working Wi-Fi, and cell phone coverage; some have moose antlers, a private sauna, outdoor hot tub, and indoor copper bathtub.

    Open year-round, the 10-square-mile property encompasses meadows, high country lakes, grassy ridges, and stunning vistas of the Pintler and Sapphire mountains. This self-contained adventureland offers horseback riding; heli-hiking; fly-fishing; river floating; high-tech mountain biking; rope courses; trap shooting; and archery on a 3D course using powerful hunting bows to shoot life-sized models of animals. Weekly rodeo and stagecoach rides underscore the Western theme; in winter, guests cross-country ski, ice skate, and snowshoe on-site. A kids’ club frees parents for spa time and other pursuits.
  • 76 Pitts Bay Rd, HM 08, Bermuda
    Known for generations as the Pink Princess, this legend opened its doors in 1885 and remains one of the largest and most celebrated hotels in Bermuda. Fresh off a $100 million renovation in 2016, the 170 rooms and suites are now what you’d expect from a Fairmont-managed property—clean, modern, and comfortably luxurious, all with water views—while public spaces have been elevated by an exceptional collection of modern art (Andy Warhol, Damien Hirst, and Ai Weiwei are just some of the luminaries who grace the walls). The new infinity pool has gorgeous views over the harbor, the spa offers treatments and fitness classes in partnership with noted brand exhale, and the marina’s water-sports team can organize everything from kayak and Jet ski rentals to paragliding lessons. Guests also have exclusive access to a private beach club on Sinky Bay—just 20 minutes away from the hotel via complimentary shuttle—which features water hammocks and snorkeling-friendly waters. Back at the resort, dining options include the buzzing Marcus, serving signature dishes from celebrated chef Marcus Samuelsson, and more casual options highlighting fresh seafood and local rum.
  • San Pedro de Atacama, Antofagasta Region, Chile
    A short drive outside the town of San Pedro de Atacama, Tierra Atacama has wonderful views of fields and Volvano Licancabur. The hotel is part of the Tierra hotel group owned by the Chilean-American Purcell family (who also own Tierra Patagonia, Tierra Chiloé, and Ski Portillo). The property originally served as a cattle corral, but Chilean landscape artist Teresa Moller has transformed the grounds, preserving the ancient algarrobo and chañar trees and restoring the adobe walls.

    The bedrooms are decorated in natural colors, with local touches like ceramics marching along the sills of the extra-large windows. Animal-skin rugs and alpaca throws provide a touch of warmth for the cool desert nights. You can see the incredible silhouette of Volcano Licancabur from all the rooms, but the Poniente rooms are slightly larger and have better views. There is a friendly communal vibe at the hotel, and upon arrival guests meet with the head guide in the main lounge to choose from the range of group activities on offer each day.
  • Piazza Pitti, 1, 50125 Firenze FI, Italy
    You will likely see Bronzino’s famous portrait of Eleonora (or Eleanor) de Toledo, in the Uffizi, during your visit to Florence. The Spanish noblewoman who became the duchess of Florence in 1539 when she married Cosimo I de’ Medici was unusual for her time, playing an active role in politics and as a patron of the arts. Her patronage extended to garden design, in its infancy (at least in Europe) in the 16th century. Eleonora commissioned the Boboli Gardens behind the Pitti Palace as a green escape from the city; they continue to provide a retreat for travelers today.

    Among the earliest examples of the formal compositions that would dominate garden design through the 20th century, the grounds are dotted with classical statues and fountains while straight axes run up and down the hillside with an apparent disregard for topography. A moment in design history can be experienced first hand here. There’s a feeling that the man who planned the gardens (Niccolò Tribolo) conceived a formal plan and then simply laid it atop the site. Principles of garden design were later to shape city planning. The allées of the Boboli Gardens were early models for grand boulevards leading the eye to distant monuments. One of the pleasures of gardens, however, is that you don’t need to know their histories to enjoy the flowers in bloom or the sounds of birdsong and splashing fountains.
