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Given the civilized associations of the Côte d’Azur, the Massif des Maures may come as a surprise. This small mountain range that runs parallel to the French Riviera for some 60 kilometers (36 miles) is still, at least in areas, decidedly wild with its typically Mediterranean forests of oaks, pines and chestnut trees. Don’t expect the soaring peaks of the Alps—even the tallest mountains are under 750 meters (2,460 feet)—but on the plus side, that makes the area accessible even for casual day hikers. Well-marked and maintained trails lead to a more rugged Provence that feels far from the beach towns below. (Note, however, that some routes may close in the summer and autumn depending on the risk of fire.)

The Carbet Falls (Les Chutes du Carbet, in French) is one of Guadeloupe’s most famous sights, a series of three waterfalls tumbling down the side of the volcano La Soufrière, with a backdrop of lush Parc National de Guadeloupe foliage. The first falls drops 125 meters (410 feet), the second, 110 meters (360 feet), and while the third has the greatest volume of water, it’s the shortest, at only 20 meters (66 feet). The second falls is the most visited, largely because it’s an easy 20-minute stroll from the parking lots. Visiting the first falls involves a hike up a steep trail that’s just under a kilometer (3,000 feet). Only experienced hikers should attempt to visit the third falls.

The name translates as “Back Pocket,” an apt description for this one-room restaurant tucked into the side of the Royal Opera House. The tiled room is decorated with opera memorabilia, and sometimes you’ll find yourself dining next to tuxedo-clad members of the orchestra between performances. Diners perch at the counter at little tables affixed to the walls or, during the summer, outside in the sun. The food is traditional Swedish cuisine—husmanskost, as it’s known—with particularly good seafood, and best enjoyed with a Swedish beer.

Ramble down this scenic Punda road, and you’ll soon encounter two of the island’s most renowned art galleries. Serena Art Shop is famous for its handpainted Curaçao Chichi figure, while visitors can’t get enough of the Nena Sanchez Gallery’s striking island-themed paintings and giclées (prints). On the next street over, SilvanyRoss, a charming shop, features one-of-a-kind souvenirs sourced from local entrepreneurs and artists, from wood-carved coasters to oil paintings and handmade purses. Get to Windstraat on the early side; most of its stores and galleries close up by 5 p.m.

It may be only 22 miles west of San Juan, but Dorado Beach, a Ritz-Carlton Reserve feels a world away. The resort has a spectacular location on a three-mile stretch of beach on Puerto Rico’s north shore, where Clara Livingston once ran a sugar plantation—and Amelia Earhart visited before departing for her fateful world tour. In 1958, Livingston sold the property to Laurance S. Rockefeller, who turned it into the first of his legendary Rock Resorts. Known for his green streak, he designed the hotel to respect the local beauty, mandating that buildings could not be taller than the surrounding palm trees.

The Ritz-Carlton—which reopened in October 2018 after a meticulous restoration following Hurricane Maria—pays homage to that original vision. Here, every room is beachfront, with floor-to-ceiling sliding doors that disappear into ocean views, plus deep soaking tubs, outdoor showers shaded by gardens, and either spacious balconies or private plunge pools. As part of the property’s renovation, rooms were refreshed with a color palette that amplifies the natural beauty just beyond the doors. Additionally, the grounds showcase 3,000 new plant species, the spa is offering new locally inspired treatments and cuisine, Encanto Beach Club Bar & Grill features a refreshed dinner menu, and the Positivo Sandbar debuted an omakase and ceviche bar directly on the sand. There’s even an entirely reimagined signature restaurant, Coa, which serves farm-to-table fare cooked on the grill. Still standing strong on the verdant, 1,400-acre grounds are the five 18-hole championship golf courses. The biggest challenge is pulling yourself away from the luxury of the resort to tee up a shot.

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.)

This refined 28-acre resort set in the rolling hills between downtown Sonoma and downtown Napa makes guests feel relaxed the moment they check in. The vistas are unobstructed from the resort’s pool areas, and many of the property’s 94 stand-alone cottages with private balconies and six private homes offer views of the open space, too. By day, lawn games are usually underway on the grassy expanse called the Town Square, while in the evenings, a pavilion provides an unparalleled backdrop for stargazing. This is a hotel that values fresh air, as evidenced by the walls in the common areas, which retract to bring the outdoors in. There are other reasons to fall in love with Carneros—namely, the on-site restaurants. The casual Boon Fly Café is famous for breakfasts, with spicy bacon Bloody Mary drinks and tiny made-to-order doughnuts. FARM, on the other hand, is more formal, with menu items such as braised oxtail terrine and smoked Sonoma duck breast. While the hotel offers in-room massages, it will also reopen its spa after a full-scale renovation later in 2018.

