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The multi-tiered wooden decks and cozy thatch-roof rooms, combined with the lush green hillside setting, makes Monkey Valley feel like an island treehouse escape. At the foothills of Chapman’s Peak and rising above Noordhoek Beach, this hotel and restaurant is a secluded spot to have a sundowner among locals. The rustic charm of the hotel combined with the hearty meals served at Thorfynns will make you feel like you’ve escaped to a fairytale world - yet you’re still a mere 40 minutes from Cape Town.

Not all the fun happens below the sea here. For fun atop the water, head to Lac Bay, the largest bay in the ABC Islands (Aruba, Bonaire and Curaçao, for the uninitiated). Kayaking through the resident mangroves, you’ll see all manner of birds and fish—particularly if you rent a glass-bottomed kayak. Meanwhile, the combination of consistent trade winds and sheltered shallows makes for some of the world’s best windsurfing—even if you’re new to the sport.

Having trained in Germany at the Goldsmithing School Pforzheim, Balaclava Jewellers proprietor Philip Cadien curates a collection with a refined, distinctly European feel. From precious metals, to exquisitely cut stones, to South Sea pearls, a visit is a feast for the eyes.

Chef Patrick O’Connell opened his country restaurant out of a former gas station in 1978 and rave word-of-mouth reviews soon made it “destination dining.” He opened rooms in 1984 and a few years later, it became a member of the prestigious Relais & Chateau hotel association. Today, it remains one of a handful of country hotels worth the trip for the meal as well as the stay, and it continues to rack up stars and top lists for dining and accommodations.

Two dozen opulent rooms reflect the style of a whimsical English country manor (as interpreted by O’Connell and London stage designer Joyce Conwy Evans), setting the tone for an over-the-top dinner with an exacting attention to detail. Be sure to visit the kitchen after your meal to see culinary magic in action. Little Washington (the first town named by George himself) is a bit over an hour from its capital namesake, and the Inn’s campus of guest rooms, shops, and gardens are spread over the colonial town; take the Perimeter Path walk to visit all of the farm operations and the newest guest quarters: a Little Bug Inn for pollinating and beneficial insects.

There is a sliver of Africa where four countries almost converge: Zambia, Zimbabwe, Namibia and Botswana. The Chobe River is one of the many separation points between Botswana and Namibia and it’s also where I experienced one of my favorite wildlife adventures of all time. The boat I called home for a few days is permanently moored in the middle of a vast river system of wetlands and river grasses. The marshland is rich in wildlife; hippos, birds of all kinds, Cape Buffalo and hundreds of elephants converge on this one spot. The elephants were perhaps the most impressive, in size as well as sheer numbers. While boating along the river one day the driver shushed us, cut the engine and pointed to the riverbank. There on the shore were two young elephants walking with great purpose towards the water. I had never thought about whether or not elephants could swim , but I soon got my answer. They plunged into the river without fear and began to swim with zeal and power to the coveted river island. They also didn’t seem to care about us as they came within a few feet of our boat. Watching these majestic animals ford the river and then emerge with a great splash was extraordinary. It’s one of the travel moments that makes you feel both alive and incredibly thankful.

This Upper East Side legend opened its doors in 1930 and, since then, has offered big-city accommodations to a legion of luminaries, from John F. Kennedy and Ingrid Bergman to the Duke and Duchess of Cambridge. The hotel’s famed restaurant Café Carlyle is where much of the action—and longstanding history—exists, having consistently hosted top talent like Woody Allen, Alan Cumming, and Rita Wilson since opening in 1955.

Come for a sip of the Cliff Bell at happy hour (that’s Dewar’s Scotch, sweet vermouth, Absinthe Ordinare, and orange bitters), stay for the live jazz and the lively 1930’s atmosphere. Cliff Bell’s jazz bar in downtown Detroit is a slinky watering hole, and a legendary one at that, named for speakeasy owner and colorful local entrepreneur John Clifford Bell. Although the club was shuttered for 20 years from 1985 to 2005, it now swings on with nightly live music and even serves up bottomless mimosas for Sunday brunch.

Put on your comfortable shoes and head to the many trails of Cayman Brac to see wildlife, as well as scenic and geological sights. There is a path for all skill sets. Listen to the mating calls of the parrots flying above at the National Trust Parrot Reserve Hiking Loop, or descend carefully into Peter’s Cave and move through the various layers to discover a truly breathtaking natural wonder. Most hotels have a brochure of all the hiking trails; this includes images, difficulty, and a brief description of each trail.

A warren of rooms make up this cozy restaurant that some claim is the oldest on the island. The building itself was originally a private waterside home constructed in 1652—some 40 years after the first English settlers arrived to Bermuda—and it has operated as restaurant for more than a century. The name comes from the married Irish poet who lived here and spent his days on Bermuda composing love poems to local women. However, don’t let the tavern in the name fool you: The cuisine and vibe here is haute, and the menu showcases French influences on island favorites, as well as traditional Bermuda fish chowder and grilled meats; if they’re listed on the day’s menu, the soufflés are a must-try. There’s no longer exactly a dress code (the emphasis is on “elegant casual”), but like everything in Bermuda, it is best to err on the side of formal.

