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On the still-bucolic site of a former coconut plantation just west of Montego Bay, Round Hill is another of the legendary hotels created in the early 1950s to accommodate wealthy Brits and Americans who were discovering the pleasures of a Jamaican winter. Since then, it has evolved into a thoroughly modern resort that manages to retain its original, exclusive, clublike spirit. In the beginning, Round Hill consisted of a group of shareholders (British playwright Noel Coward was one) who rented out their private villas when they were absent. That’s how it still works, although the celebrity shareholder most mentioned these days is designer Ralph Lauren, who rents neither of his two villas. Along with 27 other villas, which can be divided into 86 suites, there’s the Pineapple House, a seafront block of 36 rooms, all decorated, predominantly white on white, by Lauren. The ambience is quiet luxury, the service is relatively formal (the doorman wears white), and the children among the guests are treated as the heirs and future holiday decision makers that they are. Almost every villa has a story, whether it has to do with Coward, the Kennedys, or How Stella Got Her Groove Back. And Montego Bay, whose city lights can be seen only from the highest villa (#28), is still another world away.

Built in a former auto garage in Nashville’s Gulch neighborhood, this five-room boutique hotel replaces industrial vibes with low-key sophistication: The whitewashed rooms—some with loft-style living spaces—feature high ceilings, custom furniture, and high-end amenities like Sferra linens and Turkish cotton robes, and the subway-tiled baths gleam with vintage taps.

There is no front desk, but guests receive a passcode for the entry keypad before arrival, and a concierge service is always on call. Have some down time? A comfortable sitting area is set up with board games and a large sideboard stocked with complimentary refreshments and coffee throughout the day, which makes the 404 the perfect spot for urban explorers who like to come and go as they please. But don’t miss dinner at the 404 Kitchen. Housed in a shipping container and accessed through another keycode doorway, it’s one of the city’s top restaurants.

Don’t let Portland’s low-key, outdoorsy-hipster vibe fool you: the Heathman Hotel is as grown-up and refined as they come. Opened in 1927 as an expansion of one of the city’s grande dame hotels, the Heathman continues to set the standard for classic luxury in the City of Roses. Rather than rest on its laurels, though, the hotel has consistently upped the ante, collecting a museum-worthy array of modern art (including a handful of Warhols alongside works by acclaimed local artists), boasting one of the most impressive collections of autographed books in the world, and offering guests a choice of mattress in the sumptuous rooms. Indeed, so famously decadent and romantic is the Heathman, with its award-winning restaurant and almost-nightly live jazz in the bar, that it was used as the setting for several of the rendezvous in E.L. James’ infamous Fifty Shades of Grey—although, for most guests, the original crystal chandeliers and marble fireplaces inspire magic enough.

Housed in a 100-meter-tall, concave building in the heart of Xintiandi, the 24-story property has rooms with enduring views over the neighborhood’s Shikumen storefronts. Accommodations combine dark woods, floor-to-ceiling windows, green and gold wool carpets with a paisley-like motif, and dual-basin bathrooms with oversized bathtubs. Shanghai’s Art Deco period and Xintiandi’s courtyard houses inspire interiors, while color schemes of black and green appear throughout, from the dark local granite used as flooring and walls to green glass detailing. Another recurrent theme is the horse, a key Han symbol, laser-cut into large lobby columns and bronze beams to resemble bark on a tree.

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.

Hemingway’s Restaurant has the best sunset views of one of the world’s most beautiful beaches, Grace Bay, from a pier-like patio. The restaurant at the Sands at Grace Bay Hotel makes blended-just-right Pina Coladas topped with an extra dollop of rum. Sip and keep watch for the resident dolphin JoJo, who has been patrolling the turquoise waters off this picture-perfect crescent of sand for more than a decade – there’s even a bell to ring if you see him, although who knows if it’s the same dolphin. After you get tipsy, order dinner. In addition to conch, the restaurant is known for steak and fresh-caught fish cooked only in olive oil. At lunch, the fish tacos are my favorite dish. There is live music twice a week.

