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  • 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.
  • 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.
  • 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.
  • 163 Chico Rd, Pray, MT 59065, USA
    With only a couple of exceptions, you can’t soak in Yellowstone’s thermal features (this is for numerous reasons, not the least of which is that most are so scalding hot they’d burn the flesh off you). North of Gardiner, Montana, though, in the no-stoplight community of Pray, Chico Hot Springs has welcomed soakers to its spring-fed hot pools since 1900. Spend the night in one of the quirky rooms in the historic main lodge, originally built as a boardinghouse for miners, or in a refurbished caboose from the Northern Pacific Railroad. If at all possible, plan to be at Chico on a Sunday morning, when it serves the best brunch in Montana.

    When the Art family bought the struggling Chico Hot Springs Resort in 1972, some of the earliest improvements they made were to its dining room. The idea was to create one of the best restaurants in the state; if guests came for the food, maybe they’d spend the night. The family succeeded. Today the Chico Dining Room is so beloved it spawned a cookbook, A Montana Table: Recipes from Chico Hot Springs Resort. While ingredients are as fresh as can be—with produce from on-site greenhouses, meat from local ranchers, seafood flown in overnight from the coast—the menu includes some dishes that have been around for more than 40 years. The classic Chico meal is beef Wellington (service for two) and, for dessert, a Flaming Orange, which is exactly what it sounds like.
  • Gibbs Cay, TKCA 1ZZ, Turks and Caicos Islands
    Swim with large southern stingrays in the warm blue water around Gibbs Cay. This secluded seven-acre island is a short boat ride from Grand Turk and a popular day trip for many visitors. The stingrays are quite friendly after years of regular feeding and interactions with humans. Your boat guide will provide fish scraps to feed the rays as you snorkel in the shallow water. Day trips may also include time on the island and stops to snorkel and dive for conch.
  • 2117 Whistler Rd, Whistler, BC V0N 1B2, Canada
    Rimrock Cafe stood by itself as Whistler’s destination dining room for years as Whistler Creekside Village matured around it. Chef Rolf Gunther’s menu doesn’t dazzle you with fads, but focuses instead on classics such as terrine of duck confit, foie gras, rack of lamb, and the Rimrock mixed grill, featuring filet mignon, lamb chop, and venison. Like the menu, Rimrock’s cocktails recall former days when every element of a dining experience was done exactly right (try the Canadian Whisky Sour). Not surprisingly with its cuisine and cocktails held at such high standards, Rimrock is known for consistently impeccable service.
  • Camping
    Tofino, BC V0R 2Z0, Canada
    In a remote spot off Vancouver Island in British Columbia, surrounded by rain forest, mountains, and beaches, the Clayoquot Wilderness Retreat first opened in 1998 as an overnight floating lodge experience; since then, it has grown into a luxury tent retreat. While the camp has a rugged outpost atmosphere, with huge stone fireplaces and a long wooden cookhouse, it’s an outpost with every possible luxury: from white linen tablecloths and polished silverware to soft comforters and high-thread-count bedding.
  • 1 N Kaniku Dr, Waimea, HI 96743, USA
    In many ways, the Fairmont Orchid is the quintessential Hawaiian luxury resort. Its big, elegant lobby is blooming with purple orchids and birds of paradise, its enormous, 24-hour swimming pool wends its way around black rock islands, and its 32 lush acres include tropical gardens and a white-sand beach that frames an aquamarine cove. The 540 guest rooms and suites, located in two six-story towers, all have lanais; half have ocean (or partial water) views, the others overlook the spotless grounds. It’s the dream Vacationland, and as such, the mood is jolly round-the-clock. Cheerful staff oversee the long list of activities—canoe excursions, petroglyph hikes, stand-up paddle-boarding, and about a zillion other options are available both on property and off (some activities are complimentary, others cost extra)—and the crowd tends to be a fun-in-the-sun bunch. On any given day, there might be a Canadian family in a heated volleyball game on the beach, or a group of Silicon Valley execs soaking in the hot tub.

