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For much of its history, the western edges of Manhattan neighborhoods like the West Village and Chelsea consisted of small manufacturing buildings and warehouses that served the piers on the Hudson River. Over time, those factories were replaced with residential developments, and shipping largely moved out to Brooklyn and New Jersey. What remained, however, was an abandoned light-rail line, located above street level. After 10 years of lobbying the city, state, and federal governments, the first section of the High Line park opened in 2009. It now extends for 1.45 miles, from Gansevoort Street in the south to 34th Street at its other end. An innovative design by James Corner Field Operations uses native species to preserve some of the feeling the old rail line had when it was overgrown with weeds. It has quickly become one of New York’s most popular attractions, both with residents and visitors who stroll the length of it, as well as a model for other cities attempting to find new uses for old infrastructure.

Nina Compton, a native of Saint Lucia in the Caribbean, came to New Orleans a few years ago to compete in the Top Chef television series. She didn’t win the culinary slugfest, but New Orleans came out ahead—a short time later she returned to set down roots by opening Compère Lapin, a charming, brick-accented restaurant in a hotel that’s a reasonable stroll from the French Quarter. It’s good to get there early to grab a drink at the bar, which treats its libations with the same seriousness as the kitchen does its food. (A frozen drink… with chartreuse.) The dishes are alive with creative Caribbean flavors—among the more memorable plates are the seafood pepper pot, black drum, and curried goat.

Reach Falls is an off-the-beaten-path delight. Located up in the John Crow Mountains on Jamaica’s east coast, this 30-foot jade-colored cascade tumbles into several pools in the surrounding rain forest. You’ll need a bathing suit and a waterproof camera to capture the natural splendor. Local guides are available to help you make your way across the swimming holes and levels, and show you the best spots. Or you can explore it solo. Because of its distance from tourism spots, there are no crowds, no harassment, just an entrance fee to your very own Garden of Eden. On-site changing rooms are available as you exit by the parking lot. Small fun fact: The falls play a minor role in the 1988 Tom Cruise movie Cocktail.

A marine sanctuary in northwest Maui, Honolua Bay delights snorkelers and surfers alike. The right side of the bay boasts dense, showstopping coral that attracts vibrant fish, while the shallower left-hand side features lava caves, archways, and sea turtles in the summer months. Come winter, some of Hawaii’s most beautiful barrel waves start peeling around the point, drawing only the most experienced daredevils. Note that fishing here is forbidden and parking can be tricky—visitors often have to park along the cliffs and hike down through a magical, Robinson Crusoe–type forest to the rocky shoreline. When approaching the bay, watch for mile marker 32. Just past it, you’ll find stairs down to Mokuleia Beach.

A trip up to the Dee Wright is a required trek for all my guests who visit Oregon. If you want to experience the power and beauty of the planet, the Old McKenzie Highway delivers an eyeful. Starting in Ponderosa Pine forests and climbing to 5,300 feet above sea level, the road wages a mighty battle to deliver travelers to the top. The structure at the pass is built out of lava from the surrounding flow and towers above the old wagon road that is now Route 242. The road is closed in winter, but it’s a busy corridor during the summer tourist season. The observatory has windows which become frames for the famous peaks easily seen across the barren landscape. On the top deck you can easily see Mt. Hood to the north on a clear day. An interpretive trail gives visitors a great geology lesson on Cascade volcanology. It is a very harsh environment with the blistering heat of summer and the raging snow storms of winter. One can hardly imagine moving though this moonscape in a covered, ox-drawn wagon back when Oregon was just a territory. Nothing like it.

Many Caribbean islands (Anguilla included) are made primarily of limestone. Over many thousands of years, caves often form in this type of rock speckling the islands with tons of little caves to explore. On Anguilla there are plenty to explore, but the hike to the Iguana Cave is particularly pleasant. It starts on the quiet and isolated sands of Katouche Bay Beach just past the Masara Resort. It’s pretty much due West of the capital of The Valley and very easy to find. The only awkward part is the very steep road that descends the last mile toward the shore. There you should find a gap in the sea grape trees. Staying on this path will take you past a salt pond, through a forest crawling with hermit crabs, up an old stone staircase, through a grove of cactus, past the occasional red-footed tortoise, and finally to the cave. Going at an easy pace, the hike clocks in at around 45 minutes up and 45 minutes back. For the most part, it’s pleasant and I highly recommend it as a way to break up a bounty of beautiful beach days.

A challenging dayhike with a glacial-lake view at the end, and then Bratwurst-und-Bier for dinner: a perfect summer’s day in Washington State’s central Cascades! Take Icicle Creek Road from the town of Leavenworth to Eight Mile Road, then turn left and follow it up to where it ends at the trailhead to Lakes Stuart and Colchuck. This is a forested granite peaks wonderland. The switchbacks are shaded and crisscross streams; waterfalls will replenish your canteen...At 5800' you arrive at Lake Colchuck, glacially-colored beneath Dragon Tail Peak and Aasgard Pass (The NW’s Nordic heritage is evident here.) You might be gasping for adjectives, but you’ll understand why this area is called “The Enchantments.” Back down in civilization, feed your post-9-mile-hike-appetite with hearty Teutonic fare; Leavenworth is a mining-town-cum-Bavarian-hamlet--faux, but well-done. The pseudo-German architecture hosts many eateries, including München Haus--with its outdoor Biergarten, it will welcome even sweaty hikers. Several kinds of Wurst are available, served with local microbrews. Slake your thirst and savor the scenery... (About 2 1/2 hours from Seattle.)