  • 2126 Southwest Halsey Street
    I love all of the McMenamins properties I’ve stayed at over the years on travel through the Pacific Northwest, but I may have a new favorite: McMenamins Edgefield in Troutdale, right at the western mouth of the Columbia River Gorge. As always, the hotel honors the past of the building it now resides in, it has great food and drink, and every inch is covered in whimsical art that demands you have a good time. Historic Edgefield was built in 1911 as the county poor farm, and it’s now a 74-acre hotel and playground, home to award-winning farm-to-table cuisine, a winery, a brewery, three pubs, movie theater, golf course, you name it. With 100 guest rooms and hostel accommodations, the instant you step on the grounds you’ll be able to tell that community and creativity are cherished here. If you’re traveling solo or out on a long trip and looking to save some money on the hotel part, I’d encourage you to look at their rooms that don’t have a private bathroom en suite. Instead, you head to the large, comfy, and private communal restrooms to get cleaned up. Brilliant. This is a great spot to launch your explorations along the Columbia River Gorge, and if you live in the Portland area, it’s a great place to gather for a weekend bike ride, grub with fellow friends, and a few cold pints around the outdoor fire pits when things get cold. With films and live music nightly, it’s hard not to want to just live here forever.
  • A four-kilometer seaside promenade is the perfect place for a stroll at Scheveningen, a beach resort in Den Haag’s wealthy northernmost district. In addition to a sandy beach, colorful esplanade, pier and the Scheveningen lighthouse, there’s a Sea Life aquarium, Pathé cinema, the Steigenberger Kurhaus music theater, Scheveningen Museum and a casino. Trendy clubs, restaurants, surf schools and other water sports options line the wide Noorderstrand (North Beach) boulevard. After a three-year metamorphoses completed in 2013, the beach-side stretch offers the best of sun, sand and surf on Holland’s western coastline. Giant sculptures by the sea add a whimsical touch, while numerous bars and eating establishments provide spots to grab a drink or a meal while watching the action in the harbor.
  • San Juan-Caguas-Guaynabo, PR, Puerto Rico
    This is my favorite hike by far. Cueva Ventana (“Window Cave”) is a beautiful, scenic hole in the side of a mountain that opens up to a lush, green valley down below. You’ll trample through mud, hunker down under low-hanging stalactites, dodge around stalagmites, and never look up (there are bats, of course) while wandering through the cave. All this winding around through two caves leads you to one of the most spectacular views in all of Puerto Rico (but I may be biased). The hike to this cave is half the fun. You climb down into a small opening under enormous, ancient tree roots, and you get the feeling of a tomb raider. But, if you’re claustrophobic or don’t feel up to lowering yourself down a cave wall, there’s an additional path that bypasses the first cave and leads you straight to the easier hike to Cueva Ventana. There’s something for everyone! I’m pretty sure I saw one Puerto Rican woman doing the whole thing in heels. This is a must-visit site for anyone touring the northwest central part of Puerto Rico. Another tidbit is that it’s practically free! You can find the directions on PuertoRicoDayTrips.com, park at the adjacent Texaco gas station. UPDATE (2014): There is now an easier way to access this awesome view! There are now boardwalks for ease of access, and you must pay $11 to tour the site. You get a flashlight and hardhat for safety.
