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Spectacular hilltop villages are a dime a dozen on the Greek islands, but Astypalea, a distant speck in the Dodecanese, has the quintessential sugar-cube capital cascading over a rocky outcrop to a sheltered harbor. The oldest houses are huddled along the cliffs circling the Venetian Querini Castle. Castro Bar is built right into the 15th-century castle walls (which look even more dramatic when illuminated by moonlight). A series of small terraces on different levels, painted in white, burgundy, and blue, all offer stupendous views across the island and what feels like the whole Aegean. The vibe is mellow, and the drinks are strong. Stay until the sun rises out of the sea, a trippy experience you won’t forget.

Once the center of commerce in Charleston, the City Market is now the heart of tourism. Although its location near the cruise terminal can make it feel like a kitschy open-air market in the Caribbean, the tackiness is part of its charm. Yes, you’ll find Christmas ornaments painted with Rainbow Row and enough cutely packaged pralines to give you a stomachache, but you’ll also see Gullah artisans weaving the finest examples of sweetgrass baskets available. Peak season brings 140 different merchants, and weekends include live music and food vendors. The market’s a requisite stop for any visitor and a one-stop gift shop for loved ones back home.

In the increasingly gentrifying El Raval neighborhood, along the leafy main avenue of Rambla del Raval, a whole host of restaurants, cafés, and bars are popping up. Among them is this intimate bistro from noted Catalan chef Carles Abellán, which takes a refined approach to traditional home cooking without being pretentious. To that end, the narrow dual-level space, a former bodega, is simply decorated with rustic wood furniture, forest-green walls, and a ceramic-tiled, marble-topped bar. The menu is divided into categories of small dishes—From the Sea, From the Mountain, From the Orchard—plus a few versions of classic Spanish stews. Leave room for the homemade desserts: The soft, silky Brie cheesecake is divine. Reservations are essential.

Book a sunset charter on Atebeyra, a boat that comes with a rum-running history (she ran booze during prohibition) for a unique evening excursion. The boat can also be chartered for day trips to the outer islands where you can spend the day lazing on deck and snorkeling in the gin clear sea.

This glamorous villa is situated on Capri’s main road—and just a five-minute walk to the port—but JK Place feels like a refuge from the tourist throngs. Interiors have a chic, polished aesthetic that’s the embodiment of la dolce vita: The crisp white-and-navy spaces are filled with beautiful art and antiques, dramatic fireplaces, and colorful bouquets of blooms, while large windows and panoramic terraces capture views of rugged green hills that fall into the sea. (Yes, that’s Mount Vesuvius looming in the distance.) Posh touches continue in the guest rooms—think monogrammed pillows, canopy beds, wingback chairs, and marble- and mosaic-tiled bathrooms. Lemon trees scent the air throughout the property, from the elegant pool deck and on-site spa to the terrace bar, where sunset aperitivos are accompanied by tasty bites such as sea bream sliders and quail-egg canapés.

Few visitors venture to Duncans Bay, a small town in northern Jamaica, halfway between Montego Bay and Ocho Rios. But its public beach, called Fisherman’s, is one of the best for a local vibe. The scenery is straight out of an old Caribbean postcard: kids play in the distance, colorful fishermen canoes rest on shore, and a ramshackle bar along the wide golden sands attracts the usual neighbors. Show up mid-afternoon, when the grill and some background music get started, while the waves splash and the sun prepares to set. The slow rhythm of this area, away from the resorts, vendors, and tourist trails, will make you want to stay for hours. No problem—there are local guesthouses a stone’s throw away.

Starting at the sea gate, pick up a map from the tourism board office to get oriented. Then, wander past innumerable shops and cafés, taking note of Korčula’s fishbone layout, which was intended both to protect the town and make use of local winds. Also be sure to admire Korčula’s signature stonework, best displayed in the Gothic-Renaissance-style St. Mark’s Cathedral.

Located in South Walton—roughly in between Panama City and Destin on Florida’s scenic coastal route, 30A—Rosemary Beach’s perfect white sand and clear turquoise waters are as close to the Caribbean as Florida comes. Unless there’s a storm a brewing, the Gulf of Mexico waters are delightfully calm and very nearly lake-like, making the beach a favorite for families with young children as well as those who love paddleboarding and kayaking (you can rent gear nearby). And classic Gulf of Mexico sunsets, as you might imagine, are another Rosemary Beach specialty.