Wymara Resort Turks & Caicos (formerly the Gansevoort aims to be as much a scene as it is a hotel. Of course, with tots wandering through the lobby with sand buckets, it isn’t quite the party you might have in South Beach or NYC. But then, trendy urbanites don’t have this—the white-sand beach of Grace Bay, or an infinity pool with wood-deck islands that can be reserved for sunbathing, private dining, or just making everyone else feel less important. The 91 rooms are designer chic, with an open floor plan and plenty of space to stretch out. Also available for booking are seven luxury oceanfront villas, located on an elevated hillside overlooking the bay and Turtle Tail. Each features four to five bedrooms as well as two private pools, expansive indoor-outdoor living areas, sunken outdoor lounge areas with firepits, and over-the-water swimming platforms with direct ocean access. Stelle, the Mediterranean-influenced restaurant, has a DJ who spins on Friday nights. And Exhale Spa counterbalances the chill party vibe with sunset yoga in an outdoor pavilion.

Within an hour, travelers can transport themselves from the lights and sounds of Central, Hong Kong, to the green hills and deserted beaches of Lantau Island. Opened in 2012, the Tai O Heritage Hotel encourages guests to immerse themselves in the natural beauty and history of Tai O, a colorful fishing village where stilted houses line the waterways of western Lantau Island. A collaboration between the government and the Hong Kong Heritage Conservation Foundation, Tai O Heritage Hotel was built in the former Tai O marine police station, from which officers defended Hong Kong from pirates for more than 100 years. Three buildings were transformed into nine guest rooms, an interpretation center, and a glass-roofed restaurant, earning the project a UNESCO award for cultural heritage conservation. Historic features such as cannons, guard towers, searchlights, and holding cells, as well as original architectural details like French windows, Victorian granite steps, a Chinese-tiled roof, and century-old fireplaces, were all restored in the process. The hotel also serves regional foods, employs villagers, and gives back to the Tai O community, demonstrating its commitment to celebrating the local culture. Beyond the historic walls of the hotel is a mystical landscape with dozens of butterfly species, Chinese white dolphins, and Hong Kong’s best sunsets.

Descended from horses brought over in the 16th century by Spanish conquistadors, hundreds of wild horses rule the little island of Vieques. The horses, an attraction in their own right, dot the landscape wherever you go. With every encounter, I couldn’t help but slow down and admire their beauty. They are naturally intelligent and curious, so don’t be surprised if they approach you or your vehicle looking for little treats. For a guaranteed encounter, look no further than Sun Bay—where I snapped this picture. Here, they graze, take frequent sand baths, and (if you’re lucky) cool their hooves in the blue waters of the Caribbean.

Few local D.C. residents know about St. Matthews Cathedral, and I would really be surprised if any visitors to D.C. knew about it, since it’s the National Cathedral that gets the mention in the guidebooks. That’s too bad, really, because this tiny Catholic church, with its unassuming exterior, has a glorious interior that few people see and appreciate. (Believe it or not, I get to come here for my Spanish classes.) Although it is a neighborhood church, it’s had its moments in the national spotlight. There have been many funeral services held here for notable people, including President Kennedy. For a cathedral, it has a very small interior—there are only seven chapels. The walls and ceiling are decorated with stunning images of angels and saints, including Matthew, rendered in marble and mosaic. The center dome helps to make the space feel larger. Last, but not least, there is a beautiful organ that is often featured in concerts and recitals; the sound of the music that pours forth from it is amazing! If you are visiting from out of town, I would recommend going to the church in the late morning. Then walk back toward the White House, stopping for lunch in McPherson Square. That’s where some of D.C.’s fleet of food trucks parks every day. Find a spot in the park to eat and enjoy your time in D.C.! The church is located about five blocks north of the White House and is a short walk from the Farragut North Metro station.

This five-star beachfront hotel toes the line between being a hub of activity and a luxurious, only-in-Southern-California hideaway. For restoration, head to the sprawling spa for a customized wellness-oriented treatment or a meditation class. Mind cleared, make your way to the on-site outfitter Compass Sports—where staff will coordinate local mountain biking, paddleboarding, hiking, and surfing expeditions—or to the palm tree–lined, mosaic-tiled pool. Big ocean views and a light, airy design define the 250 rooms; for guests seeking extra solitude and space, there are bungalow suites, which are essentially private beach houses. At the hotel’s three eateries, it’s all seasonal all the time, from the fresh morning juices to evening cocktails. That ethos peaks at the fine-dining restaurant Studio, where executive chef Craig Strong creates elegantly plated French-meets-California dishes using locally sourced fish and meat, along with vegetables picked from the hotel’s 1,000-square-foot garden. Pro tip: In a setting this transporting, you almost want to break into song. Good news—the hotel will rent out mini guitars to guests for the duration of their stay.

Guidebooks often lack the practical pieces of advice that could save travelers some rather unpleasant moments, in the Greek Islands one such nugget of wisdom I missed in my reading was that after a late night fueled by Ouzo it is not ideal to ride in a high speed ferry. Thankfully the ferry ride from Mykonos to Naxos is a short one at under an hour. I was greeted at the terminal by part of the family that runs Hotel Grotto, a small retreat perched on the edge of the Aegean sea that would be my home while in Naxos. After weeks competing for beach chairs and being corralled down tight marble alleys in some of the more frequented islands, Hora (also known as Naxos Town) proved the perfect place to relax and experience Greece at a slower pace. Upon arriving to the hotel, the bags were taken out of my hand and replaced with a glass of wine made by “Pappa” along with local olives as I was led out to the pictured patio. The view from patio of the hotel is of the Portara, believed to be the beginning of the Temple of Apollo dated back to 530 BC and is an ideal spot to pack a picnic from the local grocery, and watch the sunset before heading into town for the night. On the walk back to the hotel rising above the town is The Venetian Castle Kastro. During the day it serves as a museum offering tours, on Sunday nights after sunset it hosts traditional music and dance made easier by the accompaniment of Kitron,a liqueur indigineous to the area.