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Built in 1857, this historic, wood-beamed pavilion enjoys a park-like setting right on the beach. Folding French doors create the feel of open-air dining, and the simple but satisfying menu (salmon, filet mignon, duck breast, and burgers) gives you the impression that you’re dining at your own private club. One of the west shore’s most photographed locations, the outdoor bar at Chambers is also one of the area’s biggest party spots on summer weekends. Arrive by boat or car, but if you’re the designated driver, steer clear of the infamous Chambers Punch, a lethal concoction of rum, orange juice, and pineapple juice. Note: The restaurant is open May to September only.

Feast on fresh-caught fish and seafood and wash it down with Italian wine during a leisurely summer lunch at Alla Maddalena on Mazzorbo Island. A 45-minute ferry ride from Venice and far removed from the crowds, this charming, less touristy and altogether tiny island in the Venice lagoon is wonderful place to escape for an afternoon. And Alla Maddalena serves amazing fried fish as well as top-notch mussels and clams, all of which can be eaten al fresco either in the back garden or by the canal. The trattoria is also known for handmade pastas and seasonal ingredients from fruits to locally hunted game like wild duck. (Mazzorbo is a short walk across footbridge from Burano Island, so if you’re planning a trip to Burano, you can add a stop here for dinner.)

The city’s iconic wood-paneled Tram 28 rambles along a 4.3-mile route from Campo de Ourique to Praça Martim Moniz, navigating tight turns and steep inclines as it passes some of Lisbon’s most endearing attractions. Originally commissioned in the 1930s, these classic Remodelado trams were in fact enlisted for their ability to handle Lisbon’s hilly terrain. They can get painfully crowded—wait times can be outrageous in the high season—so catch an early ride (5:40 a.m. most weekdays, or 6:45 a.m. on Sundays) for unobstructed views of hilltop neighborhoods like Graça and the Alfama.

No matter what kind of getaway you have in mind, you can find a guestroom to fit at Castle Hill Inn. Rooms in the main house vary in size and décor, but each is kitted out for romance with a fireplace, a king-sized bed, oversized tubs, and windows looking over the water and expanses of lawn. The Turret Suite, a bi-level space, has a bedroom on the first level; on the top floor, a soaking tub on a raised floor takes advantage of the 320° wrap-around windows. Below the main house, the Harbor House’s modern guestrooms feature front-porch views of Newport Bridge and the hotel’s Grace Kelly Beach. At the far end of the 40-acre property, the Beach Cottages and Beach Houses are set along the private beach, offering views that take in both the mansions along Ocean Drive and the wild Atlantic itself. The cottages, slightly smaller and closer to the beach, have peaked ceilings with rafters. The airy Beach Houses, compactly outfitted with galley kitchens, sunny decks, ceiling fans, fireplaces, and curated shelves of books, cast a kind of never-leave spell.

Every day at noon at the Plaza de Armas (also called Plaza Mayor), trumpets blare, drums pound, and cymbals crash as the guard changes outside the presidential palace. Enjoy the Spanish fanfare like a local: from a plaza bench with an ice cream cone. The Plaza is also the site of festivals, concerts, and the much-loved annual National Pisco Day when the fountain spouts free high-proof grape brandy for all.

The Western Wall (also called the Kotel) is a remnant of the ancient wall that surrounded the Jewish Temple’s courtyard in the Old City of Jerusalem. It is one of the most sacred sites in Judaism, outside the Temple Mount itself. The plaza in front of the wall is divided into separate sections for women and men. Some worshipers wedge their prayers, written on small scraps of paper, into crevices between the stones in the wall, while others stand and pray, sometimes for hours. Archeologists have uncovered layers of the wall underground through years of excavation, and via a guided tour, visitors can walk through areas of this original, unrestored site that dates back to the 1st century C.E.

The historic and modern center of the city, the Piazza del Duomo (the square surrounding the cathedral’s base) remains a popular meeting place, hangout and hub of Milanese life. Local vendors setup shop (selling fresh coconut in the summer, toys and tourist wares), kids run and play (free from traffic) and shoppers trickle in from the walking street surrounding the huge plaza. The statue of Victor Emmanuel II, the first king of Italy, is the best place to meet, sit, recharge and watch the city go by.

Peruse the wooden shelves stacked with coffee table books about art and architecture, take in the sandy beiges of the wicker chairs and the sky-blue pillows and tiled walls, and you may think you’ve fallen into a coastal California dreamscape. The menu at this restaurant inside the über-chic South Congress Hotel also evokes California, with grain bowls, salads topped with lean protein, and fashionable avocado toast. The kitchen, which serves breakfast, lunch, and dinner, doesn’t appeal only to the calorie- or trend-conscious, as evidenced by a great throwback cheeseburger draped with American cheese. Executive pastry chef Amanda Rockman is also one of the main attractions here, with her stunning creations, such as an airy kouign-amann.

