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Among vacationers who’ve been coming to Grand Cayman forever, there’s a whole faction that essentially camps out at Rum Point all day every day, and you’ll understand why as soon as you see the place. Tucked away, super low-key, and graced with a ridiculously photogenic pier—its perfectly weathered planks cutting a striking figure against the tranquil, turquoise surroundings—this beach is the ultimate spot for settling into a lounger or hammock between water-sports outings. Rum Point’s namesake booze—which used to wash ashore by the barrel, according to legend—is available in all manner of cocktails here, of course. But order at least one mudslide at its spiritual birthplace: the beach’s beloved Wreck Bar.

Join throngs of locals on the five-minute ferry ride across Victoria Harbour between the Tsim Sha Tsui cruise pier in Kowloon, on the mainland side, and the Central Pier on Hong Kong Island (a slightly longer ride goes to Wan Chai on Hong Kong Island). This is not just any ferry: The historic green and white Star Ferries have been moving the masses back and forth for decades, with the origins of the company going back to 1880 with the service of a single steamboat, the Morning Star. Today, the classic wooden boats make the trip many times daily, and a ride provides a great view of the city’s famous skyline and a whiff of nostalgia to boot.

No visit to Antigua is complete without taking in the sunset atop Shirley Heights Lookout at its weekly Sunday sundowner party. The view from Shirley Heights is without a doubt the most famous, most photographed, most celebrated vista gracing Antigua. Immediately below, English and Falmouth Harbours clutch their bays. On clear days you can see Guadeloupe to the south and Montserrat with it’s still active volcano to the south west. It does get busy, so expect a crowd and while there might be a couple locals sprinkled in here and there, it’s mostly visitors. Around 7ish, the tunes crank up with either some reggae classics, some pumping soca, or even live a steelpan band. Smoke from a collection of barbecues compete with the music to fill the air and stimulate your senses. Expect chicken and ribs slathered in local flavors, plus burgers for the less adventurous. I did have some trouble getting grilled fish on my last visit, but once I found some, it was charred to perfection.

One of my favorite discoveries in Chicago is the Empire Ballroom inside The Palmer House. It’s just up the stairs from the hotel’s magnificent lobby and has a rich history most anyone working at the hotel will be willing to tell you more about. This room with its shiny wood floor and opulent chandeliers is where Frank Sinatra used to perform. While the ballroom itself is beautiful, it’s most interesting feature is what’s hidden behind the mirrored wall in its corner. Push on the last panel and you’ll stumble into a dressing room where famous acts - including Sinatra - used to get ready to go on stage. Several autographed pictures are still hanging on the walls.

The story behind the founding of the Museo del Juguete Antiguo México (Museum of the Antique Mexican Toy) is almost as charming and intriguing as the collection of toys itself. Roberto Shimizu, Sr., who founded the museum with his son, Roberto Shimizu, Jr., began collecting toys when he was a child and in the decades since, has amassed a collection of literally millions of toys. He decided it was important for the collection to be accessible and visible to the public, partly to document the history of toy-making in Mexico and the world. The space occupied by the museum covers several floors, but it’s barely large enough to showcase all of Shimizu’s treasures, which he has catalogued carefully in numerous notebooks and binders. That may be hard to believe, given the fact that the museum is crammed wall-to-wall and floor-to-ceiling with toys of every type: from plastic soldiers to board games and Barbies to model trains. The museum is a cabinet of curiosities for the kid in all of us.

Are you kidding me? 150 feet deep AND the opening to miles of underground caverns? And you want me to jump in? If it isn’t the 30 foot drop that gets you, its the inky blackness below or the who-knows-what that’s living down there. You see, the rainbows that shimmer in the water- falls, and the roots and vines that hang like some bridal veil, and the sunlight that flickers about the place are all just trying to pull you in--into the black nothing that lurks beneath. Never-the-less, if you are brave enough to take the plunge, you will be rewarded with velvety sweet water that feels like lotion on your skin and baby catfish that tickle your toes and, best of all, the exhilaration of knowing you swam in the very entrance to Xibalba, the Mayan underworld. So descend into the cavern and climb the chiseled staircase to the dive platform and make sure when you jump, you hold your breath, cause its a long way down.

The Santa Monica Pier embodies what Southern California is all about: fun in the sun. Popular with tourists and locals alike, this iconic boardwalk adjacent to the Pacific Ocean—filled with all the amusement rides, midway games, fried food, ice cream and cotton candy you can dream up—is a fantastic place to spend a nice day. My favorite attractions are the Santa Monica Pier Aquarium and the world’s first solar-paneled Ferris wheel, which provides breathtaking beach and ocean views as you ride ‘round and ‘round. Be sure to dip your toes in the soft Santa Monica sand, too. Nearby, you’ll find the Third Street Promenade, a bustling entertainment district filled with wonderful eateries and shops.

