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Sailing is Anguilla’s national sport, but it’s also the best way to explore the island’s dreamy Caribbean shores—and the best way to explore its marine life while in transit. Spend the day with Tradition Sailing Charters, gliding across iridescent blue waters on a 1978 50-foot sloop, drifting from one cay to another. You’re welcome to watch and learn how to sail if you’re a newbie, or to participate if you have experience. After a lunch stop at the only restaurant in Prickly Pear Cays, get underwater to check out this reef-protected bay where sea turtles, blue tang, and numerous other tropical critters thrive. There’s also a brown booby colony on land here.

Yes, the natural wonders in this vicinity are worthy of all their superlatives, but so are the accompanying manmade offerings. One is the Southern Fuegian Railway—also known as the End of the World Train—which has been steaming through the area for more than a century. The world’s southernmost train line, it was once used to transport the region’s timber; today the cars carry visitors through the epic Tierra del Fuego National Park, past shimmering lakes and verdant peat bogs.

Put on your comfortable shoes and head to the many trails of Cayman Brac to see wildlife, as well as scenic and geological sights. There is a path for all skill sets. Listen to the mating calls of the parrots flying above at the National Trust Parrot Reserve Hiking Loop, or descend carefully into Peter’s Cave and move through the various layers to discover a truly breathtaking natural wonder. Most hotels have a brochure of all the hiking trails; this includes images, difficulty, and a brief description of each trail.

“I am grateful” is just one of the ways you order lunch at Cafe Gratitude. “I am whole” is another; as is “I am glorious.” Every dish on the menu has a name like this, and whether you’re in the mood for gratitude (the community bowl with shredded kale, black beans, garlic tahini, and quinoa), wholeness (the macrobiotic bowl with braised butternut squash, adzuki beans, and sautéed greens), or glory (the blackened tempeh Caesar wrap), Cafe Gratitude guarantees your meal will be as much an experience in self-affirmation as a delicious jaunt into vegan fair. The Venice location is eclectic in patronage and airy in design, while the swanky Larchmont restaurant draws a more Hollywood cast of characters. Other locations include the Arts District, Newport Beach, Beverly Hills, and a little further south in San Diego. For larger events, Cafe Gratitude can also be hired for catering services.

Wonderful catamarans that you can rent right off the beach.

The andBeyond Lake Manyara Tree Lodge is the only permanent lodge in the Lake Manyara park. This tree house hotel emphasizes the mahogany forest where it is located in Lake Manyara National Park. The original nine suites of the Lake Manyara Tree Lodge are all built on stilts with large decks suspended above the forest floor crafted from local timber and makuti palm fronds. A family suite takes that model and supersizes it, creating a second bedroom for the kids.

While here, arrange a tour with Deeper Africa to Lake Manyara National Park. Guides will take you to see birds and primates in their natural habitat, including silvery-cheeked hornbills and vervet monkeys, as well as black mamba snakes, wild orchids, and countless butterfly species.

Cane’s chef and owner Paul Yellin grew up on Barbados, and he drew on this experience while putting together this bar and restaurant: the menu is full of Caribbean dishes, and the space is decked out with palms, corrugated metal, and bamboo. Another Barbados-inspired touch? The heavy presence of rum at Cane. The bar houses bottles from across the wold, and the drinks menu serves classic rum-centric cocktails like Zombies and Painkillers alongside more creative concoctions.

This funky spot stands out among Amsterdam’s many urban “beach bars.” You can laze away a sunny afternoon at one of the picnic tables or chairs set up on a wide stretch of sand. Cocktails and beer slake your thirst, while decent pulled-pork tacos, burgers, and poke bowls keep hunger at bay. If the weather isn’t agreeable, the café—located inside a converted warehouse—strikes all the right hipster notes: Think distressed, graffitied concrete walls; leather sofas; vintage television sets; and groovy lighting. An adjacent warehouse hosts all sorts of events, from flea markets to film screenings to dance parties.