    Carve out a day to spend at the award-winning Spa Without Walls, where the Hawaian-influenced treatments are performed in 17 treatments rooms, some with ocean views and private outdoor spaces. Them, fuel up on Japanese meats and sushi, fresh seafood, robatayaki (grilled) items, beachside classics, and more at the numerous dining outlets. Along with repeat guests, the hotel’s most frequent visitors are the giant sea turtles that regularly hang out at the Orchid’s beachfront. They’ve become such an integral part of the property that even guests at other hotels drop by for a peek.
  • San Fuego 70, Santa Cruz, Aruba
    Among the 20 percent of Aruba that’s protected land, Arikok National Park boasts lava fields, limestone terrain, and a small beach, all crisscrossed with picturesque hiking trails. Paths lead to gold mine ruins, former plantations, and paintings by the island’s native Arawak people, making for an exciting place to visit. Explore the park by mountain bike, horseback, or car, or take a free walking tour with a park ranger (reservations must be made at least 24 hours in advance). You’re likely to see snakes, owls, bats, lizards, and myriad birds, as well as goats and the local donkeys.
  • Kehlsteinhaus, 83471 Berchtesgaden, Germany
    Adolf Hitler’s mountain retreat, the Eagle’s Nest combines haunting history with stunning panoramic views. Located high in the Bavarian Alps, this famous Third Reich construction was bought for the former German Führer as a 50th-birthday present. Today, the spot (also known as Kehlsteinhaus) is open to the public. After a bus journey to the base of the Eagle’s Nest, visitors walk through a long tunnel and make a final 406-foot ascent in an elevator embedded into the mountainside. Once inside the building, don’t miss the Italian marble fireplace—a present from Benito Mussolini. Also note that weather conditions may cause the Eagle’s Nest to close at certain times of year, so summer is your best bet to visit.
  • 301 Front St W, Toronto, ON M5V 2T6, Canada
    Since it was built back in 1976, the CN Tower has topped the must-visit list of most Toronto tourists. Until recently, a visit was pretty standard; hop in elevator, shoot up to the observation deck, and ogle the city from a hawk’s vantage point. While this was certainly fine and enjoyable, the since-developed EdgeWalk experience has ramped up the Tower’s bucket-list potential. Thrill-seekers can now do a hands-free, breezy circumnavigation of the tower’s roof, up at 1,168 feet. And, yes, they do perform sky-high weddings complete with elasticized rings and special attire for the big day.
  • Oljato-Monument Valley, UT 84536, USA
    Nuzzled up against the Arizona border about 100 miles west of Four Corners are some 30 square miles of the most iconic scenery in the American West. Monument Valley is one of those places that you’ll recognize as soon as you see it, even if you’ve never been there before, as dozens of movies, TV shows, and even video games have used the area as a setting. It’s made up of mesas both small and large reaching up from the valley floor, some rising as high as 1,000 feet into the sky. Part of the Navajo Reservation, the area charges a $20-per-vehicle entrance fee to drive the dirt-road loop. Once in, however, you can also enjoy a number of hikes, or hire a guide for a horseback tour.
  • Passage Prince Moulay Rachid
    Described by writer Tahir Shah as the “greatest show on Earth,” no visit to Marrakech would be complete without a visit to the famous night market on the Djemaa el Fna. Arrive before sunset and park yourself at one of the various cafés with terraces overlooking the square to watch performers set up; then venture into the fray in search of adventure. Silk-clad acrobats, wide-eyed storytellers, sly snake charmers, jangling belly dancers, and capricious monkey handlers all emerge from the darkness, ringing the edge of the food stalls with their own special brand of entertainment. When you tire of the heckling, prowl the market in search of good things to eat: bite-size morsels of grilled lamb rubbed in cumin, sardines fried in chermoula, peppery snails, and sheep’s heads for the brave. Then nudge up alongside a family of locals at the table and settle in for the feast. If you’re nervous about going it alone, you can sign up for a food tour with Canadian tour guide and all-round good egg Mandy Sinclair of Tasting Marrakech; she’ll help you find the best stalls while introducing you to the secrets and delights of traditional Moroccan street food.
  • Negril, Jamaica
    No hotel in Jamaica blends better with its surroundings than the aptly named Rockhouse, a string of villas clinging to the top of a sea cliff at the western tip of the island. Local stone, timber, and thatch are the building materials, and a harmony of design and setting is the result. The feel is rustic, but not rough (the showers might be outdoors, but the rooms are air-conditioned), and the feeling carries over to the pool, which sits on a rock platform halfway down the cliff face, from where sunbathers can don snorkel and mask and clamber down into a usually calm Caribbean. Even the restaurant hangs over the water, adding emphasis to the promise of dishes being fresh from the sea.

    As does practically every hotel in Jamaica, Rockhouse has its celebrity stories, going back to the early ‘70s when Bob Marley, Bob Dylan, and the Rolling Stones added their names to the guest register. But it wasn’t until 1994, when a group of Australian owners took over, that Rockhouse began to evolve its reputation as one of the most Jamaican of Jamaican hotels. It happened in part because Rockhouse has none of the formality that some of the island’s best-known hotels, with their British colonial roots, still possess. And in part because of its active role in funding local education projects, it’s a valued, and popular, part of the community. That, and the restaurant’s homemade jerk sausage is legendary.
  • Kleintuin Rd, Simon's Town, Cape Town, 7995, South Africa
    There’s a different way to see the African wildlife in their natural habitat than a safari and it’s called Boulder Beach. We ventured to the Eastern side of the Peninsula (Indian Ocean) to meet and spend time with the locals, Cape Town‘s penguin colony. Following the wooden boardwalks, you gain access to Foxy Beach, a sheltered cove with soft white sand, crystal clear water, massive granite boulders, and birds in butler-style tailcoats. Its nothing short of an Instagram-worthy photo op but I recommend climbing atop a boulder and spending time to take it all in. It’s impossible to capture how majestic this destination truly is.