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Set on a steep hillside overlooking vineyards and the Silverado Trail, Stuppa Estate Napa Valley manages to be both secluded and well positioned for exploring Napa Valley’s wineries and towns. The suite-only property has five poet-themed rooms—refreshed in 2021 by Erin Martin Design and embellished with hand-painted murals by artist Michael Duté.

Each suite is themed after a literary icon, such as Emily Dickenson, and includes a private patio, a soaking tub, and an outdoor shower—including a few oriented toward the valley. Sunset is a highlight: All rooms face west, giving guests unobstructed evening views of the valley and vineyards below.

Breakfast is a lavish spread with dishes like seasonal pancakes or shakshuka—served either in-room or on the open-air patio. A small outdoor pool and on-site spa treatments add to the quiet atmosphere, and staff can arrange private tastings at Sullivan Rutherford Estate, a boutique winery under the same ownership. Service is a defining feature; the team handles everything from sunset cocktails to dinner reservations with a level of care that consistently elevates the stay.

I stumbled along this place on a recent trip completely by accident. We’d been driving aimlessly for a while west of Kardemena looking for the perfect quiet beach to take in the late afternoon when I spied a few umbrellas through the trees between the road and the shore. I was pretty much equidistant between town and some of the huge resorts further to the west, so I figured I’d found my spot! I pulled off the road, unpacked all my stuff, marched through the trees to the beach and was met with a decent little beach, a small bar, those umbrellas I’d spied from the road and a small collection of older couples... Completely nude older couples. I wasn’t expecting this, but hey, I had no interest in spinning on my heal and re-packing up the car, so I assumed the proper attire (none), spread a towel out on a beach chair and settled in. I’m a go-with-the-flow kind of guy, after all. The beach itself is a mix of sand, pebbles and some larger rocks. The water is immaculately clear. And, as it turns out, the whole spot is watched over by one person Mandy — perhaps the nicest British lady on Kos who greets beach goers with an inviting smile and incredibly pleasant accent. I may not have been looking to take it all off, but knocking back a few Mythos beers with Mandy made for a pleasant end to the day.

West Randolph Street in Chicago’s West Loop has become a new home to the city’s culinary talents. Stephanie Izard first drew crowds cooking dishes like roasted pig face at Girl & the Goat (the restaurant pictured above). She then opened Little Goat, a retro diner, across the street. Graham Elliot Bowles keeps it simple at his casual g.e.b, where each dish has no more than three ingredients. On a more elegant note, the prix-fixe menu at Grace, from chef Curtis Duffy, features dishes such as kampachi with coconut, lime, basil, golden trout roe, and pomelo presented in a cylinder of frozen ginger water.

Often called one of the world’s most beautiful beaches, Trunk Bay is a crescent of snow-white sand with a small green islet on the north side of the aquamarine lagoon. Part of the Virgin Islands National Park, Trunk Bay is known for its underwater snorkeling trail. Submerged signs along the trail describe the corals, tropical fish and other marine life found within the bay. Visitors can rent snorkeling gear on the beach, and lifeguards are in attendance.

Dining in a beach chair—or at least a chair by the beach—is an essential part of the experience at Spice Mill Restaurant, which looks directly across the water to St. Kitts’ sister island of Nevis. The menu here journeys across the global culinary landscape, but the fish and produce are sourced as locally as possible—including from the restaurant’s own gardens. Expect fine dining with your toes in the sand.

Check out the rocking, hip and popular Cowgirl, a melding of Texas BBQ and New Mexico flavors and Old West style. Early evening, there’s happy hour including cheap, tasty margaritas. At night, patrons kick up their heels to live music. There’s a big patio outside for plenty of sipping.

For pure private island bliss with a serious side of digital detox, I love hopping on the private boat charter and cutting through a sea of turquoise for 20 minutes to arrive at The Meridian Club on gorgeous, isolated Pine Cay. The only resort on the 800-acre private island, which also features 35 private homes but nothing else, has just 14 beachfront rooms and is luxe zen to the core.

The property has just 12 suites and two freestanding cottages and is the kind of place you come to digitally detox, to rewind and rejuvenate — there are no cars on this island and the most traffic you’ll see on the electric golf car is an iguana family crossing the road. There are also no televisions or telephones in the rooms although there is WiFi (but you are asked to not conduct phone conversations while here unless it’s an emergency as noise carries). The rooms are beyond spacious with a whitewashed beach vibe and large screen in porches with ocean views and direct beach access. I loved falling asleep to the sound of the ocean every night and the beds and linens were top notch comfortable. The suites also feature landscaped outdoor showers. The cottages are even larger with separate living and lounging spaces as well as having the screen-in porch and outdoor shower set up.

Beyond the rooms, I loved the staff at this property. Everyone was so friendly and went out of their way to cater to my every whim. The meals, which are included in the rate, are also quite good with a varied menu and beautiful presentation. The restaurant, known as The Bistro, is open to hotel guests and also the homeowners who live or vacation on the island, and on weekend nights post dinner it can take on a very fun vibe with dancing by the pool or cocktails in the second floor lounge space.

Staying here is definitely an isolated experience. It isn’t easy or cheap to access Provo for an afternoon, so it is best for couples or friends (it’s not very child focused) that are looking for a digital detox style getaway where you don’t need to be constantly connected (but there is still WiFi to Netflix and chill at night) or entertained by a myriad of restaurants, shops or bars. Here you get back to nature. Enjoy fresh, seasonal, well-prepared meals and stiff drinks at the bar and just soak up the island vibes in a beautiful private island atmosphere for a four or five nights. Afterwards, you can hit up Provo for a few more and it will feel like a big city adventure! Oh and it’s not like you will be sans activity. There is great snorkeling and diving on reefs just off Pine Cay and there are also opportunities for fishing, walking and yoga. Yep, when it comes to wellness getaways, The Meridian Club delivers.