Vancouver’s serene waters serve as the perfect playground for kayakers and stand-up paddleboarders. Newbies can book two-hour “tasters” at Ecomarine’s Granville Island or Jericho Beach locations, while more adventurous paddlers—of any level—can jump right into tours, like the summer sunset excursion along the scenic shores of False Creek (a protected inlet) and English Bay (part of the Strait of Georgia). While most tours last a half or whole day, Ecomarine also offers more hard-core expeditions, like the weeklong trip to Haida Gwaii. This craggy, rain-forested archipelago is often referred to as Canada’s Galápagos for its vast number of endemic species. It also has a wealth of First Nations heritage sites just waiting to be explored.

The “new” Testaccio Market opened in a modern building next to the Ex-Mattatoio (former slaughterhouse) in the summer of 2012. The space was much larger than the original market, which meant there was plenty of room to grow new businesses, especially “fast food” stalls. While dining at the market is prevalent in many cities, Rome never had such a thing before Testaccio opened stalls like Mordi e Vai (meatball sandwiches).

Founder’s Note: Travel Like an American

The longest developed rail-trail in the country, Katy Trail State Park snakes across Missouri for 240 miles, from the western edge of the state to the St. Louis metro area. Built on the former corridor of the Missouri-Kansas-Texas Railroad, the well-maintained park closely follows the Missouri River, offering bikers, hikers, equestrians, and everyone in between a scenic way to see much of the state. The section between Cooper and St. Charles counties is an officially designated segment of the Lewis and Clark National Historic Trail, adding an educational aspect to any exploration. Most choose to bike a portion of the trail, though hiking, running, and horseback riding are also great ways to experience the park, all the while surrounded by forests, wetlands, prairies, and abundant wildlife. A favorite stop along the way is the charming town of Rocheport, where you can make a pit stop at the bluff-top Le Bourgeois Winery for fine wine and views of the Missouri River Valley.

Straddling a forested isthmus on Corfu, Kontokali Bay Resort & Spa avails its guests of five-star luxury while maintaining a fun, welcoming atmosphere for families. There are a wide range of accommodations (plus all-inclusive packages), from the 170 rooms in the main building to the 89 suites and bungalows clustered in lush gardens around the property; all have terraces or balconies, some with views of the bay or sea. For the VIP treatment, book the presidential suite, which features a private pool with two Jacuzzis, an indoor hammam, and a small gym. Beyond the rooms, guests have several choices for sunning and swimming, including two sandy beaches with loungers and umbrellas, a saltwater infinity pool overlooking the Ionian Sea, an indoor heated freshwater pool, and a kids’ pool in the playground area. Dining options are equally diverse: go casual at the beachside bistro, Mediterranean buffet, or taverna-style food court, or sample dishes that look as good as they taste at Asterias, the fine-dining restaurant.

The Blue Ridge Mountains stand in for the Black Forest at Grand Bohemian Asheville, a 104-room luxury property inspired by old-world Bavarian hunting lodges, complete with stag-antler chandeliers, rich velvet and brocade textiles, and a popular mascot in the lobby—a taxidermied wild boar named Zsa Zsa. In contrast to the more dramatic public spaces, rooms and suites are spacious and light with crisp white bedding and tufted headboards; almost all of the bathrooms have large tubs with shutters that open up to the sleeping area. In addition to the rare original artwork that’s scattered throughout the hotel, there’s a gallery featuring paintings, art glass, woodwork, and sculptures from local, regional, and international artists. George W. Vanderbilt’s Gilded Age castle is across the street, and the hotel is within walking distance of Biltmore Village’s popular restaurants and shops and only two miles from trendy downtown Asheville, making it a convenient jump-off for exploring the Great Smokies.

Interior designer and owner Denis Roy eschewed the palapa-inspired elegance employed by so many Costa Rican resorts in favor of a tropical take on European influences—Victorian architecture, French colonial touches, and Grecian columns among them—creating a resort like no other on the country’s west coast. Owing to its vantage point 1,100 feet above the entrance to the Gulf of Nicoya, the views of the rain forest, ocean, and sunsets are stunning, especially from the infinity pool. Rooms in the main building are fairly basic, but suites and villas offer more luxurious touches, such as Jacuzzis, private ocean-facing terraces, and plunge pools. The property has its own beach (with sun beds, showers, and a snack bar), but since it’s at the bottom of a steep hill, the resort provides hourly transfers. Retreat to the open-air yoga studio, then head to the bar atop the Greek amphitheater to linger over a martini at the nightly sunset happy hour.

With its pristine beaches, emerald lagoons, and wildlife-filled jungles, Manuel Antonio National Park is considered one of the world’s most beautiful natural wonders. There’s no better place from which to explore it than the five-star Arenas del Mar, an 11-acre hotel and reserve that’s set atop rain-forested cliffs overlooking the Pacific and delivers just the right amount of luxury within walking distance of the park. (Just don’t be surprised to cross paths with the occasional monkey, sloth, crab, or iguana.) The rooms on the upper level have ocean views and feature hot tubs on large terraces; beachfront rooms are a particularly good choice for families with children thanks to easy access to the lower pool and the casual Playitas Restaurant. But the resort is also an unexpected culinary beacon, serving sustainable dock-to-dish seafood caught by local fisherman that morning and certified gluten-free options alongside traditional Costa Rican specialties.