Take in the atmosphere of Helsingborg’s medieval tower, which doubles as the best photo opportunity in the city. You’re made to work for it though, as you’ll have to walk across gravel paths and climb a steep wooden staircase to reach the top of the tower. Built during the early 14th century, the keep was formerly part of a much larger castle that played a key role in Swedish-Danish relations over the centuries. Find out more at the new exhibition that focuses on medieval life during the tower’s heyday.

When Philadelphia‘s battered asphalt and noise begin to tire, head for an afternoon at Longwood Gardens, a verdant hamlet 35 miles West of the city in the Brandywine Valley. 1,077 acres of horticultural magnificence occupy one of Pierre S. du Pont’s many estates, including an impressive conservatory that stretches about 1/2mile. Ornamental gardens and topiaries, which rotate regularly, can be appreciated all year round in addition to seasonal illuminations (the Christmas light display is so well-received, guests must reserve tickets in advance). It’s not only the sheer size of the property that draws in visitors from around the world but the robust display that easily rivals the impeccably manicured gardens of Europe. The indoor children’s garden, treehouses, model trains (seasonal) and concert series make Longwood a great option for traveling families.

For something beautiful, unique and quintessentially Chinese, you’ll want to pick up a yak-wool knit from Shokay. This incredible social enterprise works with yak farmers in Western China to teach them how to harvest the finest down from their yaks. From here the wool is sent to a group of trained spinners who work their magic, turning the down into the most luxurious, soft yarn. Further transformed into elegant wraps, scarves, jewelry, hats, mittens, throws and pillows, Shokay’s collection offers perfect locally-made, ethically-sourced, beautiful gifts to take home. Store Location: InShop, 1605 West Nanjing Road (Just above JingAn Temple Metro Station, Line 7/Gate 10). Tucked back on aisle “D”, you’ll find Shokay’s pieces in an open space boasting a collection of Shanghai-based designers and labels. And for a true adventure, SHOKAY has transformed its knitting cooperative on Chongming Island into an open textiles workshop. Just over an hour away from Shanghai, the creative space welcomes visitors to spend the afternoon relaxing, joining in knitting classes, or custom ordering hand knit pieces from yak down. For more information, visit their website.

Swimming and snorkeling around Xtabi (pronounced “X-tah-bee”) Resort’s underwater caves are a unique experience and a well-kept secret from first-timers. While it’s a great place to stay, overshadowed by places like Rockhouse Hotel, you don’t have to be a guest to enjoy this “meeting place of the Gods” as the name describes. You’ll want to have lunch at the casual, outdoor restaurant first--choices are excellent and include club sandwiches to jerk chicken (even if a tad pricier than from the street grills). After lunch and a rest, change into your swimwear and make your way carefully down the steps until you reach a sandy cove entrance into the sea, beside caves and jutting rocks. Splash in and come out on the front side of the cliffs, where there are ladders to exit or enter as well, if you’re feeling a bit timid. A laid back environment, gorgeous waters--just a tad more jade-colored on this end, for some reason--and underground caves ideal for photo ops make Xtabi a great spot to spend the afternoon. When you tire, climb back up to sip on a Dirty Banana and sunbathe on one of the platforms beside splashing waves.

Much more than just a restaurant or smoothie stop, Choice Health Bar is a culinary fusion of food, lifestyle, and positivity. This small restaurant in the Lahaina industrial park serves fresh kale salads and heaping acai bowls. The place is a favorite hangout for island locals from surfers and paddlers to vegans. Just because it’s healthy, don’t think the food will taste like cardboard. Creative concoctions pepper a menu that is constantly being reinvented, and you’d never expect that a quinoa quiche could possibly taste so good. Locals also love Choice for the laid-back atmosphere and powerful, positive vibes. A sign on the door informs all patrons that this is officially a “bummer free zone,” and instead of simply “super-sizing” your meal, you can “make it epic” with ‘superfoods’ like kale and cacao. Consistently voted as the island’s top pick for healthy, vegan cuisine, Choice is the absolute best spot on the West Side for infusing your body with nutrients.