Need a break from the hot weather at the beach? Want to unwind and relax in the lap of luxury? Look no further than the beautiful cliff-side Royal Isabela resort. The fresh rum punch is delightful here. It’s one of my favorites on the island (each place has a distinct version). I didn’t ask for the recipe but I’d rather keep it a secret—to keep me coming back to this beautiful place. The resort has a breathtaking view, with private villas and a golf course. I come here to take in the beauty of the Caribbean away from all the crowds and parties. It’s serene and lush.

Set back in a leafy area behind Casino Square and facing the sea, the sprawling, elegant Hotel Hermitage is a slightly less ornate alternative to the glittery fussiness of Hôtel de Paris, though it’s equally steeped in neoclassic grandeur. Many of the rooms and suites feel more contemporary than the hotel’s hand-painted Belle Epoque frescoes and stained-glass winter garden lobby dome designed by Gustave Eiffel. Accommodations range from rooms with clean lines, soft colors, and walnut furnishings to the most sought-after suites, with private terraces and lovely sea views. Because of the hotel’s spaciousness, it’s particularly well suited to families who want a touch of nostalgic glamour along with high-tech plasma screens and other modern amenities. The hotel’s V.I.K. (very important kid) program offers everything from a game room with activities to access to the private beach and pool for children.

A delightful peach-colored villa set directly on Treasure Beach, this Jamaican-owned guesthouse is a gem, and feels more like a vacation home than a hotel. There are six spacious guest rooms and two larger suites, each with their own patios or balcony with a glorious sea view. The interior is intricately decorated with carefully chosen African-themed paintings and sculptures, and the owner—who returned after many years in the US—takes pride in providing true Jamaican hospitality. There’s a bar and no restaurant on site, but that doesn’t prevent the large kitchen and staff cook from taking your daily orders for breakfast and dinner, dishing out excellent local specialties that are served poolside with the sea in front of you. It’s one of my favorite places to stay and get away from it all.

A spectacular demonstration of a natural sculpture, these sedimentary limestone layers were once layered horizontal at the bottom of the sea. They’ve been folded and crushed with huge tectonic forces for thousands of years and now their sharp edges point vertically up to the sky.

You can’t go wrong with any of the Intercontinental David’s rooms, all 555 of which look out onto the Mediterranean, but those seeking the ultimate view should at least consider the Jaffa Suite for its privileged perspective on Old Jaffa, or the Tel Aviv Suite, where the panorama includes Jaffa, Tel Aviv, and the sea. On the other hand, this hotel is so centrally located that you could simply walk to anything you want to see, from the evocative old city of Jaffa with its minarets, stone walls, and bobbing boats, to the Neve Tzedek district full of bohemian cafes and boutiques. Although you’ll be tempted to fill up on produce, halva, and pastries at the nearby Shuk HaCarmel market, save room for at least one dinner at the Intercontinental David—especially the traditional Shabbat meal that takes place in the third-floor Jaffa Court on Friday nights.

Shangri-La’s Boracay Resort & Spa is located in one of the Philippines’ most popular vacation spots. And while it has all the musts—the turquoise waters, the powdered-sugar shores, the lush hills—what it doesn’t have is the crowds. And therein lies the resort’s beauty, or at least some of it. Tucked into an eco-reserve with its own shimmering beach, the Shangri-La is also home to a canopy-cloaked dining aerie, sunset-surveying clifftop cabanas, and a peninsular spa on a private bay. Accommodations are impeccably appointed with local touches (think woven abaca rugs and lamps bedecked with capiz shells), and several of the lodgings feel more like private vacation homes. Take the aptly named treehouse villa, for example, where the canopy-level second story commands stunning sea views (best enjoyed from the hot tub on the balcony), or the pool villas, where the lure of en suite swimming almost overpowers the sea just outside.

Travel on the large island of Luzon, in the Philippines, can be rough, to say the least, due to traffic-congested roads and road blocks, but if you can make your way to the farthest point north on the Philippine Archipelago you will be rewarded by a true paradise called Pagudpud Beach! The sand is white like sugar and the water crystal clear. The bay is filled with a plethora of wildlife and sea creatures, and the calm waters are perfect for snorkeling right from the sandy beach. Although Pagudpud is a well-known tourist destination, I have never seen the beaches packed with tourists (my family is from a nearby village called Bacarra) and it isn’t hard to find a long stretch of beach to have all to yourself. The beaches here are truly remote. Spend the entire day snorkeling and eating fresh fruit and seafood that can easily be purchased roadside. I recommend staying for the sunsets, which are magnificent over the China Sea.