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Set in a row of shophouses—traditional double-use structures with a storefront on the street level, the owner’s residence on the floors above—the New Majestic Hotel is a small gem in Chinatown filled with quirks and contrasts. Colonial design is plentiful, from the vintage Compton fans in the lobby to furniture from the 1920s–1960s throughout. The rooms are a little more free-form. They range from suites with their own urban gardens to attic-style spaces with loft beds and 20-foot ceilings. Then there are the five rooms in which Singapore artists were told to unleash their creativity (Work, one of these rooms, looks like temporary housing, with plywood sections everywhere). Pieces by local emerging artists include murals with hidden messages or displaying pop art influences. The bottom of the rooftop pool has small portholes that look down onto the Majestic Restaurant, one floor down.

Old San Juan may look, at first glance, like a few other charming cities built during the height of Spanish colonialism—Havana or Santo Domingo, for example—but what sets it apart is the extent to which its architectural infrastructure from that era remains visible. It’s the only city that has its original colonial wall almost entirely intact, and both of its principal forts are in excellent condition, remain accessible to the public, and offer panoramic views of the Atlantic Ocean (so bring your camera). Both El Morro and Fuerte San Cristobal are run by the National Park Service; guided tours will leave you with greater knowledge about the era, as well as the forts’ construction and their role in Puerto Rican history. (There are other, smaller forts in and around the capital, next to the Caribe Hilton, and in Luís Muñoz Rivera Park, plus Fort San Juan de la Crúz in the nearby town of Cataño.)

The Castelo de São Jorge, is one of the Alfama neighborhood’s most historically significant monuments. Plan a visit late in the afternoon so that you can explore every nook and cranny and learn about the castle’s abundant history. Stay for golden hour so that you can capture the light as it dances on the castle walls, and later to watch the sunset dip below the horizon.

Petra flourished more than 2,000 years ago, trading with Rome as an equal before being abandoned after a series of earthquakes in the 4th and 6th centuries C.E. It wasn’t until the 19th century, when European explorers “rediscovered” it, that the ancient city returned to the public consciousness. Now, visitors can walk down the narrow canyon of the siq to the city entrance—as dramatic an approach as any to a tourist attraction on the planet. The canyon opens up onto the carved facade of the Treasury, Petra’s most iconic site. From there, you can explore the cliffside tombs with their colorful bands of sandstone, the Street of Facades, and the amphitheater hewn from living rock. The ancient center lies some distance off, along with the splendid old Monastery, which sits at the top of a steep but rewarding climb. Consider buying a three-day ticket and visiting at different times of day to enjoy the changing light—early in the morning is best for the Treasury, while late afternoon is better for the Royal Tombs.

A pilgrimage to this enchanting park is a must for any Antoni Gaudí fan. Located atop Carmel Hill to the north of the city, the park was inspired by English landscape gardens, but its fantastical elements make sure you know it was created by Catalonia’s most eccentric architect. Though there are multiple entrances, the most impressive is via a grand staircase guarded by an enormous, mosaic-tiled dragon. It leads to a sprawling plaza with a mosaic-covered cement bench stretching some 328 feet around the perimeter. Park Güell was originally designed as a gated residential development, but it failed; a show home built to lure buyers is now the Gaudí House Museum (not included with park admission). Visitors should reserve an online ticket to avoid lines.

The system of canals and chinampas (cultivated artificial islands fashioned from the area’s swampy soils) that has survived in the far-south neighborhood known as Xochilmilco once stretched all the way to the Centro. To this day, the community is known for its plant nurseries and vegetable gardens. These ancient landscapes now contribute to what has become one of the most singular pleasure gardens in the world, where visitors hire “gondoliers” to propel boats known as trajineras as they sail these channels in the company of floating mariachis and food vendors, partying teens, and extended families out for a picnic lunch. Since a tour is usually a four-hour-plus investment (it flies by), ask your oarsman to take you to Xochimilco’s more-rural precincts, where you’ll enjoy marvelous quiet, far from the madding crowd, in the company of cranes, curs, and picturesque cornfields.

Lamu, one of the most magical destinations in Kenya, is famed for being the oldest and best-preserved example of a Swahili settlement in East Africa. The Old Town has been inhabited for over 700 years and is made particularly beautiful by the assortment of Swahili, Arabic, Persian, Indian, and European architecture. Since 1370, different cultures have been lured to Lamu, making it an important trading port along the East Africa coast. Nowadays it enchants visitors with its narrow cobbled alleyways, wandering donkeys, weather-beaten stone buildings, hidden courtyards, and the sight of rustic wooden dhows sailing in the distance. Visit the local mosques, wander the streets of quaint Shela village, sail over to the luxurious Majlis Resort for a swim and a cocktail, or while away the hours on an ornate roof terrace.

Tepotzlán is the perfect day trip from Mexico City. A strange and wonderful mixture of colonial heritage and architecture, new age spirituality, and peaceful mountain vistas, this town certainly deserves its UNESCO designation as one of Mexico’s “pueblos mágicos.” According to legend, this town sits on the birthplace of the Aztec serpent god Quetzacóatl, and its impressive pyramid (“Pirámide de Tepozteco,” built in honor of Tepoztécatl, the Aztec god of the harvest) is now a gathering place not only for pre-Colombian enthusiasts, but seekers of all kinds who believe it to be a generator of groovy vibes. The pyramid is located at the top of of a cliff above the town and the 2km hike is recommended only for the physically fit. If you do go, start out early before it gets too hot and bring plenty of water. Tepotzlán also offers plenty of more down-to-earth attractions, like a beautifully preserved historic center, a selection of nice restaurants and hotels, a bustling crafts market, an interesting monastery and museum, and a world renowned cooking school (lavillabonita.com). For breathtaking views of the valley and cliffs, have a meal at La Sibarita, which is perched on a hill high above town.