  • Arizona, USA
    If, like most visitors, you head for Tucson between Thanksgiving and Easter, you’re probably seeking sun and warmth while the rest of the country deals with the winter blahs. And you’ll most likely find what you’re looking for. There’s a reason why golfers, cyclists, hikers, and runners flock to southern Arizona this time of year. But, once or twice a decade, the lush Sonoran desert might get a snowfall—it never lasts for long, but every saguaro, ocotillo, cholla, and prickly pear cactus will be edged in ephemeral white. As soon as the sun comes up over the mountains, you’ll start hearing the drip drip drip of the inevitable melting...And by the next day you’re likely to be wearing shorts again. Saguaro National Park, which flanks both the western and eastern edges of Arizona’s second-largest city, is the ideal place to go for a hike in the rare desert snow. The Eastern (Rincon Mountain) division of the park has a hilly eight-mile one-way loop road with access to numerous trails. Drive slowly and yield to the runners and senior-citizen-cyclists-in-spandex with thighs of steel. Get out and up into the saguaro-studded hills before the unlikely landscape disappears...Keep your eyes open for bobcats, mule deer, and the pig-like javelina. (You’re less likely to encounter a rattlesnake in the winter months, but this is still desert wilderness.) And if there’s no snow, you might be treated to spring wildflowers. Don’t forget your sunscreen...
  • Konya, Turkey
    Rumi was born in Afghanistan, spent time in Persia (Iran), then settled in Konya, Turkey when his father was invited there to be a scholar. Rumi became an Islamic scholar himself teaching peace, love, and tolerance. He built quite a following of the educated – who saw him as a wise philosopher – and uneducated – who saw him as a prophet. Rumi’s life changed when he created an intense friendship with an older, wandering mystic -- Shams of Tabriz. Shams was a brilliant outcast and Rumi was deeply drawn to a learning relationship with this man who was ultimately supposedly killed by some of Rumi’s fans due to the influence he was having on the younger Rumi. From this tragedy, Rumi found a deep well inside himself filled with an ability to channel poetry. It was about this time that he also introduced the experience of divine harmony that comes from whirling. Thus, a new form of religious ecstasy was created and the Whirling Dervishes (also known as the Mevlevi order) have been doing this annual ceremony marking Rumi’s death for almost 750 years. This is the start of the Sema (ceremony) with each Semazen (dancer) bowing upon arriving on stage and the Basi (the leader) at the “head of the class.” The mesmerizing ceremony represents man’s journey to the oneness of perfect truth – amidst separation and longing - through the power of divine love. In 2005, UNESCO proclaimed the “Mevlevi Sema Ceremony” as amongst the Masterpieces of the Oral and Intangible Heritage of Humanity.
  • 18 Marina Gardens Dr, Singapore 018953
    With its domed greenhouses of epic proportions dotted across some 100 hectares (250 acres), the sustainable Gardens by the Bay are educational and fun. The Cloud Forest is a misty, 42-meter-high (138-foot-high) “mountain” that re-creates tropical highlands; visitors use ramps to explore around and through them. A biosphere of Mediterranean and desert plants, including huge baobab trees, makes up the Flower Dome. Outdoors, guests walk on suspended walkways between steel-frame “Supertrees” that are covered in solar-powered lights.
  • Hoàn Kiếm Lake, Hang Trong, Hoàn Kiếm, Hanoi, Vietnam
    A couple of blocks west of the Sofitel Legend Metropole Hanoi, Hoan Kiem Lake—meaning Lake of the Restored Sword—is one of Hanoi’s anchors. It contains a number of sites worth visiting, like Ngoc Soc Temple and the picturesque, red-lacquered Huc Bridge. The greatest fun here is people watching, from men and women jogging round the perimeter to retired folks doing tai chi or dancing. Many locals come to socialize or just take a few moments to escape the city’s chaotic roads and traffic. Visit in the morning as the city is waking up and the air remains blissfully cool. Photo by Binder.donedat/Flickr.
  • Piazzale Michelangelo, 50125 Firenze FI, Italy
    One of the best views of Florence can be savored from the Piazzale Michelangelo, a short walk across the Arno River from downtown Florence. For a fun afternoon head to the square and enjoy an enchanting panorama of the city, followed by a relaxing alfresco lunch at one of the nearby restaurants. The Piazzale Michelangelo is also worth a visit at night to get a very different glimpse of Florence. The lights of the Duomo and the buildings surrounding it make for a magical nighttime scene.