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This spot near Eagle Beach is pure Caribbean. The live music is infectious, the plates come piled high, and the tables are situated outdoors, under the sky or a tin-roof overhang. Plus, there are more local patrons than visitors. While the atmosphere is laid-back, the menu is full of sophisticated presentations, from island favorites to international dishes. Popular picks include the crab cakes, almond-dusted grouper, and lobster ravioli. The wine list is also excellent, as is the craft beer selection. Note: Reservations are recommended. The restaurant is closed on Sundays.

The second, and smaller, inhabited island of Îles des Saintes is Terre-de-Bas, reached by boat shuttles from Terre-de-Haut. There’s not much to do here other than explore nature in its wildest state, but one of the sights that makes it worthwhile is the only beach on the island: Grande Anse. It’s mostly undeveloped and rarely crowded, and offers nearly a mile of golden sand and blue bay water. You’ll find a local restaurant there for a plate of fresh seafood and rice, at cheaper prices than on Terre-de-Haut.

With sand between your toes and frothy waves running over your tired feet, enjoying a long walk on the beach with your beau is about as romantic as life can get. Many hotels make it easy on couples, thanks to their convenient waterfront location, but Hapuna Beach on the Big Island and Honokahua Bay on Maui are two other pacific coves that inspire hand-holding and quiet whispers. For complete intimacy, Lumahai Beach—fitted into the bay near Hanalei on Kauai—is difficult to find, but its remote coast and soft sand have been the scene of more than one knee bent into the sand for a proposal.

Said to be the oldest structure on the island, Wallblake House is also the only surviving 18th-century plantation home that has been restored and that can be toured. Located in the Valley, capital of Anguilla, the 1787 property was once part of a 97-acre sugar and cotton plantation. Bestowed to the Catholic Church in 1976, it was abandoned until it was finally refurbished in 2004. The main home, which suffered a fire at the hands of the invading French forces, and the outbuildings are intact in design. Though the house is currently used as a rectory, tours can be arranged by emailing in advance.

Anguilla is blessed with numerous talented artists, but Cheddie Richardson has long been a standout on the island for his carvings. A craftsman since his childhood days and with no formal training, he grew famous over the years—both locally and internationally—for his unique pieces depicting various types of Anguillan flora and fauna, including birds, fish, and turtles. His studio is filled with them, fashioned from driftwood, mahogany, walnut, coral, or stone; there are a few bronze pieces as well. In 1994, one of Cheddie’s carvings was given to Queen Elizabeth II during her official visit to Anguilla, and it now sits in the Royal Collection.

Finding a table with a view, friendly service, and menu prices that don’t make you gasp is a rare thing in Capri. Ristorante Villa Margherita offers all three. Sit under the pergola at lunchtime, and take in the blues and greens of Marina Piccola down below. After dark, the space twinkles with soft lights and candles. Island classics such as insalata caprese and spaghetti alla Nerano, made with zucchini and provolone, are featured on the menu. Finish on a cool refreshing note with paper-thin slices of pineapple carpaccio marinated in ginger.

Active from the 13th to 15th centuries and considered an influence on the pre-Renaissance movement, the Sienese School of painting is identifiable by its themes—always religious, and usually with a focus on Biblical miracles—and its signature style, a dreamy mix of Roman, Gothic, and Byzantine influences that often feature dazzling gold backgrounds. Opened in 1932, this museum boasts one of the world’s largest collections of Sienese School works, as well as a number of Renaissance and late-medieval pieces from Italian artists. Wander through the impressive building—a combination of two 14th- and 15th-century noblemen’s palazzi—to find works like Duccio’s Madonna and Child, Michelino da Besozzo’s Mystical Marriage of Saint Catherine (celebrating the “calling” of Siena’s native daughter), and Bartolo di Fredi’s expansive Adoration of the Magi. Paired with a visit to Florence’s Uffizi, coming here offers insight into the differences—and longtime rivalry—between the two cities.

In 1911, American star jockey Tod Sloan took a bar in Manhattan, dismantled it, and shipped it to Paris. At the time, American tourists and members of the artistic and literary communities were beginning to visit the City of Light in ever-increasing numbers, and Sloan wanted to capitalize on his fame and make the place a spot where expats would feel at home. Over the years, Harry’s New York Bar has been frequented by a number of famous Americans and international celebrities, including Sinclair Lewis, Ernest Hemingway, Coco Chanel, Jack Dempsey, Rita Hayworth, Humphrey Bogart and the Duke of Windsor. Whether or not you have star status, you can still settle in on a stool with a drink and soak in the history.