A year ago I had dinner at the Clifton, then under the supervision of Tucker Yoder. Mr. Yoder was elsewhere that evening, but I spent several hours at the “chef’s counter” in the kitchen, watching executive sous-chef Jarad Adams work his own delicious magic. Naturally Mr. Adams was meticulous with his food prep, but he was also surprisingly generous with his time for me. Imagine my delight when I returned this year to find Mr. Adams had been promoted to Executive Chef. On this visit, Mr. Adams’s tasting menu showed the same attention to detail as I remembered, but with a greater sense of adventure — even whimsy. From the amuse bouche (a spoonful of polenta topped with pork belly, apple, and a sprig of fennel) all the way through to the sticky toffee pudding with candied pecans, dates, and caramel ice cream for dessert, I was enchanted. The tasting menu consists of four courses and varies by the season. My first course was a toss-up between the butternut squash and apple soup and the shaved winter vegetable salad with hazelnuts, black cocoa, and a buttermilk dressing. I had no regrets about my choice of the salad, especially as butternut squash was the foundation of my next course: the most perfectly seared sea scallop I can remember. From there it was onto monkfish with beluga lentils, with Brussels sprout leaves dancing on top. Mr. Adams knows what he’s doing in the kitchen, and the Clifton — and Charlottesville — is lucky to have him.

After five days of cooking classes--learning from Estela Salas Silva and Jon Jarvis how to make typical Poblano dishes including sopa de tortilla, crema de chile Poblano soup, tamales, tinga, sopes, pipian verde and pipian roja, mole Poblano, chipotles en conserva, ensalada de nopalitos, and more--the payoff includes a diploma, a loose-leaf folder of recipes, and a deeper knowledge of central Mexican cuisine, culture, and history.

Visitors take their best Chicago photographs in front of the iconic Millennium Park sculpture called Cloud Gate (known colloquially as the Bean, for its shape). Conceived by British artist Anish Kapoor and constructed from 168 stainless steel plates with no visible seams, the polished surfaces of this 33-foot-tall sculpture reflect infinite variations of the Chicago skyline. The work’s design was chosen from among more than 30 others commissioned by the city, and it was inspired by liquid mercury.

The Grand Tour of Switzerland includes thrilling bends and scenic views at every turn, and five of its famous alpine passes stand out—literally—among the rest of the route. They are engineering wonders that often overlook natural wonders as well. The Flüela Pass, which connects Davos and Susch, reaches a height of 7,818 feet. Your ascent through alpine forests delivers views of the valley below on a route that Avis ranked number 4 on its list of the “world’s best roads.” The Julier Pass is lined with picturesque lakes and ends at the village of Tiefencastel, with its historic, and equally picturesque, Church of St. Stefan. The San Bernardino Pass in southern Switzerland follows a route used since the 15th century and sits on the border between the country’s German and Italian regions. With its serpentine twisting path, the Tremola Pass in Gotthard is a wonder of 19th-century road design. After navigating its many twists and turns, enjoy one of the famous sausages sold from a hut at its summit. Finally, if the Furka Pass looks familiar, it’s likely from its big-screen appearance in Goldfinger. Fortunately as you drive to the highest point on the Grand Tour, at 7,969 feet, you’ll be able to simply enjoy the scenery without any villain in pursuit.

It’s a crime not to order a cocktail (boozy or virgin) at Spago’s terrace bar, situated next to the famous infinity pool on Marina Bay Sands’ breezy veranda. The drink menu is just as beautifully curated as the decor, featuring more than a dozen original cocktails, over 600 bottles of wine, and an extensive champagne list. Celebrity chef Wolfgang Puck put together the selection of bar bites, including Spago L.A. originals like the bigeye tuna tartare cones. For a full dinner menu in an even more refined setting, book a table in Spago’s glassed-in formal dining room to enjoy dishes like chirashi sushi from the legendary Tsukiji Market and pan-roasted snapper laksa.

The ancient Romans used aqueducts to carry water from distant springs into central Rome. As the empire decayed, so too did these ambitious public works. When Rome experienced a renaissance—not to mention a population boom—in the modern age, popes took cues from the emperors before them and repaired these ancient water channels. To celebrate their grand projects, they built massive public fountains like the Fontana dell’Acqua Paola on Janiculum Hill. Dubbed er fontanone (“the big fountain”), this 17th-century structure was commissioned by Pope Paul V to commemorate the repair of the Traiana aqueduct that tapped a spring near Lake Bracciano north of Rome.

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.)