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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.

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.

At the center of Medellín, Plaza Botero gets its name from Colombian artist Fernando Botero, who donated 23 of his much-loved, disproportionate-bodied bronze sculptures to the city. There’s a huge chubby head, a reclining woman, and an oddly small man with a bowler hat riding a horse, plus good old Adam and Eve. The Museo de Antioquia abuts the plaza and houses other pieces by Botero as well as works by other artists. By day the square is vibrant and lively, but do take appropriate precautions after dark.

One of the most popular atolls to visit, Arno is reachable by a 45-minute boat ride from Majuro. It offers white-sand beaches and waters with plenty of marine life—including sharks. There’s a simple cabin to rent for overnight stays and a tiny snack shop (it’s a good idea to bring your own food and water, as well as mosquito repellent). If you’re lucky (or ask nicely), the friendly locals may make you some coconut crab.

Bordered on the south by its eponymous deep-red cliffs, the national monument is home to broad plateaus, endangered California condors, and some of the oldest petroglyphs in the United States. But the area’s greatest hit is the Wave, a dramatic, undulant orange rock formation. There are trailheads, maps, and minimally marked checkpoints along the trail leading to the famous spot, but unless you opt to hire an authorized guide, you’ll have to pick your way carefully across relatively untouched desert—that is, if you manage to snag one of the 20 daily hiking permits. Apply online four months in advance or enter the daily lottery at the visitor center in Kenab, Utah. Didn’t make it? Grab a map, make sure you have a spare tire, and explore the monument’s lesser-known slot canyons and gulches, or head to the Grand Canyon or Zion National Park; both are within a two-to-three-hour drive. You can always try again the next day. Permits are $6 and $7.

Long considered one of the top hotels on Oahu, the Kahala has always been a particular favorite among the type of guests who travel with their own security detail. A number of past U.S. presidents, plus kings, queens, princesses Grace and Di, a handful of Nobel Peace Prize winners, rock stars, and movie stars, all have slept under its venerable roof at some point during the hotel’s 50-year history. The see-and-be-seen set moved on long ago, but privacy seekers still make a beeline here. They’re drawn less by the property’s fabulous beach (though that’s reason enough to stay here) than by its exclusive location—in a well-fortified cul-de-sac in the ritzy Kahala neighborhood. But there’s a warm and fuzzy side to the hotel, too. A pod of dolphins has full-time residency in the hotel lagoon, and visitors of all ages can swim with them (for a fairly steep fee). Rooms have a preppy beach house vibe—raffia ceiling fans, linen loveseats—and many come with heart-stopping sea views.

With the smallest room a sprawling 400 square feet, and suites and public spaces filled with original 18th- and 19th-century art and antiques, the George V, flagship of the Four Seasons chain, lives up to its billing as a palace, an official tourism category introduced in 2010 requiring establishments to “embody French standards of excellence and contribute to enhancing the image of France throughout the world.” Set in a 1928 art deco building, the Four Seasons Hotel George V boasts a regular clientele of bona fide royals, including Saudi princes who rent entire floors for six weeks at a stretch. The staff includes a team of flower designers led by an art director who worked on Chelsea Clinton’s wedding. There’s also a dedicated concierge for children ordering up pint-sized bathrobes and private pastry-making lessons in the Michelin-starred kitchen.

Sure, you can fly straight into Zanzibar, but where’s the fun in that? The Azam Marine ferry makes for a wonderful adventure from Dar es Salaam to Zanzibar, departing from the port in Tanzania’s capital four times a day. Passengers can sit out on deck as the catamaran edges away from the mainland, taking in the sea breeze, admiring the quaint little fishing boats bobbing about in the sunshine, and watching giant trawlers heading out into the glistening sea. The VIP experience is the way to go—VIP passengers are treated to reclining red-leather seats and a free coffee during the 90-minute journey. Suffer from seasickness? Beware: The water can be choppy in the afternoon, so opt for an early sailing instead. Advance booking is necessary.

Rock ’n’ Bowl is where to go to find sharps, flats, spares, and strikes all hanging out together. It’s a bit unclear whether this is a nightclub hiding out in a full-size bowling alley, or a bowling alley out enjoying a secret nightlife. Either way, it’s a very New Orleans destination, located near the upriver edge of the city. (It’s about a $15 cab ride from downtown.) After Katrina and a parting of the ways with his earlier landlord, the owner moved a few blocks down to this former paint store, installed new lanes, added a bigger stage, and hauled much of his original funky decor to the new spot. Check the website for forthcoming shows—there’s always plenty of space for dancing, which is especially fun during Thursday zydeco nights.

Mandarin Oriental’s first Caribbean resort has all the amenities you’d expect from the luxury brand—with the price tag to match. Nestled within lush greenery overlooking the white sands of Godahl Beach, the 26 suites and villas, which sit on the grounds of a 1,200-acre estate on the island of Canouan, are elegantly appointed with modern furnishings, marble baths, and rosy accents befitting the hotel’s name. Here, though, it’s all about the public spaces, including a Jim Fazio–designed golf course overlooking sparkling blue waters, a hilltop spa specializing in island-themed treatments, and four elegant restaurants serving every kind of cuisine, from pan-Asian to Italian. At Turtles, a cocktail lounge straight out of the Hamptons, opt for the Pepper Bliss, made with rum, bell pepper syrup, and pineapple juice.