Once a separate municipality, San Ángel—in the city’s south, nestled into its western foothills—is a leafy, genteel enclave whose relative isolation adds a soigné feel (for better or worse) you won’t find in neighboring Coyoacán. Ground zero for promenading is quaint Plaza San Jacinto, whose cute parish church (and beautiful cloister garden) is a sort of spiritual last stand amid the surrounding area’s high-toned consumerism. That said, the plaza’s true spirit comes alive Saturdays, at the so-called Bazar Sábado, an artisanal market that fills the area with stall after stall of handmade jewelry, textiles, crafts, and accessories, plus a great deal of art—some finer, some less so—in styles that go from hippie to haute. Strolling musicians and performers add to the carnival atmosphere.

Row after row of booths are sprawled across this small part of Shanghai, just south of People’s Square. Here, you can find pretty much anything you want, from tiny Mao statues, to old leather suitcases stacked 10 feet tall. Each vendor will be on you as soon as you approach their booth. They are quite polite, however, and will have a calculator or phone handy to show you the price for their items. The catch is that the majority of these “antiques” are actually factory-made items, and most booths have similar items. The good part is that you have a really good chance of a low price if you bounce back & forth between booths that have the same items. Shopping aside, this is also a great spot to see daily Shanghai life. Laundry hangs over your head, food trucks cruise up and down the rows, and the vendors socialize with each other when they are not selling items. This is a must for any visitor to Shanghai.

Over the past two centuries, the covered market at Borough, not far from London Bridge, has become one of the country’s most famous foodie spots. From Wednesday to Saturday each week hundreds of traders gather to sell homemade breads, hand-reared pork, artisan chocolate and all manner of ingredients—plus excellent coffee, fresh juices and organic wine. Plentiful samples add to the convivial vibe, and restaurants around the market’s edge provide additional sustenance for longer stops.

Standing its ground between a cypress grove and the Pacific Ocean, the Point Pinos Lighthouse is the oldest lighthouse in continuous operation on the U.S. West Coast—and one of seven lighthouses for which Congress appropriated funding shortly after California statehood was ratified. But this lighthouse wasn’t just an aid to navigation; it was also a social hub in early Pacific Grove. Robert Louis Stevenson wrote about lighthouse keeper Allen Luce and his piano playing, while a fondness for entertaining inspired locals to call keeper Emily Fish the Socialite Keeper. The lighthouse beacon, a third-order Fresnel lens, has flashed nightly since 1855 and is still used in the tower today—the light is visible up to 17 nautical miles out to sea. Docents are on duty to answer questions as you tour the lighthouse, from the 1890s-style parlor to the 1920s-style kitchen, and up to the Emily Fish bedroom and lookout. Right behind the lighthouse is the El Carmelo Cemetery, one of the most peaceful seaside cemeteries, with deer wandering through to nibble on the grass.

Downshift on this groovy Gulf Island, just a 35-minute seaplane ride from the city. Here, artist studios abound, as do makers of artisanal food and beverages. Classic stops include the summertime Saturday Market, the Blue Horse Folk Art Gallery, and the farmstead tasting room at Salt Spring Island Cheese. Hikers can get their fix at Ruckle, a lovely provincial park with 4.3 miles of coves, tide pools, and rocky headlands, while scuba divers can drift offshore, admiring octopuses and lacy fields of plumose anemones. No car? No problem. The islands have a designated hitchhiking program; just wait for a pickup at the “Car Stop” signs.

Lotus Garden Cottages is an adorable boutique escape set among the rain forest of Volcano Village near to Hawaii Volcanoes National Park. The four luxury rooms—two cottages, two suites—are furnished in warm wood and each comes with a lanai, small kitchen, and TV equipped with Roku box. The rooms are decorated with artifacts taken from Korean temples, and this Zen vibe extends to the grounds, too, with a peaceful meditation garden, koi pond, and outdoor hot tub. Breakfast includes the most exquisitely plated fruit you have ever seen, served in your room by the proprietor, John. If you’re lucky, you’ll hear him playing violin in the office while you bask in a tranquility that is all the more remarkable given the restless fury of the nearby volcanoes.

Healthy, organic food can be difficult to come by in Gatlinburg, making this natural food store and café a staple for locals and travelers seeking a nourishing or vegetarian-friendly option. Burgers come in the form of ground salmon or lentils (in a sprouted grain bun), washed down with the fresh-pressed juice of the day or a “wellness shot” of wheatgrass, ginger, or turmeric. Built in a rustic stone-and-wood cabin, the café is small but cozy, and during summer, the exterior is cheered by blooming daisies and echinacea. There’s also a well-stocked herb and vitamin section, plus plenty of seasonal, organic produce and groceries to pack a picnic or stock the pantry.

Though a relatively new option for tourists, the Crystal Caves of Grand Cayman’s Old Man Bay have been hosting other sorts of visitors since time immemorial: Everyone from bats (who still hang out near the entrance) to farmers (in search of the attendant guano) to pirates (where better to dodge both hurricanes and the law?). Shrouded within a healthy radius of rain forest, these stalactite-and-stalagmite-studded caverns are well worth your visit, too; whether or not you locate the treasure that some of the previous occupants are rumored to have left behind, you’ll find a wealth of natural beauty—especially the reflection of all those formations in the gin-clear rainwater lake.