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In the heart of El Viejo San Juan, the Plaza Colón (Columbus Plaza) is so much more than a place honoring an important piece of San Juan’s history. Sure, snapping an Instagram photo in front of the bronze statue of Christopher Columbus, credited for the first discovery of the island, is definitely a “must-do.” Find a local and in your best Spanish accent say “Perdón, podría tomar una foto por favor?” Or play it safe and ask another tourist in English (they’re not hard to find!). Either way, stay and hang out. Explore the local artists’ tents (like this one, with rings and bracelets made from brightly colored ceramic beads and recycled aluminum, customized to fit). Pick out unique, inexpensive gifts for loved ones and, of course, something to remember the trip! And don’t ignore the ringing bell of the sorbet vendors selling “coco frio” for $1. Try a scoop of papaya y piña to help cool off in the heat of the Puerto Rican sun.

Located in East End Village and painted in Anguillan flag colors, the Heritage Collection is Anguilla’s only museum. It showcases the island’s history and geology from the time of the Arawaks to the 1969 Anguillan revolution, with additional displays on the British invasion (derisively called the “Bay of Piglets” by the press) as well as on Queen Elizabeth II’s royal visit. Established in 1996, its collection includes photographs and artifacts from the island’s major eras, including the days of slavery and the phosphate trade. If you’re lucky you’ll meet Colville Petty, the museum curator and founder, and garner some of his unique insight on Anguillan history.

Cherry Hill Historic House and Farm at 321 Park Avenue is a social center and a tourist draw. Built in 1845, it was once a thriving 73-acre farm owned by William A. Blaisdell and was occupied during the Civil War. Today, it is owned by the City of Falls Church and operates as a museum showcasing 18th and 19th-century furniture and tools, a buggy shed, a tackle barn, a corn crib, a well-house, and “necessary” (outdoor toilet). Guided tours are offered Monday-Thursday from 10 a.m. to 3 p.m. and Saturdays (April-October) from 10 a.m. to 1 p.m. In addition, events and public programs such as afternoon teas, concerts, children’s activities, workshops, weddings, and receptions occur year round.

Thrifters, costume lovers, and antique collectors can all find something to love at Junkee Clothing Exchange, one of Reno’s most charming vintage stores. You can bring your clothes to sell for store credit, or simply wander among the racks of sequined dresses, costume accessories, vintage boots, and fur coats. Don’t forget to admire the creepy-cool goth-circus artwork hanging on the walls, and the elaborate chandeliers. The other half of the store is a large antique mall with individual stalls run by separate sellers. You’ll find everything from vintage rhinestone jewelry to garden-party hats and World’s Fair souvenirs. Prices are reasonable and they carry clothing for men and women in a wide range of sizes.

Upstairs from her flagship Delirio boutique (also worth a duck-in), a beautiful town house is home to chef Mónica Patiño’s Casa Virginia, featuring a changing seasonal menu that takes creative advantage of Mexico’s wide-ranging culinary variety. Its sunny dining room and nostalgic “shabby chic” details cannot fail to delight; its family-style servings are great for sharing. Recent specials included an endive salad and two artichoke preparations, a squash soup, a Mexican-style osso buco, and a rack of lamb. All ingredients are locally sourced and most of the herbs—a key element in everything Patiño does—are grown on the roof. There can be few more civilized meals anywhere in Mexico City.

Superlatives reign at this massive Palm Beach resort. Among the outsize offerings? The biggest casino in Aruba, with more than 500 slot machines and 26 gaming tables, as well as the island’s largest spa. Its 414 accommodations aren’t lacking for space either: Each room has a walk-in closet, double-sink bathroom, and private balcony; the highest-end suites are so palatial their balconies alone measure up to a sprawling 500 square feet—with ocean views to sweeten the deal. When you’re not playing roulette or indulging in a moisturizing coconut-milk wrap, kick back in one of the beachside palapas, or practice your breaststroke in the free-form pool, complete with cascading waterfalls and a volleyball net (a serene adults-only pool features a swim-up bar if that’s more your speed). In keeping with the more-is-more theme, guests are spoiled for choice with seven on-site restaurants, bars, and cafés, including a Ruth’s Chris Steak House, where the 500-degree plates ensure another best—the hottest meal in town.

Yo, ho, ho and oh, my! Up on Government Hill, this watchtower, built circa 1678, is known as Blackbeard’s Castle and is literally the stuff of legends. Although it’s open for debate whether the notorious pirate ever used the five-story tower as a lookout, one thing is for certain: Its views are tops. Nearby the flower-lined 99 Steps (technically there are 103), built in the 18th century of ship-ballast brick, lead from historic Kongens Quarter to some more terrific views of the island.

Crashing waves serve as the soundtrack to your stay at Elbow Beach, situated on 50 lush acres along Bermuda’s rose-hued southern coast. Decorated with exposed beams, tiled floors, and neutral color schemes, the spacious cottage-style rooms are the portrait of coastal elegance—think coral-emblazoned throw pillows, wicker benches at the foot of the beds, and ocean or garden views through French doors. Polished-pebble paths lead the way to the spa, which offers treatments inspired by local ingredients, from a ginger-and-coconut scrub to a hibiscus bath. Grab a rum swizzle in the lounge, relax by the curving perimeter of the pool, or snorkel, swim, and kayak at the hotel’s private beach. You might also prefer to hit the pavement: Elbow Beach is mere minutes from the capital of Hamilton, Gibb’s Hill Lighthouse, and four 18-hole championship golf courses.

