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Blending a cheerful, laid-back spirit with a splash of formal elegance, The Reefs Resort & Club is uniquely Bermudian. Staff greets you with a rum swizzle upon arrival at the family-owned and operated property, then whisks you up to a room where bright botanical prints complement crisp white linens, deep wood tones, and tile floors, and windows offer views of the Atlantic’s turquoise-tinged waves. Days are spent indulging in frangipani salt scrubs and ayurvedic massages at the spa, sitting in on a sunrise yoga session on the beach and hitting the links nearby, or simply napping on a chaise at the freshwater infinity pool. Sited to capture awe-inspiring vistas of the water, limestone cliffs, and lush vegetation that surround the resort, three restaurants serve classic continental fare, but more adventurous types can rent a scooter across the street to sample the local food scene on a culinary tour of Hamilton and St. George.

The Coronado Bridge links San Diego to Coronado Island—and the present to the past. In the span of just 2.12 miles, you’ll travel from the digital age to a century when “electrified” hotels were practically unheard of. When the Hotel Del Coronado debuted in 1888, its electric lights and telephones made a sensation—as did its resplendence. In 1892, a young guest named Noel proclaimed in a letter to her family back east that “the red and the white between the bluest sky and the bluest water is like a beautiful dream in a fairy story.” Legions of A-listers have checked in ever since, as a who’s who of vintage portraits attests. But while a stay here is delightfully nostalgic—featuring bike rentals, beachside cabanas, and evening clambakes—the 757-room hotel doesn’t live entirely in the past. Take advantage of its upscale spa, spin classes on the beach, and restaurants serving updated takes on coastal cuisine along with creative cocktails. In the historic Victorian Building Suites, you’ll find modern coastal-chic interiors, streaming TVs, and, of course, Wi-Fi. The Beach Village Suites include additional modern luxuries—like a Sub-Zero fridge and dedicated concierge to help you fill it.

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.

The real voyage of discovery consists not in seeking new landscapes, but in having new eyes. ~ Marcel Proust. For my inaugural highlight on AFAR, I am starting with my wife’s favorite quote, and a local sight in Chicago. Sometimes people feel they must jet off to some far off exotic place in order to ‘travel.’ However, if you gaze anew at your immediate surroundings with fresh eyes, you will discover an entire host of wonderful surprises. Here we have Cloud Gate, located down in Millennium Park, back before they buffed out the seams. The contrast between the organic form of ‘the bean’ and the structured grid lines, along with the warped fun house mirror quality of the city, makes this a truly unique destination.

Begin your perfect beach day with a stop at this snackbar on Positano’s Spiaggia Grande for a sweet brioche and a cold cappuccino freddo. In the afternoon, come back for a scoop of gelato or a chocolate-dipped ice cream–bar snack. At the end of the day as the sun drops behind the mountain and the day-trippers leave, perch on one of the high stools at the cocktail bar and sip a cold gin and tonic or draft beer. The bar is attached to a formal restaurant that overlooks the beach.

Gandhi Smriti, previously called Birla House, is now a museum dedicated to Mahatma Gandhi, the man many consider the “Father of Indian Independence.” Gandhi lived in the house during the last several months of his life and was assassinated here in January 1948. View the modest rooms where he spent his days, and stroll the same prayer grounds where he held a nightly congregation. A visit to Gandhi Smriti offers insight into the last 144 days of Gandhi’s life, during one of the greatest periods in Indian history.

Located on an uninhabited island near Qaqortoq, the Uunartoq Hot Springs is the country’s only naturally heated outdoor spa. These waters have been a destination for locals and travelers alike for over 1,000 years—legend has it that Leif Eriksson bathed in the springs before beginning his expedition to North America. Plan on taking half a day to journey to the island and back if you want to splash around in the great outdoors while enjoying the unparalleled mountain and iceberg views.

When local restaurateurs Brooks Reitz and Tim Mink shut down Saint Alban, Charleston was distraught. They had something different in mind for the space, however, and replaced their airy, all-day café with a cozy steak house straight out of the 1950s. Much like its predecessor, Little Jack’s has quickly established itself as a neighborhood favorite. It’s open every day from 11 a.m. until late in the evening and serves classic, meat-heavy dishes (steak, sliders, pastrami) alongside seasonal salads. A solid menu of classic cocktails (Harvey Wallbangers, sidecars) rounds out the throwback experience.

