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For more than half a century, this two-story, largely South Indian vegetarian joint on busy Serangoon Road has pleased palates with its tasty array of dosas—black-lentil-and-rice crepes designed to be ripped into pieces and dipped into heavenly chutneys and sauces. The restaurant’s prices and decor are humble, but the flavors are rich. Choose a tubular or cone-shaped dosa, or ask for one stuffed with potato, onion, or chilies. Other smart orders include buttery naan with a bowl of vegetable curry and Indian-style spinach with cubes of paneer (cheese). The biryani saffron-rice dish is also popular and is served with vegetable curry, dal, raita (a cooling yogurt concoction), and other accompaniments.

Located in the charming harbor town of Portpatrick, Campbell’s is the perfect combination of welcoming informality and smart professionalism—with views of pleasure crafts and fishing boats, to boot. The best dishes highlight the fruits of the sea, whether it’s grilled langoustines or poached halibut, but also worth trying are the Thai green curry, the surf-and-turf with Galloway beef, and desserts like chocolate marquise and crème brûlée. Most ingredients come from the nearby coastline and surrounding farms, and bread is made daily on the premises. There’s also a decent wine list for pairing with your meal. Designed to mimic the seaside, the dining room is done up in shades of green, blue, and gold, with fresh flowers, candles, elegant glassware, and rustic cutlery lending the restaurant a homey yet elegant feel.

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.

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.

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.

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.

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.

Drive along the main road from Sea Cows Bay to Road Town and you’ll come across numerous roadside tents selling everything from fresh fish to local fruits. The best stands are located close to Carrot Bay, where you can find steaming pockets of fish cooked in foil and fresh-squeezed mango or guava juice.

Want to look like the hippest, sharpest, coolest dude in town? Whether you’re going for pretty-boy appeal or a sexy lumberjack look, this South Congress spot has you covered. In addition to high-end denim, retro bathing suits, Pacific Northwest–inspired sweaters, and slim-fit suits for a night on the town, STAG sells the other stuff that a worldly man needs: from cologne to leather goods to personal-care products. (After shopping, reward yourself with a pie from popular Home Slice Pizza next door.)

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.

Plan on spending the better part of a day at the National World War II Museum, even if you profess limited interest in history. This fine, sprawling museum—formerly the D-Day Museum—is affiliated with the Smithsonian Institution, and was established here because of the role the locally made Higgins landing craft played on D-day. Don’t expect the usual repository of static artifacts, like machine guns and airplanes—although you will find those on display. It’s more about gathering stories, from film and oral histories, and from all sides of the conflict. The museum was the idea of Stephen Ambrose, noted author of books about WWII, who wanted to share with the public the interviews that didn’t make it into his books. It’s grown massively since its humble beginnings, and does a remarkable job of capturing the era through both a microscope and wide-angle lens.