Perched high above the sea on the east coast of St. Kitts is Brimstone Hill, a massive stone fortress built by African slaves for the British during the 17th and 18th centuries. Now a UNESCO World Heritage Site, the military stronghold, which took 100 years to complete, is considered one of the best-preserved fortifications in the region. From the top, you can see six neighboring islands on a clear day.

In April 2017, the World’s 50 Best Restaurants List (produced by the British magazine Restaurant) bestowed the title of the greatest restaurant anywhere on Eleven Madison Park. It marked the first time in 13 years that an American establishment secured the top spot. (The previous U.S. winner was Thomas Keller’s French Laundry, in 2003 and 2004.) It’s not the restaurant’s only laurel: It has also received three stars from Michelin and four from the New York Times. If you want to judge for yourself, be prepared to spend $295 for an 8-to-10-course tasting menu (or $155 for the smaller five-course bar menu). Both prices include tips, but not beverages. Executive chef Daniel Humm’s menu could be called haute American—local ingredients are highlighted in dishes with preparations that border on, but don’t cross into, the fussy. The dining room itself complements the meal. Right after the restaurant was named the world’s best, it closed for a four-month renovation, and its new light- and art-filled interior pairs perfectly with Humm’s dishes.

Almost unchanged since 1912, the Théâtre Corona (Corona Theatre) in Little Burgundy was built to host showings of silent films accompanied by live music and comedy shows by local troupes. You can still find an orchestra pit and the original dressing rooms under the stage, but since the late 1990s—after coming close to demolition—it has served mainly to host live music, by acts like Buck65, La Roux, and Arcade Fire. The heritage décor, with painted ceiling, gilded columns and heavy jacquard brocade curtains, and the relatively small capacity for 700 spectators, make this a singularly intimate place to see a show. The best sightlines are from the balcony, but there’s nothing like the feel of a smooth wooden dance floor beneath your soles.

Boat-building as an industry has existed on Bequia as far back as the 1800s. At one point, the island was even known as the “boat-building capital of the West Indies,” having produced the largest wooden vessel in the region. While construction has slowed over time, it still occurs—albeit on a much smaller scale—at places like Sargeant Brothers Model Boat Shop, just up the road from the ferry landing in Port Elizabeth, where Benson Phillips and other craftsmen make and sell their models. Handcrafted using hand planes, chisels, and carving knives, their boats are incredibly detailed and realistic. Choose from whale boats, sailboats, power boats, and wooden schooners, or commission Phillips to build a custom model of your own yacht. The simplest models take about a week to make, but there are always a few boats available for immediate sale, ranging in price from around $250 all the way up to $7,000.

Nothing says Santorini like an aqua-blue infinity pool, and Katikies has three of them—all the better to take in westward-facing sunset views. Carved out of the cliff side 300 feet above the Aegean, the hotel’s public spaces are connected by a series of bridges and Escher-esque stairways as they descend from the town of Oia above it. Cube-shaped rooms and suites are minimalist but inviting, nearly every surface painted or clothed in calming white; all have verandas, while a few large suites have outdoor plunge pools or Jacuzzi tubs and alfresco seating areas. Upon check-in, guests are given cell phones to summon 24/7 service from anywhere on the property. They use them to order light snacks at the poolside bar and restaurant or make reservations for some of the best sushi on the island at the champagne bar, but the candlelit rooftop restaurant—serving Greek and Anatolian cuisine—is about as romantic as it gets.

Getting to Onar Andros requires a fair amount of determination. A ferry from Athens or Mykonos takes you to one of the northernmost Cycladic islands (there’s no airport nearby); once you arrive at the port in Gavrio, it’s a slow 25-mile drive to the hotel. Your reward, however, is a tiny slice of Eden, an enclave of 10 stone-and-timber cottages set amid a lush river valley that’s only a five-minute walk to Ahia Beach, arguably the most beautiful in all the Cyclades. Built and maintained by the owner, Mateo, the accommodations are deliberately spare yet modern and comfortable, each with a pergola-shaded veranda with loungers and a hammock. Meals are served at a communal table, and what Mateo doesn’t grow organically, he sources from local fisherman, farmers, and bakers. Guests can even accompany him to pick fruits and vegetables to be used in that night’s dinner. After all, this is a place to ditch your devices and surrender to your surroundings.

In 2012, one of the world’s richest men—Oracle founder Larry Ellison—bought 97 percent of the island of Lanai. The single sweeping deal (reputed to cost $300 million) included the exquisite Four Seasons Resort, overlooking a marine reserve. The resort’s dining experience par excellence is Nobu, where celebrity chef Nobuyuki Matsuhisa presides over the perfect marriage of Japanese dishes and Peruvian ingredients. Kick things off with crispy Brussels sprouts or scallops with jalapeño salsa, then move on to sushi, hand rolls, or Wagyu beef. Save room for the Bento Box dessert with green tea ice cream and chocolate flourless cake. Or go old-school, if it’s on the menu, and order the mochi pound cake backed by yuzu-cherry jelly and peanut butter ice cream.