Located less than an hour from Dresden in Saxon-Switzerland National Park, the Bastei is a jagged outcropping of sandstone rocks that once served as the foundation for Neurathen Castle. While the castle is mostly gone now, its bridge (known locally as Basteibrücke) remains one of the park’s major highlights. Initially made of wood but rebuilt with stone, it clocks in at 250 feet and leads directly to the castle ruins, offering peerless views of the Elbe Sandstone Mountains, the Elbe River, and the Königstein Fortress. For a small entrance fee, visitors can walk its length, then refuel at the Panorama Restaurant on the other end. Active travelers may even want to attempt the Golden Triangle hike between the Bastei, Wehlen, and Kurort Rathen, which also passes the ruins of Stadt Wehlen Castle.

At this 11-acre organic farm outside Aix-en-Provence, American Lisa Pepin and her French husband, Johann, lead truffle-hunting tours in English during both the summer (May to September) and winter (mid-November to mid-March) truffle seasons. Guests search for “black gold” while learning about how truffles are harvested and truffle dogs are trained, then enjoy a sampling of fresh truffle hors d’oeuvres, Champagne, and Les Pastras’ olive and truffle oils. During the hunt, the Pepins regale their visitors with stories of success and sabotage, while teaching them the difference between a Provençale truffle and its inferior Chinese counterparts, and how to properly clean, store, and cook with truffles. Johann’s enchanting tales and Lisa’s joie de vivre will have you coming back for more, only next time to stomp grapes, harvest olives, or simply shop the farm’s delicious products.

Four thousand modern art pieces throughout public areas and guest rooms liven up this Pudong waterfront hotel, which opened in April 2013. The highlight is the lobby’s Glass Murals, made from almost 72,000 mosaic tiles and inspired by local artist Miao Tong’s painting Sound of the Wind. Elsewhere in the lobby, guests will encounter Chinese screens, sculpted furnishings, and bronze tones that mimic the glow of sunset on the river. Rooms have taupe furnishings, with flashes of indigo and lotus-green, and abstract ink paintings of traditional Chinese garden landscapes. Some have hypnotic Huangpu River views. As with many hotels in Pudong, the property is set within a larger complex, in this case the 61-acre mixed-use Harbour City development.

One of Dubrovnik’s oldest fortresses stands atop a 100-foot rock, guarding the western land entrance to the Old Town. Vigilantly turned toward Venice, it serves as a monumental tribute to Dubrovnik’s foresight, encapsulated in the motto of the Ragusan Republic engraved above the main entryway: “We do not sell our liberty for any gold in the world.” After entering the Old Town through the Pile Gate, walk down to Kolorina Bay and climb the stairs to the fortress. Because it’s far less busy than the city walls, the theatrical space offers a more intimate way to experience Dubrovnik’s history and charm, with breathtaking views to boot.

Occupying three whitewashed colonial buildings sheltered from the bustling streets of Old Town Cartagena, Casa San Agustín sits on the site of a former aqueduct and channels its heritage with a swimming pool that tunnels through its stately remnants. Inside, common spaces feature a mix of Colombian art and artifacts with contemporary wicker furnishings and marble floors. The 20 rooms and 10 suites are cozy and a bit more polished than those found at other historic properties nearby: Units feature 200-year-old wood-beamed ceilings and iron canopy beds topped with Frette linens; some have patios with hot tubs or brick terraces with views of surrounding buildings. But there’s plenty of space to unwind throughout the property, namely a library with original frescoes and a lounge with a long wooden bar and ceiling-high wine cabinet. It’s a good idea to make reservations in advance for dinner at Alma, considered among the city’s best restaurants, where the upscale international cuisine includes fresh ceviche and dry-aged beef cured on-site.

Somewhere between a luxury yacht and a royal residence, the Hotel Lungarno seems like the sort of place where Audrey Hepburn’s Princess Ann, of Roman Holiday, would have felt right at home. A 16th-century private residence on the southern banks of the Arno, next to the iconic Ponte Vecchio, the hotel was the first entry into the Ferragamo family’s Lungarno hotel collection, lovingly restored by renowned Florentine architect/designer Michele Bönan. With rich navy carpets, stained-wood furnishings, crisp white linens, and as many large, river-facing windows as he could get away with. It comes as no surprise, either, that the house restaurant is considered among the best in the city. Even if the food and the atmosphere weren’t top-notch (and they are), the sunset views of the city lights reflected in the river would be worth it.

Conservatorium has a fascinating past. It started as a bank and then became a music academy before renowned Italian designer Piero Lissoni transformed it into a hotel in 2012. The building itself harmoniously blends old and new, with modern steel beams and glass walls complementing original brickwork and wooden beams. The hotel houses one of the city’s largest and most decadent spas—a subterranean temple to holistic wellness, with its own hammam, Watsu pool, lap pool, and more. Its restaurants and bars are also among the trendiest and most highly acclaimed in the city. Upon arrival, each guest is assigned a personal host to offer recommendations, reservations, and historical tidbits.