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My friend Andy says you can’t go to Milan without having an evening in Brera, the tiny artsy area adjacent to Milan’s fashion center. Bar Brera is the hangout of choice for expensive liquor and people watching.

Accessible only by seaplane, Kuredu rewards the adventurous with a secluded stretch of powdery white sand on the Lhaviyani Atoll. The resort is popular with dive enthusiasts thanks to its PADI certification center, but water babies of all stripes will find plenty to love, including snorkeling, catamaran sailing, kiteboarding, and private dolphin-watching trips. Those who would rather stay dry might prefer to hit the links: the country’s first golf course is right next door. A range of simple yet comfortable villas and overwater bungalows, many with private pools or Jacuzzis, provide a low-key crash pad after days spent among the waves; couples seeking even more quiet stay in the adults-only section of the property. Housed in a cylindrical domed aquarium on nearby Hurawalhi Island, the much-photographed 5.8 Undersea Restaurant is open for lunch and dinner, giving guests yet another opportunity to get close to their aquatic neighbors.

Though it lacks a beach, this family-owned and professional diver–managed resort on the rocky coast just south of George Town has direct ladder access into the Caribbean. Grand Cayman’s two famous underwater sites, Eden’s Rock and Devil’s Grotto, are just a short swim away, and boat trips offer the option of two daily dives (including night dives). Images by some of the world’s most respected underwater photographers decorate many of the tiled and comfortable smoke-free rooms, some of which have kitchens and private balconies or terraces. The vibe is laid-back; post dive, guests sit by the pool or swap stories at the palapa bar, which has the island’s best sunset vista. Managers Anne Briggs and Lisa Evans, the granddaughters of Sunset House’s founders, make sure everything runs smoothly and ensure visitors explore the best of Grand Cayman both on shore and underwater.

Just minutes from some of the world’s best surf breaks, the Four Seasons has its own surf school offering lessons for all ability levels, from novices to big-wave riders. Surfari Splurge and book a boat trip aboard the Four Seasons’ Explorer, a three-deck catamaran that can get you to some of the area’s most remote atolls. See the Best Every August the resort hosts a week-long international surfing competition that draws both locals and elite athletes such as Tom Curren. You can buy day passes to watch the action. Sleep Therapy Wellness treatments linked to the lunar cycle are scheduled from 10 p.m. to 1 a.m. at the resort’s spa, which sits on its own island.

A signature experience in Negril is to go on a two-hour glass-bottom boat snorkel trip, toward the cliffside or to the nearby reef around Booby Cay. Truth be told, snorkeling isn’t a must if you’re not up for it—but floating on a small boat amid deep jade and turquoise waters and being able to see marine life 20 feet or more below through the glass is a memorable experience. If you do want to snorkel, the cliffside has stunning limestone formations and underwater caves, while the reef is filled with all sorts of marine life, from stingrays to barracuda. A glass-bottom boat ride shouldn’t cost you more than US$20 per person. Look out for Famous Vincent‘s boat—the best pick—or approach one you see resting along Seven Mile Beach, across any reputable resort. The boats—including Famous Vincent—occasionally ride along the cliffside resorts in the mornings or afternoons, looking for anyone interested in an impromptu adventure.

Though not really a tropical island, the indoor resort called “Tropical Islands” outside of Berlin makes for a great (albeit unusual) day trip. Located inside a former Soviet air hanger, the building has been converted into a biosphere with a tropical climate. Inside the resort there is an artificial beach, swimming pools, saunas & a spa, water slides, a small rainforest and even a hot air balloon! To get there with public transporation, you can take a Regional Express train from central Berlin. Trains leave every hour toward Cottbus (depart at Brand-Niederlausitz). It takes about 50 minutes. From the train station, Tropical Islands offers a free shuttle bus for the 5-minute journey to the resort. If you buy tickets at the door, admission to the Tropical World or the Tropical Sauna & Spa complex is 34.50€ for adults and 27€ for children age 6-14. A Kombi-Ticket is valid for both areas and costs 39.50€ for adults and 27€ for children.

During the day, the Piazza San Marco in Venice is an overwhelming flurry of activity, but once the sun sets, you’d be surprised at just how much a sense of ease and languor settles in. Life simply slows down as the crowds depart. Stop by Caffè Florian for a memorable evening. Opened in 1720, this is Italy‘s oldest cafe, and features ornate frescoed and gilded salons, as well as an outdoor seating area for great people-watching. Sip a drink and enjoy Caffè Florian’s live orchestra and singers as you sit under the beautiful night sky, with an illuminated St. Mark’s Basilica in the background. Looking around at my family, I could see total contentment reflected on each of their faces—the most magical and relaxing night of my trip. While not inexpensive, this evening was worth every Euro to me—a night that I will remember fondly for the rest of my life.

Some friends had been hiking in Austria in May and had to cut the trip short because of an unexpected blizzard. After all day hiking in the snow and not prepared for it, we came to a hut that was open to guests run by a woman named Helga. Helga didn’t speak a word of English, but she served us some delicious Mittenwald beer, that tasted like the best in the world. So a few days later, we decided we had to go to the source of this magical elixir, the town of Mittenwald in Bavaria. We went to the brewery and met the proprietors of the restaurant associated with the brewery, Postkeller, where we thought we would have a couple of tastes. Instead, it turned into an all-day affair. We tested the many different varieties of Mittenwald, and our hosts cooked up a roast for us, and we had a great evening of laughs with them.