The past two decades have seen the dozens of islands scattered across Boston Harbor transformed from barely noticed dots on the horizon to one of the city’s most popular attractions. The Boston Harbor Island National Recreation Area, established in 1996, has propelled them into prominence, with ferries carrying day-trippers and overnight campers from downtown Boston, Hingham, and Hull to eight of the islands (19 more are accessible by private boat or charter excursions). Most visitors head to Georges Island, home of the Civil War–era Fort Warren, or the beaches and hiking trails of Spectacle Island, the one closest to downtown Boston. (Don’t skip the concession stands here: The food is from James Beard Award–winning Boston chef Barbara Lynch.) You can also camp on Peddocks, Grape, and Bumpkin islands, or take a tour to Little Brewster Island to witness the 300-year-old Boston Light, the nation’s oldest lighthouse.

It would be hard to find a more idyllic spot for recharging than Naïa Resort and Spa, Placencia’s newest (and, we’ll say it, most comfortable) resort. Stay in your own studio, one-, two-, or three-bedroom beach house, all of which come equipped with floor-to-ceiling front windows, a kitchenette, a deep tub, and an outdoor shower (trust us: once you’ve had the luxury of an outdoor shower, you’ll never want to go back to the boring, indoor version). Every beach house is just that: a beach house. You’re never more than a short walk from the shores of the Caribbean Sea, and the Naîa’s watersports center can get you off the sand and into the water on a kayak or paddleboard. (While you’re there, ask for Stony, whose a pleasant man to talk to and the guy you’ll need to open a fresh coconut from one of the many palm trees on the property). The resort also staffs expert concierges, who can recommend the best tours, spa treatments, and in-town experiences.

The spa, as expected, is one of Naïa’s best features. Located a short golf cart drive away from the lobby, Naïa’s spa feels like a secluded oasis. Lillypads sit calmly on the surface of still ponds, and treatment rooms—all housed in small, individual wooden buildings—overlook the vegetation. The masseuses will alleviate you of all pent up stress with expert hands and sweet-smelling lotions exclusive to the resort.

The town of Placencia is only a short drive away, and the Naïa can shuttle you wherever you need to go. Eat and drink at Barefoot Bar or Tipsy Tuna, walk along the paths near the beach to find handmade treasures to take home, and hang out by the docks and watch the fishing boats come and go. Then go back to your little slice of paradise on the Caribbean shores.

One of the hippest neighborhoods in the city is Amsterdam-Noord, situated directly across the IJ River from the main train station. Here, an iconic 1970s office high-rise has been recently revamped and rebranded as A’DAM, an acronym for Amsterdam Dance and Music. Along with music-themed businesses, restaurants, and an underground nightclub, the tower boasts the rooftop Lookout, an open-air observation deck 20 stories up that offers panoramic views of the historic city center, the bustling port to the west, and the Dutch landscape beyond. Daredevils line up for Over the Edge, a huge metal contraption that lets you literally swing out over the edge of the building. Entrance to the Lookout is €12.50 (about $15) and a ride on the swing is €5 (about $6).

One of the few hotels on picture-perfect Grace Bay Beach that can work for both honeymooners and families, Seven Stars sits on 22 acres of lush grounds at the edge of Princess Alexandria National Park and has studio to four-bedroom plantation style suites available. All feel very private. Besides wraparound terraces with awesome ocean views, the rooms here all feature full kitchens, making it easy to cook your own lunch or make snacks for the kids. That said, the house restaurant, aptly named Seven, is very good, so plan on dining here at least a few times. The spa is also excellent - perfect for honeymooners - and there is a dedicated activities concierge that will arrange all sorts of water sports and even a kids’ camp.

You will likely see Bronzino’s famous portrait of Eleonora (or Eleanor) de Toledo, in the Uffizi, during your visit to Florence. The Spanish noblewoman who became the duchess of Florence in 1539 when she married Cosimo I de’ Medici was unusual for her time, playing an active role in politics and as a patron of the arts. Her patronage extended to garden design, in its infancy (at least in Europe) in the 16th century. Eleonora commissioned the Boboli Gardens behind the Pitti Palace as a green escape from the city; they continue to provide a retreat for travelers today.

Among the earliest examples of the formal compositions that would dominate garden design through the 20th century, the grounds are dotted with classical statues and fountains while straight axes run up and down the hillside with an apparent disregard for topography. A moment in design history can be experienced first hand here. There’s a feeling that the man who planned the gardens (Niccolò Tribolo) conceived a formal plan and then simply laid it atop the site. Principles of garden design were later to shape city planning. The allées of the Boboli Gardens were early models for grand boulevards leading the eye to distant monuments. One of the pleasures of gardens, however, is that you don’t need to know their histories to enjoy the flowers in bloom or the sounds of birdsong and splashing fountains.