The 2,000-acre preserve that surrounds this sprawling resort offers enough diversions to keep visitors occupied for weeks. Activity lovers can book a tee time at the Pete Dye-designed golf course, play a game on the hydro-cooled clay tennis courts, or tour the Spanish Water Bay by kayak or stand-up paddleboard. Miles of hiking and biking trails lead to expansive island views and hidden caves, and guides are available to point out local flora and help feed the island iguanas. The resort spa even offers weeklong holistic health and wellness retreats.

If you’re seeking a more low-key vacation, relax on the property’s 1,500-foot stretch of white-sand beach or enjoy a massage overlooking the sea. Restaurant options include open-air fine dining at Shore, Mediterranean dishes and themed buffets at Medi, and the poolside bar and grill Splash, all of which you can visit for daily meals with an all-inclusive package. The downside of the resort’s size is that its location can feel isolated, and guests need a vehicle to dine off-site or explore more of the island.

If you’re visiting Tahiti with a large family or group of friends and hoping to surf the island’s most powerful wave, you’d be hard-pressed to find a better, more affordable place to stay than Green Room Villa. The 1,500-square-foot, four-bedroom property—the only vacation rental in the sleepy surfing village of Teahupo’o—practically opens up to the water and offers a unique place to rest your head. The main house is shaped like an octagon, with a huge mangosteen tree growing out of the open center, plus a large covered deck, teak flooring, and brightly painted walls that show off the owner’s creativity. The property even works well for a small destination wedding, as there’s a “honeymoon bungalow” near the fruit tree garden. Built on stilts, it sits over a purple-hued, lily-filled pond. It’s also the only room with air conditioning, although breezes keep the main house relatively cool. On a very local part of the island, Green Room Villa is extremely private, providing a relaxed place for your group getaway. Note: the owners require a credit card damage deposit and a three-night minimum stay.

The Bridges of Samaná, also called the “Bridges to Nowhere,” are a string of bridges connecting the small islands that stretch across the outside of Samaná harbor. They are remnants from a project in the 1960s and ’70s by President Joaquín Balaguer to build a restaurant on one of the islands, connected to the mainland by a pedestrian bridge. The restaurant never opened, but the bridges and the shell of the building remain as curious relics of recent history.

Home of the Venice Film Festival, the Lido is also where you’ll find Venice‘s beaches—Shelley and Byron went horseback riding here back in the day—as well as the Grand Excelsior Hotel, whose bar is often crowded with celebrities during the festival (and other times of the year, as well). If you’re a classic film fan, the hotel might look familiar: Luchino Visconti’s Death in Venice was shot here. The island has a decidedly lively feel compared with Venice itself, less a museum piece and more a buzzing destination, popular with Venetians and visitors looking to spend a day by the sea.

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.

The Hyatt brand is world renowned for its service and experience. Their Maui property checks all the boxes for creating the perfect island vacation. From the beautifully executed integration into the ocean environment, to the services and activities at your flip flopped feet, life’s stresses give way to island time the moment you arrive. Close enough to Lahaina town to skip a car rental, yet buffered from the distractions of the world, it’s a great balance in one location. The onsite restaurants are top notch, easily keeping your calorie intake therapeutic. The bars offer a wonderful mix of island cocktails to melt away any residual tension from your stand up paddle board lesson. The little bay on the south end of the resort is home to a healthy group of huge sea turtles, easy to paddle up to in a kayak or board. Walking everywhere is easy and entertaining. Whaler’s Village is just a mile up the beach on a paved path the takes you through some of the other resorts in the neighborhood. Rooms are crisp, spacious and have some ocean views. The resort is medium-sized so you don’t feel overwhelmed by the physical plant. Speaking of plants, there are hundreds of native flora dotting the grounds. Also wondering about are flocks of flamingos and penguins. The Hyatt is a first-class operation leaving you free to relax to your heart’s content.

This beautiful one-mile stretch was donated to the people of the Virgin Islands by Arthur Fairchild, a benefactor of the islands who’d made his fortune on Wall Street before retiring here. The usually calm waters of the heart-shaped bay make the beach the most popular on St. Thomas. Rent beach chairs and floats, and pick up lunch from stands selling burgers, pizza, and other snacks. Lifeguards are on duty every day.

This private island features stunning views of Mount Otemanu and Matira Bay from its own motu just a few minutes’ boat ride across Bora Bora’s truly stunning fifty shades of blue (one minute it is turquoise, the next emerald or aquamarine) from sister resort Sofitel Marara. The private property is the perfect pick for romantic getaways (it’s geared toward couples, and children are not allowed). Privacy and intimacy are emphasized here with only 31 bungalows (20 are overwater, another 10 are located on a lush garden setting on a hill with stunning views) and one luxury villa that while not overwater, features direct lagoon and sandy beach access and a private jacuzzi (the only one on the property). There is no swimming pool, but guests can use the pool and all amenities at the Marara resort via free water shuttle. Should you not wish to leave your little slice of paradise, however, the onsite Manu Tuki restaurant does excellent French Tahitian fare; order lobster anything. There is also a bar, the Mako. Whether staying overwater or on the hill, the layout is the same, and all rooms feature contemporary Polynesian decor, gorgeous wood floors, and luxury toiletries in oversize bathrooms. Overwater bungalows also boast glass viewing panels in the floors and direct access into the lagoon. Make sure to book the “Romantic Soiree” for one night. It combines sunset champagne on top of the hill, followed by a romantic dinner on the beach under the stars. The breakfast delivered by canoe also is a must.