A city of red-tiled rooftops, pine- and cypress-shaded hills, and sparkling turquoise waters, the Old Town of Dubrovnik stuns with both its architecture and scenery. Its surrounding stone walls, built between the 11th and 13th centuries to protect the city from war and epidemics, stretch for a full 1.3 miles, comprising an immense system of forts, bastions, and walkways that offer breathtaking views. Hike along them, then be sure to check out the Lovrijenac Fortress, built atop a 100-foot rock looking out toward Venice (Dubrovnik’s historic rival). The Old Town’s main street of Stradun, known locally as Placa, is also worth exploring. It’s especially nice in the late afternoon, when the sun shines off the historic buildings and swallows soar in the blue sky above.

Before America had the Outback Steakhouse, Australia had The Overlanders in Alice Springs, a Northern Territory institution housed in the building that served as Alice Springs’ first town hall. Opened by Daphne Campbell (now Calder) and named after the Australian drama The Overlanders in which she co-starred, the place is part restaurant, part museum where antique leather saddles and framed playbills showcase the ranching and film history of the town. Celebrity fans should look for familiar autographs on the “windmill of fame.” Besides the decor and heritage, locals and tourists flock here for the quintessential cuisine, exemplified in The Drovers Blowout menu: a four-course meal that includes a platter of crocodile vol-au-vent, kangaroo fillets, buffalo medallions and wild camel served with plum sauce.

Crowds may swarm upon it daily from sunrise onwards, but exposure hasn’t dulled the impact of the largest religious monument in the world. Commissioned by King Suryavarman II in the 12th century as the centerpiece of the mighty Khmer empire, the structure is inspired by Hindu sacred design and is estimated to have taken around 30 years to build. The biggest surprise upon visiting might be learning that the vast complex of spires, moats, frescoes, cloisters, and balustrades was constructed in such speedy fashion. You won’t be alone while witnessing it, but sunrise over the iconic temple remains one of the essential experiences in Southeast Asia. A return in the afternoon when the camera-toting hordes have dispersed is also advisable.

The Great Wall of China runs more than 21,000 kilometers (over 13,000 miles), not as one continuous wall but rather as fortified wall sections. Some of the sections date back more than 2,500 years, though only 8.2 percent of the existing wall is original. The Mutianyu Great Wall is one of the more accessible portions. Hike (because that is what you’ll be doing, even on the wall itself) up the Great Wall, then slide down the side of the mountain on a toboggan. Alternatively, explore the Simatai Great Wall, which retains a more authentic feel—save, of course, for the fake water town at the bottom. Even more remote is the Jiankou section, which is largely unrestored, so book with an experienced group like Beijing Hikers or Wild Great Wall.

Described by writer Tahir Shah as the “greatest show on Earth,” no visit to Marrakech would be complete without a visit to the famous night market on the Djemaa el Fna. Arrive before sunset and park yourself at one of the various cafés with terraces overlooking the square to watch performers set up; then venture into the fray in search of adventure. Silk-clad acrobats, wide-eyed storytellers, sly snake charmers, jangling belly dancers, and capricious monkey handlers all emerge from the darkness, ringing the edge of the food stalls with their own special brand of entertainment. When you tire of the heckling, prowl the market in search of good things to eat: bite-size morsels of grilled lamb rubbed in cumin, sardines fried in chermoula, peppery snails, and sheep’s heads for the brave. Then nudge up alongside a family of locals at the table and settle in for the feast. If you’re nervous about going it alone, you can sign up for a food tour with Canadian tour guide and all-round good egg Mandy Sinclair of Tasting Marrakech; she’ll help you find the best stalls while introducing you to the secrets and delights of traditional Moroccan street food.

Witness the destruction wrought by Mt. Vesuvius nearly 2,000 year ago at the archaeological site of Pompeii. The ancient village was frozen in time beneath a blanket of hot ash during an eruption in 79 C.E. Among the ruins that have been uncovered are buildings that shed light on aspects of ancient life both grand and mundane, from the temples, the coliseum and homes with fine frescoes, to public baths, chariot-rutted streets and grain stores which now hold plaster casts of the people who perished that fateful day.

North of Tbilisi, you’ll find some of Georgia’s most iconic attractions: Jvari Monastery and Svetitskhoveli Cathedral, both UNESCO World Heritage sites, located in Mtskheta, the former religious center of Georgia. Then drive along the stunningly scenic Georgian Military Highway to Stepantsminda, commonly known as Kazbegi, where neighboring Mount Kazbegi makes for great walking or biking. Stay at Rooms Hotel Kazbegi in the 6,000-mile high Kazbegi village. This improbably stylish mirage of a mountain lodge was the brainchild of a local gambling tycoon, Timur Ugulava. A minimalist Scandinavian aesthetic (and barely any closet space) dominates inside the serene 156 guestrooms, all with breathtaking views on snow-covered slopes. The public spaces are decorated with fascinating Georgian vintage film posters, old rugs, bookshelves, and leather couches that invite endless lingering. The restaurant does stylish takes on Georgian dishes; don’t miss the khachapuri (cheese pies). There’s also a cozy bar with its own fireplace and cigar menu, a sweeping sun deck, an almost Olympic-size indoor swimming pool, and mountain bikes for the guests. The building is fashioned from metal, glass, and local wood reclaimed from old buildings.