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This funky boutique hotel on the edge of the Britomart shopping district goes way back in Auckland history. Built in 1841 as The Commercial Hotel, the DeBrett building survived two fires and two rebuilds plus a stint as a hostel before becoming the quirky place guests experience today. The Housebar has always been the center of hotel life, and today, the intimate wood-and-mint venue exudes its original art deco style and serves classic cocktails and local beers and wines alongside refined pub snacks.

In addition to restoring the bar and adding a glass-roofed atrium that houses the hotel restaurant, DeBretts Kitchen, the current owners affixed contemporary artwork and photography throughout and sheathed the entire building in candy-striped carpeting, custom designed from 100 percent New Zealand wool. Besides the carpet and small-batch minibar selections, no two rooms are the same. Each features unique furnishings from the 1930s on, and every bed has an original screenprinted throw. Two of Hotel DeBretts centerpieces, the chandelier and water sculpture in the restaurant, were crafted by Auckland artists from materials salvaged during the latest renovation. The result is a local experience from top to bottom that gives guests a real taste of New Zealand.

At this luxury property perched over Matauri Bay near the top of the North Island, the colonial-style buildings are dwarfed by the endless wavy greens of a championship, par-72 golf course that ends at the Pacific. The ocean views and holes positioned adjacent to plunging precipices make Kauri Cliffs one of the most famous golf resorts in the world. The hilltop infinity pool is another crowd-pleaser, especially when it reflects the pinks and purples of the sunset. Featuring a beach-meets-country vibe, lodge interiors are outfitted with New Zealand artwork and furnishings imported from Europe and Australia. Outdoors, patches of totara trees dot the 6,000-acre property—one section houses the tranquil spa. Walking paths lead to a waterfall, three secret beaches, and picnic sites that offer sweeping views of Cape Brett and the Cavalli Islands.

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.

Rebecca Walker embarks on a spontaneous journey to Bulgaria, guided by locals she connected with both virtually and in real life.

The Caves, just west of Negril, is aptly named. While the 12 cottages and one villa sit atop honeycombed cliffs, the Blackwell Rum Bar, a private dining venue, and the massage table of the hotel’s Aveda Concept Spa are actually in underground grottos open to the sea. The setup is very Treasure Island, and the flicker of candlelight and the echo of waves off cave walls make it uniquely romantic. Each of the thatch-roofed cottages is as colorful as a paint box, and each gives a sense of being alone at the end of the land. This is one of music mogul Chris Blackwell’s Island Outpost properties, so the vibe at the Jacuzzi, sauna, or salt-water swimming pool is hip but relaxed. Although famed Seven Mile Beach begins almost where the cliffs end, the hotel itself has no beach, which is why a tradition at the Caves is to begin the day by jumping from the cliffs into the usually calm Caribbean below—or at least thinking about it.

Following a powerful earthquake in February 2011, the Christchurch Cathedral was severely damaged, and while there is an ongoing ideological and economic debate over whether or not the Gothic-style church can, or should be, repaired, the Anglican parishioners of New Zealand‘s second-largest city can now worship in this fascinating edifice made of, among other things, 96 giant cardboard tubes. Designed by Shigeru Ban, a Japanese architect who specializes in building temporary structures following natural disasters, the Cardboard Cathedral (formerly called Christchurch’s Transitional Cathedral), was erected in less than a year. Its excellent acoustics are also regularly utilized for concerts and events.

Perched just up the hill from the white sands of Oneroa Beach on Waiheke Island, the Boatshed fulfills the wainscoted, shuttered, pitch-roofed holiday images that dwell in the minds of beach lovers the world over. Originally the vacation cottages of designer David Scott, the Boatshed now offers six sun-drenched accommodations that complement the laid-back island vibe—a magnet for a free-spirited set of artists, vintners, chefs, and water lovers. Many furnishings were custom-designed by the Scott family and exude the feeling of a boat cabin, especially when placed among the built-in shelves and cabinetry of the bachs—the local word for an authentic New Zealand beach shack. Accommodations range from old boat sheds to a three-story tower that feels like a lighthouse, and outdoor decks provide many opportunities to enjoy the sea breeze. The boutique hotel was the realization of Daniel Scott’s dream—to share the simple pleasures of the beach life with travelers from around the globe.