Right by the Pile Gate, in a beautifully restored maritime school, Restaurant Nautika feels special even before you taste the food. With mesmerizing views of Kolorina Bay beyond and Lovrijenac Fortress looming overhead, this elegant restaurant has a fresh spark about it. The chef often does the marketing himself, browsing the stalls at the local market for organic and locally grown produce and freshly caught seafood—the only ingredients used at Nautika. The kitchen works magic with the ultra-local stuff, turning out small wonders like lobster medallions and sesame-crusted tuna. The inspired cuisine, especiailly when coupled with the location make the Nautika experience nothing short of spectacular. (If the view isn’t enough, you can occasionally spot celebrities among your fellow diners.)

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 bars along 5th Avenue start hopping as early as sunset, but Calle 12 doesn’t pick up until well after dark. Pronounced kah-yeh doh-say, the lane is Ground Zero for Playa del Carmen’s wilder nightlife, with nightclubs and bars on both sides of the street between 10th and 1st avenues. The hottest venue depends on when you go—which night, week, or even season—but the most popular spots include Coco Bongo, La Vaquita, Coco Maya Beach Bar, and Mandala. (Note: Things don’t start till 11 p.m. at the earliest on Friday and Saturday nights.)

Day and night, dumplings are being made by hand, boiled and fried at the original branch of Mr. Shi’s in Baochao Hutong and at the Sanlitun outpost. This is not your corner dumpling joint but a cleaned-up space where the menus are in English and the menu overflows with more than 50 varieties of dumplings. There are the traditional—think pork and chive or leek and egg—and there are the unusual, such as pizza (cheese and tomato). While you can certainly live on dumplings alone, Mr. Shi’s has solid sides, including sliced cold cucumbers with garlic (a treat on hot summer days), a nice tofu salad, and stir-fried egg and tomato, a home-style classic that’s also available in dumpling form.

Barbados is considered the most British of the West Indies, and its historic churches, which wouldn’t be out of place in an English village, help it claim that title. On the site of older churches that were destroyed by fire and hurricanes, some dating as far back as the 17th century, St. John’s Parish Church is an early-1800s dark stone Gothic gem. Though the earliest St. John’s church was constructed in 1645, the one that stands today is largely from 1836, replacing a building destroyed by a hurricane in 1831. Its remarkable pulpit is made of ebony, mahogany, locust and other local woods. Many prominent figures are buried in the graveyard, which has views of the coast.

Conquistadors built Panamá Viejo, the first European settlement on the Pacific Coast of the New World, in 1519. The original site was abandoned in 1671 after Henry Morgan’s pirates attacked and the residents relocated down the coast. This second settlement, now called Casco Viejo (old town), is the historic district of Panama City. Together, both locations make up a UNESCO World Heritage Site. At Panamá Viejo, visitors can explore an archaeological site with famous ruins, while Casco Viejo is abuzz with the markets, cafés and nightlife found along its narrow streets and in its classic waterfront buildings.

The quiet street known as Avenida Nader, where several pioneers lived during the city’s 1970s genesis, ranks among the most “historic” neighborhoods in this all-but-brand-new city. With City Hall’s rear garden to the west and an upscale neighborhood of winding streets to the east, the avenue has transformed in recent years, going from quaint and residential to an eclectic mix of hipster bars, lantern-lit outdoor restaurants, and hidden street art. The strip embraces its historic roots while also providing a bit of vie de bohème you might not expect at a beach resort.

Ponce is Puerto Rico’s second-largest city and is nicknamed the “Pearl of the South.” Life here seems to move at a slower pace than San Juan, and that’s the way locals like it. For them, there’s nothing better than an evening or weekend stroll around Plaza Las Delicias, the main square, which is full of history and entertainment. Stop by the unmissable red-and-black–wooden firehouse (now a museum) to learn more about the central roles that fire and firefighting have played in Ponce’s history. Then work your way around the square to see Ponce’s symbol, the lion, anchoring each side of the plaza, the church, the fountains, and finally, Kings Cream, a no-frills emporium that sells small cups of ice cream—with flavors such as passion fruit, peanut, guava, and coconut—at bargain prices.