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  • The islands of Tahiti have given the world a lot of popular ideas: This is the birthplace of the overwater bungalow, of surfing, the tattoo, and also . . . the food truck? Yep! Well, maybe not officially, but dozens of years before food trucks became popular, Tahiti was rocking the game with their roulottes. These trucks, which serve everything from traditional island fare to cheeseburgers, pizza, and Chinese food, can be found all around Tahiti, but the greatest concentration is in Papeete, where dozens of the colorful trucks congregate at Vaiete Square. Come for dinner or dessert.
  • Captiva, FL 33924, USA
    To reach this state park off the north end of Captiva Island, you’ll need to travel by private boat or Captiva Cruises ferry. Once there, though, you’ll find 2,400 spectacular acres, including nine miles of pristine beach perfect for shelling and swimming. Keep your eye out for manatees and dolphins, which are often spotted in the surrounding waters. If you’re feeling adventurous, you can even pitch a tent or rent a primitive cabin and spend the night in the real Florida.
  • 75-5699 Alii Dr, Kailua-Kona, HI 96740, USA
    Scandinavian Shave Ice is Hawaii Island’s most iconic purveyor of the frozen treat—though it’s not quite so big a deal on this island as some of the others. That said, Scandi’s is everything you want your shave ice shop to be. Dozens of flavors to choose from, including some with no added sugar? Check. Choice of ice cream for the center? Check. Snow cap and other, more exotic, toppings available (like li hing mui powder or mochi)? Check. Sassy servers? Check. The result is a carefully sculpted ball of colorful ice the size of your head (go for the small size!), with a soft but cohesive texture, flavors more subtle than they look, and the ice cream in the center rather than the bottom—meaning you get to it even quicker! Yum.
  • 76-6246 Ali'i Drive
    This tiny joint on the Big Island serves what many consider the planet’s best poke (raw-fish salad). In fact, Yelp ranked it No. 1 among America’s top 100 places to eat in 2014. Go traditional with just salt, limu kohu (seaweed), and inamona (a roasted-candlenut relish) for toppings. Or opt for a more contemporary twist with anything from onions to avocado aioli, perhaps paired with a side of crisp kimchi cucumbers. Be forewarned: This casual spot runs on island time so don’t expect exact adherence to business hours.
  • Front Street Cockburn, Cockburn Town TKCA 1ZZ, Turks and Caicos Islands
    The only museum on the Turks and Caicos Islands sits on the historic Front Street of Cockburn Town, on Grand Turk. Occupying Guinep House, one of the area’s oldest standing buildings, the museum displays artifacts from the Molasses Reef shipwreck, a sunken caravel found off West Caicos. The ship, which dates from the early 1500s, makes this is the oldest European wreck to be excavated in the Americas. Salvaged items on display include cannons, pieces of the ship’s hull, and a variety of tools. There are also exhibits on local slavery and the indigenous Taino people who originally lived on the islands.
  • Lion's Head, Signal Hill, Cape Town, 8001, South Africa
    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.
  • Providenciales, TKCA 1ZZ, Turks and Caicos, Turks & Caicos Islands
    In the late 1700s, Cheshire Hall Plantation was one of the handful of cotton plantations operating on the Turks and Caicos Islands. During its heyday, the estate spanned thousands of acres, with hundreds of enslaved people working in the fields. Poor growing conditions led to its decline. Today, you can explore the scattered ruins, including remnants of the Great House, which was built from cut limestone. The $10 admission fee includes entrance to the site and a 30-minute guided tour. Cheshire Hall, conveniently located near downtown, offers the best-preserved colonial-era ruins on Providenciales, though Wade’s Green Plantation on North Caicos is the best preserved site of all the islands.