In Greek mythology, Heracles slew all the sons of the King of Pylos except Nestor, who became king of Pylos himself. Nestor appears as a sage elder in both the Iliad and the Odyssey, expounding on how things were really tough back in his day. If you visit Voidokilia Beach, about 12 kilometers (7.5 miles) from Pylos, you can take a 15-minute walk to see Nestor’s Cave. First, enjoy your time on the beach, which is renowned for its natural beauty. Then climb over the dunes at the beach’s southwest end and follow the hillside path to the cave, which sits just below the ruins of the Paleo Kastro, the old Pylos castle. As legend has it, this cave is where Hermes hid the 50 cattle he stole from Apollo. The trip is worth it for the views alone: The higher you go, the more you’ll see, as the panorama takes in Voidokilia Bay, the Gialova lagoon, the Bay of Navarino, the Peloponnesian hills and the city of Pylos.

AFAR chose a destination at random—by literally spinning a globe—and sent Rolf Potts on a spontaneous journey to Russia.

Rising before one of the world’s most famous sailing sites—the host of the Louis Vuitton Regattas, the Volvo Round the World Race, and the Auckland International Boat Show—the Sofitel Auckland Viaduct Harbour blends French and South Pacific influences while respecting the maritime heritage of the area. Glass walls maximize views of the marina and its many yachts as well as the reflective pools that create optical illusions in the hotel lobby. The color palette sets cherry and dark woods, jade greens, and slate grays against cream and white backdrops, while artwork—from ceremonial pieces to a Maori tribal sculpture in the atrium—pays homage to indigenous New Zealanders. Some of the treatments at the SO Spa, like the greenstone massage, also reflect local culture, while others use French products in a nod to the hotel brand’s heritage.

References to Auckland’s volcanic origins also abound, most notably in the back-lit marble walls of the Lava Dining restaurant, an all-day spot for French- and New Zealand-accented dishes; the casual 21 Viaduct Café and panoramic Sabrage Bar are other dining options. And then there are the rooms: from the Superiors and Junior Suites to the exclusive Opera Suite, all have contemporary décor, signature MyBed mattresses, marble baths with Lanvin products and separate showers and tubs, and walls of windows opening out onto a Juliet balcony with views of either the hotel’s atrium, or the city, harbor, and beyond.

Bantayan Island’s fine white sand beaches and clear light blue waters are as enchanting as far busier Boracay, minus the noise and go go go night life. The island’s Ogtong Cave Resort offers a well-kept landscaped garden, a pool, and individual cottages, but the real draw is a cave below the resort grounds, where you can explore and wade in the waters. Rooms at the resort are simple and comfortable. The resort offers doubles up to family rooms with plenty of room for kids. There are two pools on the ground, with one reserved for resort guests. The usual jump off point is Cebu, a one-hour flight away from Metro Manila. You then take an almost 3-hour bus ride from North Terminal to Hagnaya for a 75-minute boat to Santa Fe, Bantayan. You can also opt to take a private van or taxi for a more comfortable and faster ride. Don’t be put off by the long travel time--the beach, cave, and everything else at the resort are well worth what it takes to get there.

There’s a reason Blue Cave Castle (affectionately dubbed “BCC” by return visitors) has a following. Designed in the shape of a castle, it’s impossible to miss this dominating blue structure on Negril’s cliff side. Tower rooms offer dramatic views 50 feet above the sea, and yet surprisingly, rates start at $50 night and go up to only $120 for a stunning 2-floor “penthouse” suite on the top floor. Blue Cave is one of the West End’s best-kept secrets. Going to sleep in a castle to the immediate sound of crashing waves is a unique experience. Even if you don’t get to stay here, be sure to stop by the on-site Hideaway Eatery, owned and run by Chef Teddy, for a delicious lobster dinner.

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.

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.