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Rebecca Walker embarks on a spontaneous journey to Bulgaria, guided by locals she connected with both virtually and in real life.

Lanai, a sleepy, 140-square-mile former pineapple plantation, is suddenly in the spotlight. Following the island’s purchase by tech billionaire Larry Ellison in 2012, the bay-facing Four Seasons Resort Lanai underwent a multimillion-dollar overhaul that reduced the number of guest rooms from 286 to 213. The rooms shook off their dated look with mahogany floors and walls clad in slate and teak. Guests can dine at outposts of Nobu and Los Angeles–based Malibu Farm, take private flight lessons and horseback-riding excursions, or book one of the resort’s wellness-focused retreats.

The Aloha State is a foodie haven that’s unlike anywhere else, thanks in large part to its bounty of fresh, local ingredients. From poke to ramen to Portuguese-Chinese fusion served with a helping of traditional shave ice, you won’t be able to decide on the best place to eat in Hawai‘i.

In Maui, visitors are spoiled for choice when it comes to hotels. The island is home to everything from plantation-style B&Bs to sprawling beach resorts with floating restaurants, offering something for every type of traveler, whether they care most about spacious rooms, outdoor pools, or ocean views. Find family-friendly elegance at the Fairmont Kea Lani; an artsy, boho-chic vibe at Andaz Maui at Wailea Resort; or utter luxury at Four Seasons Hotel Lanai, a sanctuary on a nearby island that was once home to the world’s largest pineapple plantation.

Inside the city’s most innovative restaurants, maverick chefs are defining modern Czech cuisine.

In 2012, one of the world’s richest men—Oracle founder Larry Ellison—bought 97 percent of the island of Lanai. The single sweeping deal (reputed to cost $300 million) included the exquisite Four Seasons Resort, overlooking a marine reserve. The resort’s dining experience par excellence is Nobu, where celebrity chef Nobuyuki Matsuhisa presides over the perfect marriage of Japanese dishes and Peruvian ingredients. Kick things off with crispy Brussels sprouts or scallops with jalapeño salsa, then move on to sushi, hand rolls, or Wagyu beef. Save room for the Bento Box dessert with green tea ice cream and chocolate flourless cake. Or go old-school, if it’s on the menu, and order the mochi pound cake backed by yuzu-cherry jelly and peanut butter ice cream.

On a trip with a young traveler in tow, a writer reflects on her first Venice adventure—and how it changed her life.

Hiking in this enchanted land is a must, with options varying from light to vigorous. Accessible all-season terrain is a paradise for outdoor enthusiasts who relish canyon lands, peaks, and elevation inclines—not to mention pristine air and picturesque tableaux. Expect to see flawless aspen groves and wide panoramas of Santa Fe and the surrounding desert, and don’t forget to carry water.

Local flavors, stunning views, and fine wines: Cape Town has far more than these great experiences, but start here. Active travelers will delight in the number of outdoor experiences by land and sea. Travelers focused on culture will enjoy the variety of local markets and dining options. These are the activities you can’t miss before departing Cape Town.

In search of a flightless, sex-crazed, and rarely seen parrot in a land once ruled by birds.

St. John is the least developed and most sparsely populated of the three main islands in the U.S. Virgin Islands. That’s not surprising, since more than half its land is protected as a U.S. National Park. Most visitors reach St. John by ferry from St. Thomas, landing at the dock in Cruz Bay, St. John’s main settlement. A village with only a few thousand residents, Cruz Bay has gained a reputation as an upscale retreat for movie stars and other high-profile people looking for a secluded getaway.

It all started back in 1956, when businessman and conservationist Laurance Rockefeller, who had bought extensive land holdings on St. John, opened the low-key but luxurious Caneel Bay Resort. It’s still going strong, and visitors can stop in for lunch and a swim in the beautiful bay. Rockefeller later donated much of his estate to the national park.

Snorkelers should make time for an underwater tour in Trunk Bay, where the National Park Service maintains a submarine snorkeling trail. And no sightseeing drive around the island is complete without a stop to see the fabulous panoramic view from the Bordeaux Mountain Overlook. Back in the town, the boutiques at Mongoose Junction offer one-of-a-kind souvenirs, while Cruz Bay Landing is a perfect spot to grab lunch and drinks.

Jordan is an ancient land with enough historic sites to spend a lifetime exploring. If you don’t have that long, head straight for the sublime ruins of Petra, the rose-pink city tucked into a series of canyons—and one of the crown jewels of world heritage. Then, travel north of Amman to the ancient city of Jerash, one of the best-preserved Roman archaeological sites in the world. You’ll also want to see the mosaics of Madaba and nearby Mount Nebo, where Moses first saw the Promised Land, as well as the site where Jesus was baptized and its surrounding Crusader castles and desert palaces.

At just 278 square miles, Singapore (aka Lion City) is tiny, but you’ll never run out of fun things to do. From the Singapore Zoo and its nocturnal animals to the spectacular Singapore Botanic Gardens and Gardens by the Bay, nature is always on show. But it’s well worth heading inside to the temples, churches, mosques, and museums to learn about the country’s diverse history.

Live like a local and seek out sunny moments surrounded by greenery. Pack a picnic, put on your walking shoes, and stroll these wonders like the Parque del Retiro, the Parque del Oeste, and the botanical garden.

A weekend in Marrakech offers just enough time to take in the Red City’s gardens, the medina, and to tumble through the city’s souks and boutiques, your arms filled with purchases. Of course, the food: from traditional Moroccan dishes to European-inspired meals, and plenty of local red wine. Don’t miss a night of food stalls and snake charmers at Djemma el Fna. Tempting as it may be to stay put in Marrakech’s oldest section for the weekend, leave the medina to tour the stunning gardens French painter Jacques Majorelle left behind, and the museum dedicated to legendary fashion designer Yves Saint Laurent. And do go to a hammam on day one because, really, you’ll quickly see why it should be your daily habit while in town.