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There aren’t too many opportunities in the Caribbean to ride on horseback to a cave. In Los Haitises National Park, located three hours west of the resorts of Punta Cana, Fun Fun (pronounced “Foon Foon”) Cave is officially known as the largest cave in the Caribbean. Though the cave itself is in the National Park, access to the land goes across a private ranch and requires a guided tour. While the nearly three-hour drive from the resorts of Punta Cana is a lengthy, bumpy, journey into the interior, the scenes from the window provide an authentic glimpse into rural Dominican life. Sugar cane sways, schoolchildren wave, and mangoes drip from the trees. Upon reaching the ranch where you begin the tour you are shimmied into a jumpsuit and saddled onto your horse. A 45-minute ride through the shaded forest brings you to the edge of the National Park. From here it’s another 30 minute walk through sun-swallowing trees until you reach the entrance of Fun Fun Cave. Sliding into a harness and climbing gear, entering the cave requires a 50 ft. repel into a tiny hole which can barely fit your shoulders. Once at the bottom, it’s a one hour slog through the depths of the darkness before reaching the other exit. Inside the cave, stalactites and stalagmites pepper the areas which fall in the beam of your flashlight, and at some areas you are forced to swim through the soothing, subterranean waters. Here, a lone rope helps guide visitors through the hidden recesses of the cave.

At-home entertainers will enjoy the expansive digs at this Upper West Side property, where a number of studios and suites feature terraces and enough space to host upwards of 30 guests. Even its more modestly sized rooms evoke big-time comfort, though, thanks to luxury bedding, signature mattresses, and an array of everyday conveniences (think Keurig machines and free morning papers). There are plenty of perks to be found beyond the rooms as well, namely at the property’s three dining venues. Serafina restaurant excels at Northern Italian plates, while LOCL offers speakeasy-inspired cocktails alongside live piano sets and a library with an original fireplace. Guests will also want to check out RedFarm, where chef Joe Ng serves clever takes on Chinese fare and dim sum, such as oxtail dumplings and BBQ duck lettuce wraps.

It takes patience and good fortune to create a unique image in a place considered Canada’s second-most-photographed landscape. The Through the Lens Cruise on Maligne Lake gives amateur and professional shutterbugs such an opportunity. While in the boat, the onboard instructor talks technique and composition with aspiring photographers and challenges seasoned veterans to try new perspectives. Once the group arrives at Spirit Island, everyone spends an hour framing the perfect shot. The cruise experience hasn’t changed much since Jasper National Park pioneers Curly Philips and Fred Brewster set up shop at Maligne Lake in the 1920s.

One of the newer boutique inns to emerge in the Catskills, this 11-room property is a gorgeous mix of old-fashioned elegance and urban styling. Guests can expect classic features such as stone fireplaces and sheepskin rugs along with a glorious hodgepodge of vintage sofas, Moroccan tiling, and framed butterflies. Rooms feature white walls and matching linens, with pops of color in the form of grass-green rugs, tufted velvet chairs, bright wallpaper, and serene, forest-inspired art prints. Just be aware that about half the rooms—specifically, those on the third floor of the old house—share common bathrooms. There’s also a cottage with three bedrooms and its own kitchen, where guests can bring their pets provided they let the owners know ahead of time. Don’t miss the Sunday brunch served in the intimate Bar Room—one of the inn’s owners is a chef by profession, and his culinary artistry gets consistently rave reviews.

Just 30 minutes from the bustling tourist towns of Gatlinburg and Pigeon Forge sits this secluded bed-and-breakfast surrounded by 200 forested acres. Accommodations at Christopher Place are intended for couples rather than families: Nine individually decorated rooms, four with in-room hot tubs for two and several with fireplaces, have only one bed, and children younger than 12 aren’t allowed.

You can savor in-room breakfasts and dinners in a few of the rooms; everyone else can enjoy meals at the Mountain View Restaurant, which serves an affordable, seasonal four-course menu with a backdrop that’s just as satisfying. Hearty breakfasts will gird you for a full day of exploring Great Smoky Mountains National Park, or just hiking the trails outside the resort’s front door. Return for a dip in the pool, then a cocktail or glass of wine in front of a roaring fire at Marston’s Library Pub, named after the property’s owner.

You’ll feel zen from the moment you drive in from nearby Kyoto, along a narrow road through Japanese cedars and past temples and shrines, to the moment you sink into a hot bath at this intimate ryokan. Refreshed and relaxed, you’ll then sit down to an exquisite kaiseki meal of freshly foraged food prepared by a Michelin-starred chef. Oversized windows bring the outdoors in to the immaculate and simple tatami rooms, which come with both lunch and dinner. Book well in advance, given the inn’s small size and low-tech reservation system.

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).