The hike up Lion’s Head affords incredible views. Since the trail winds around the mountain, you’ll have the unique opportunity to see every side of Cape Town from above. When you start, the ever-stunning Table Mountain will be just to the left, but soon enough, you’ll be facing Robben Island in the distance, with all of Cape Town below. The Lion’s Head hiking trail is eight miles round-trip and takes about three to four hours to complete, depending on your pace. If you happen to be in town during the full moon, be sure to start hiking mid-afternoon and bring your headlamp and a picnic dinner. Along the way, you’ll meet many a local honoring their monthly tradition of hiking up, eating dinner during the sunset, and hiking back down in the moonlight glow.

Most of the year, Punta Cana’s white, sandy stretches of sand are blessed with gently lapping surf, which means that night swimming isn’t as dangerous or daunting an exercise as it can be on other Caribbean islands. Slip into the water near the Westin’s covered pier, and have the ocean all to yourself. Under the bright light of a full moon, you might even catch a glimpse of a sea turtle inching its way along the beach.

The Hotel Telluride is close to town and the slopes but just removed enough from the action to feel like a tranquil mountain getaway. Here, the warm lobby welcomes guests with a large fireplace, comfy couches, and board games, as well as a dedicated check-in area for pets, who are allowed for a small fee and treated to house-made biscuits. Rooms have kitchenettes, private balconies, and humidifiers to combat the dry mountain air, while suites feature separate living and dining areas. It’s been said that The Hotel Telluride also boasts the most comfortable bed in town, triple-sheeted with custom-made linens.

The small, on-site restaurant, West End Bistro, serves a hot breakfast and simple dinner items like kale-and-quinoa salad and Colorado beef burgers—plus freshly baked chocolate chip cookies for an après-ski treat. Guests also have access to a sun deck with hot tubs and outdoor saunas as well as free cruiser bikes and shuttle service to the gondola and downtown Telluride. If desired, the hotel can even arrange for in-room massages or guided day trips to forage for wild mushrooms.

A recent makeover of the Four Seasons Hotel Chicago from Houston-based Rottet Studio did away with the dark and clubby vibe common in older Chicago hotels in favor of a brighter natural palette. Today, the lobby is open and bedecked in oversize floral arrangements; the open-plan lounge there, with its modern glass chandelier, has become a high-end local watering hole known as the Social Bar. The new Adorn restaurant is now a big-night-out dining destination courtesy of chef Richie Farina’s creations that range from a perfectly prepared filet mignon to caviar and eggs. Upstairs, the 345 guest rooms—more than half are suites—feature understated grays and pale greens and come with deep soaking tubs and (if you ask) unimpeded views of Lake Michigan.

This urban icon started as a hippie food truck housed in a surf shop parking lot on Vancouver Island. It has since blossomed into three restaurants, two burrito bars, a taco joint, and two food trucks, located everywhere from Hastings-Sunrise and Yaletown to Gastown and the Financial District. Chef Stefan Hartmann, who once ran a Michelin-starred restaurant in Berlin, now captains these elevated spots along with founder Jason Sussman. Expect nuanced options like chorizo-kale, pork al pastor with pineapple, and chicken with pickled vegetables, all on soft wheat tortillas for six to seven dollars. Also noteworthy are the meat-free dishes like “vegetable scrapple”—a delicious fritter of squash and chickpeas, topped with herbed tomatoes. And don’t overlook the octopus tostada—Tacofino not only sources seafood sustainably but also participates in Vancouver’s Climate Smart program and is working toward being a zero-waste business.

Across the Cumberland River from downtown, residential East Nashville got its first taste of hipster cool in 2016 when this Instagram-friendly bed-and-breakfast opened in a renovated Queen Anne mansion. Like its sister property in Brooklyn, Urban Cowboy’s eight suites and freestanding cabin are each uniquely named—Midnight Rider, the Lion’s Den—and decorated with geometric inlaid woodwork, Southwestern-inspired designs, and handcrafted furniture, plus custom wallpaper and copper and claw-foot tubs. The communal music parlor encourages interaction among guests with a collection of gently worn instruments, as does the all-weather fire pit, where blankets and good cheer are plentiful, especially after enjoying craft cocktails and wood-fired meals at Public House, the property’s on-site restaurant and bar.

Run by the famous Spanish shoe brand, Casa Camper is a stylish boutique hotel neatly situated in the middle of Mitte’s hip fashion and culture district. Designed by Jordi Tió and Fernando Amat—the founder of Barcelona’s iconic design store Vinçon—the devilishly good-looking interior is defined by clean lines and striking furniture set against rust-red walls. The rooms are deliberately minimal, with wooden floors and slick designer furnishings, but are decidedly comfortable and include eco-friendly touches such as water-recycling showers. Instead of an in-room minibar concept, the hotel offers a 24-hour buffet that is free for guests. Plus, the hotel’s prime location ensures easy access to the swanky drinking, dining, and shopping options in the neighborhood.