If you’ve developed a taste for the flavors of the Caribbean during your cruise, stop at this small spice shop to take some home with you. It’s hard to miss, since it’s located upstairs from the ferry dock. The owners hand-mix most of their signature spice blends. The top seller, Cruz Bay Grill Rub, is a potent dry rub that combines nutmeg, cinnamon, fennel and other spices. The shop also sells island-made candles, rum balls and hot sauces—but watch out for the one made with searing Scotch bonnet chili peppers, a favorite in the Caribbean.

In the shadow of Buckingham Palace lies Fortnum & Mason, the department store with a royal warrant famed for its loose-leaf tea, luxury picnic hampers and sweet treats, including an excellent selection of macarons. You can buy all of these inside the store, as well as browse the gentlemen’s department, and cast your eyes up to the spectacular atrium, but the real highlight of a trip here is the afternoon tea, served in a gilded Diamond Jubileee Tea Salon, opened in 2012 for the Queen’s Diamond Jubilee. An accompanying piano player sets the tone: at high tea, you can expect a charming display of finger sandwiches, individual pastries and cakes from the cake carriage, and scones served with Somerset clotted cream and Fortnum’s lemon curd. The extensive champagne list is also not to be ignored.

House in a restored colonial building, Spencer Cameron Gallery, which is helmed by expat painter Rosey Cameron Smith, sells a mix of art work (sculpture, paintings, blown glass), plus reproductions of island charts and maps. For a unique souvenir, take home some of the gorgeous pottery by local artist Carla Astaphan.

The building is also home to a secluded courtyard café that sells coffee, bread, and cookies, as well as a women’s clothing store called NOMAD. The top floor, which dates back to the 1750s, even hosts yoga classes on Saturday mornings if you’re looking for a good stretch before breakfast.

The colonial town of St. Pierre, on Martinique’s west coast, has a colorful past. Rich from the earnings of the sugar and rum trades, it was once considered the Paris of the Caribbean—until 1902, when it was destroyed by the violent eruption of the island’s largest volcano, Mount Pelée. A volcano museum in St. Pierre displays items plucked from the rubble and historic photos of the town before and immediately after the eruption. Today, the fine church with historic displays bears testament to the town’s comeback.

Sailing is Anguilla’s national sport, but it’s also the best way to explore the island’s dreamy Caribbean shores—and the best way to explore its marine life while in transit. Spend the day with Tradition Sailing Charters, gliding across iridescent blue waters on a 1978 50-foot sloop, drifting from one cay to another. You’re welcome to watch and learn how to sail if you’re a newbie, or to participate if you have experience. After a lunch stop at the only restaurant in Prickly Pear Cays, get underwater to check out this reef-protected bay where sea turtles, blue tang, and numerous other tropical critters thrive. There’s also a brown booby colony on land here.

Just south of the historic center of Québec City, the Battlefields Park is one of the most important historic sites in Canada. Here, the dream of New France—a more than 200-year-long project by the French to colonize North America—was dealt a fatal blow. In 1759, during the Seven Years’ War, British forces under General Wolfe defeated the French troops led by General Montcalm. The battle on the Plains of Abraham lasted roughly 30 minutes. (The very biblical sounding name, by the way, comes from the fact that the land where the two armies clashed was owned by a farmer, Abraham Martin.) After defeating Montcalm (who died in the battle), the British took control of Québec City. By 1760, all of France’s territory in North America had fallen to the British, and in 1763, the French officially ceded their claims. History buffs make a beeline to this national historic site, but Québec residents mostly consider it a lovely urban oasis of 255 acres alongside the St. Lawrence River. In the summer, it’s the setting of outdoor concerts; in the winter, there’s an ice-skating rink (free of charge, and skates are available for rent) from mid-December to mid-March.

After a period of tribal skirmishes, the Fijians suddenly looked up and found they’d been colonized by the British. The Grand Pacific Hotel, built in 1914, shows just what fun it was to be British back then. Built along the same design as a ship—with promenades and prominent views—the Grand Pacific provides an interesting contrast to Waikiki’s old hotels, which all face inland. You can’t tour the Grand Pacific, but it’s worth a walk by or a drink at the bar.