Atenas (whose name means Athens, as in Greece‘s capitol) is actually a quaint agricultural town in the province of Alajuela, about a 45 minute drive west of San Jose. With a population of only 27,000 people, and surrounded by coffee plantations and mountains, this is the absolute perfect place to experience Costa Rica as it truly is. The village has cute shops, some eateries, and stores that will carry any items you may need during your stay. The town square is adorable, and the various restaurants (all very casual) have excellent food based on local fresh catches and fresh-from-the-farm fruits and vegetables. The particular view above is from a lookout point on a private gated property. However, there are three housing developments in the area, and various owners rent out their places for very reasonable rates, and plenty have a view like this. Another fast fact about Atenas: it’s claimed to have one of the best climates in the world according to National Geographic, and you will come to know the phrase ‘El Mejor Clima del Mundo’ because it is proclaimed everywhere - and it’s true.

A beautiful drive through the mountainous west coast past the bayside city of Mayaguez opens up to windy roads lined with banana trees. Your destination is the coffee town of Maricao—a small, unassuming city that plays host to festivals, coffee tours, and aquaculture. Also the home to the hidden gem of Salto Curet waterfall. To get down to your starting point, a car with 4x4 is preferred but not always necessary (Going during the rainy season? Drive a truck or SUV). You’ll park in a vacant lot at the bottom of a hill and follow the trail over a river and up the mountain. You’ll eventually reach an abandoned ranger station; at that point you’ll turn left and trek up river. Just a short distance later is the isolated waterfall. Take a swim in the cool water, or hunt down the even smaller trail off to the left that takes you up the rocks to the higher and more roaring waterfall above. This is my most loved waterfall site. It’s secluded and never sees many guests at one time. Bring your camera and a waterproof bag, as it’s likely you will be caught in the rain. It is a rainforest, after all!

Come here and you’ll find a solar-powered bookstore, a Guatemalan restaurant, pubs, galleries, cafés, and this brick wall tribute to Gregory Colbert’s “Boy Reading to Elephant.” (The words that come to mind when I pass this street art are “tell me a good story and I’ll never forget.”) Just a few blocks north of downtown, and a few blocks west of the University of Arizona, Tucson’s Fourth Avenue district is a pedestrian eat-work-drink-play neighborhood with a new streetcar/trolley system. Construction is done, shops and restaurants are open, and you’ll find hardly a chain along the eclectic streetscape. From college kids and downtown workers, to artists, professors, and out-of-towners, Fourth Avenue is where the Old Pueblo welcomes techies and yuppies along with the ex-hippies... And, every winter and spring, for decades now, the neighborhood hosts a Street Fair—hundreds of thousands of people come for the arts, crafts, food, and music.

The Rosedeer Hotel is one of the first buildings you see in Wayne, sitting squat on a narrow piece of land between the railroad tracks and the hills behind. It looks like a movie set, and has been. Running Brave, Shanghai Noon, and In Cold Blood were shot here along with numerous commercials and music videos. A ten-gallon hat riddled with bullet holes wouldn’t look out of place. Don’t expect fancy cuisine—burgers are the norm, and if you want a steak, you’ll be delivered the meat and instructions on how to use the BBQ out back. But people don’t come for the food. Wayne is an authentic Western outpost, built before the road and at one time a thriving town, thanks to the nearby Rosedeer Coal Mine. People come in now for photo ops, for a chance to see one of the few remaining holdouts of the Wild West, and because the 100-year-old hotel and adjacent saloon are said to be haunted. But owner Fred Dayman, who was born and raised in the hotel, won’t talk about it. Book a room, if you dare, and find out for yourself.