Malacca was under Dutch rule from 1641 to 1795 and then again from 1818 to 1825, and the buildings along Dutch Square reflect this history, all painted in terra cotta—the square is also often called Red Square, because of the color of the buildings that sit on it. Just behind the square’s clock tower, the Stadthuys was built in 1650 as Malacca’s city hall; it continued to serve this purpose even after the British took control of Malacca. It’s believed to be the oldest Dutch building in Southeast Asia. The large but simple building has white wooden shutters and a tiled roof. Today, the Stadthuys houses several museums, including the History and Ethnography Museum.

The Caramoan area, on the eastern tip of the Caramoan Peninsula in Bicol, is a rugged and remote landscape of white-sand beaches, rich woods, swampland, lakes, and caves. Numerous seasons of the reality TV show Survivor have filmed around this region, including at Gota Beach. Most travelers explore the pristine Caramoan Islands by small outrigger boat. There are too many to scope out in one trip, but don’t miss famous Matukad Island with its pure white sands, exotic rain forest, limestone rock formations, and even a hidden lagoon. Another must-visit is Manlawe Island, a one-kilometer-wide sandbar surrounded by ankle-deep water. Other highlights include Cotivas Island, Gota Island, and Sabitang-Laya, a triangular landmass with powdery sand, caves, and superb snorkeling. Accommodations in Caramoan include family-run inns that are equipped with modern amenities but rustic enough to accentuate the region’s remote and unspoiled ambience.

Put on your comfortable shoes and head to the many trails of Cayman Brac to see wildlife, as well as scenic and geological sights. There is a path for all skill sets. Listen to the mating calls of the parrots flying above at the National Trust Parrot Reserve Hiking Loop, or descend carefully into Peter’s Cave and move through the various layers to discover a truly breathtaking natural wonder. Most hotels have a brochure of all the hiking trails; this includes images, difficulty, and a brief description of each trail.

Eating raw herring is a right of passage for many who visit Amsterdam. Order yours from the friendly Dutch matrons in blue and white-striped aprons at Stubbe’s Haaring, a herring stand with a view on the bridge over Singel Canal, just off Haarlemerstraat. For decades, this local institution has satisfied the fish cravings of Dutchies and visitors with lightly brined herring, smoked eel and other delicacies from the North Sea. Unless you want bragging rights, there’s no need to eat your buttery snack Dutch style, grabbing it by the tail, throwing your head back and lowering the fish whole into your gaping mouth. Most locals eat it in a less flashy way: cut up into small pieces, covered with onions and sweet pickles, topped with a Dutch flag. It’s served on a waxed paper plate, sans bread or cutlery. Use the flag-festooned toothpick to stab the soft, mild-flavored morsels and bring them to your mouth. For a more filling meal, order a broodje haring (herring sandwich) on a soft, white bun, filled with fish, pickles and onions. Eet smakelijk!

Wonderful catamarans that you can rent right off the beach.

The Metropolitan Museum of Art—or, commonly, the Met—is one of the world’s great museums, alongside the Louvre, the British Museum, and a handful of others. It would be easy to devote an entire week’s visit to the museum alone, and realistically you probably won’t get far beyond a few exhibitions and galleries at one shot. The Costume Institute’s temporary shows are always popular, while others will (like the museum itself) focus on a range of regions and periods—at any one time there may be temporary exhibitions on an Italian Renaissance painter, miniatures from Mughal India, and Polynesian carvings. The Temple of Dendur, a roughly 43' x 21' x 16' temple that dates to around 15 B.C.E. and was given by the government of Egypt to the United States in 1967, is one of the museum’s most photographed (and Instagrammed) works. The 34 period rooms, including a 12th-century cloister, English parlor and a Shaker “retiring” room, are among the museum’s other highlights. On summer evenings, site-specific installations make the rooftop terrace is a favorite place for drinks. The general admission of $25 for adults, $12 for students, and $17 for seniors is a suggested one for New York residents, as well as students from New York, New Jersey, and Connecticut. Whatever you pay also includes same-day entry to The Met Cloisters.

A short walk from the city center, Koombana Bay is famously frequented by cavorting bottlenose dolphins; in its calm waters, you may even find yourself swimming right next to one of these remarkable creatures. The wide, white-sand beach is easily strollable, with views of boats from the nearby Koombana Bay Sailing Club. Beach volleyball is a big sport here, and the restaurants and cafés of the nearby Marlston Waterfront are popular with both locals and visitors.