  • 2 Piazza Cerio Ignazio, Capri, NA 80073, 80076 Capri NA, Italy
    Ready-to-wear and made-to-measure dresses, shirts, pants, and skirts are just some of the beautiful things you will find in this pretty store. Around the corner from the flashier names on the Via Camerelle and a short stroll down the hill, the family-owned Laboratorio Capri is where Michele and his mother design and sew for movie stars as well as Capri locals. Shop the sandals and bags, whisper-weight scarves printed with images of old Capri, and colorful jewelry that will remind you of the island.
  • 300 Gravier St, New Orleans, LA 70130, USA
    This English-inspired hotel has been the place to stay in New Orleans for basically forever—well, since it opened in 1984, at least. It’s plush without being pompous, stately without being too serious, though it should be said that this is the kind of place where gents might wear a pocket square and watch fob and feel right at home. The $8 million art collection, which includes original works by Reynolds, Gainsborough, and Huysman, is museum-worthy (you can even take an audio tour), and the 4,500-square-foot spa, part of the 2012 $22 million renovation, is one of the city’s most luxurious. Other notable upgrades include the lobby cocktail bar—a more feminine alternative to the leather-clad Polo Club Lounge, and an outdoor pool.
  • Maras 08655, Peru
    Tours of the Sacred Valley, and the entire Cuzco area, often feature side trips through gorgeous landscapes like Moray, an archaeological site with remarkable concentric agricultural terraces. It’s believed the Incas used these terraces—on which temperatures vary 59 degrees Fahrenheit from the top tier to the bottom—as a way to acclimatize non-regional crops for highland cultivation. Even if you don’t find that fascinating, it’s hard not to appreciate the beauty of the spot, and given that this part of Peru is not so heavily visited, it’s a nice escape from the beaten path. The Boleto Turístico covers this admission.
  • 1 Mohogany Run N, St Thomas 00802, USVI
    These links, designed by George and Tom Fazio, offer 18 challenging holes, including numbers 13, 14, and 15, which make up the spectacular “Devil’s Triangle” that skirt the rocky hillside’s ledge above an ocean inlet. The views stretch from this northeast corner of St. Thomas to the British Virgin Islands. The pro shop is fully stocked with equipment and accessories to buy or rent.
  • Kato Mili, Mikonos 846 00, Greece
    Mykonos’s 16 windmills have become iconic structures that can be seen from all over the island. At the edge of town, the Boni Windmill details how and why the windmills worked but is open only for limited summer hours. But you don’t have to go inside to enjoy the beauty of these old forces of wind power: Stand in awe of their survival over centuries and take some great pictures.
  • Tucked behind a religious statue behind the Cathedral of the Holy Family in Tafuna, you’ll find one of the island’s several tia seu lupe, or star mounds. This example, three meters (almost 10 feet) high, is one of the best-preserved and most easily accessible of these mysterious configurations. Believed to have been used in a ritual by tribal chiefs to capture pigeons for an unknown rite, these stepped-stone structures are similar to others found throughout Polynesia.

  • Sandwick, Stromness KW16 3LR, UK
    On the principal Orkney island, some 30 miles from the north coast of mainland Scotland, sits the best-preserved Neolithic settlement in Western Europe. From 3000 to 2400 B.C.E.—long before Stonehenge or even the Egyptian pyramids—Skara Brae was a thriving village, full of farmers, hunters, and fishermen. It was rediscovered in 1850 after a particularly strong storm and now serves as a fascinating tourist attraction, complete with nine surviving Neolithic houses. Outfitted with stone furniture made 5,000 years ago, the dwellings are linked by low corridors, roofed with what are believed to be original slabs of boulder. When you’re done exploring the village, head to the visitor center to view additional artifacts like gaming dice, tools, and jewelry.
  • Wong Nai Chung Gap, Hong Kong
    Amid the hustle and bustle of Hong Kong, it’s hard to believe that nature is always just a short taxi ride away. Opened in 2009 as a designated historic site, the Tai Tam Waterworks Heritage Trail on Hong Kong Island is a picturesque network of idyllic pathways along the dams and pumping houses built by the British in the 19th century. On sunny weekends, you’ll bump into locals with their dogs in tow.