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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.

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.

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.

Out of the tragedy of the plague arose the Karlskirche, perhaps the most magnificent of Vienna’s baroque churches. One of the final designs by Johann Bernhard Fischer von Erlach, the genius behind the Schönbrunn Palace, Karlskirche commemorates the outbreak of 1713. The Karl who gave the church its name was the Counter-Reformation’s Saint Charles Borromeo, who cared for plague victims in 16th-century Milan. The church dome, rising above two columns inspired by Trajan’s Column, is illuminated at night and is a prominent Vienna landmark which be seen from many points in the city. A vibrant fresco in the cupola by Johann Michael Rottmayr glorifies Saint Charles. On Karlsplatz, in front of the church, two of the legendary architect Otto Wagner’s finest art nouveau metro stations remain; one of them now houses a café.

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.

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.

Key West’s most famous literary resident, Ernest Hemingway, lived in this two-story Spanish-colonial villa for nearly a decade and composed several of his best-known works here. His second wife, Pauline, insisted they add a pool to the spacious grounds—the first inground pool in Key West. The cost ballooned to around $20,000, a fortune in the 1930s, and was said to have contributed to the breakup of their marriage. It’s just one of the fascinating stories guides will share on the half-hour tour of the home and gardens (included in the price of admission). And yes, you’re guaranteed to see plenty of six-toed cats, descendants of Hemingway’s original six-toed cat, Snow White.

Auntie or Teta Smilja, as locals lovingly call her, opened her cozy shop back in 1994. Since then, her sweets—made using traditional and original recipes—have been featured in international magazines and won national awards. Packed to go, her klaštuni (walnut-filled dough) and amareti (almond cookies with lemon and orange) will make your walk around Korčula memorably sweet.

The former residence of Würzburg’s prince-bishops, this UNESCO World Heritage site is one of the most important Baroque palaces in Europe. It was—remarkably, given its scale and level of detail both inside and out—built almost entirely within a single generation. Court architect Balthasar Neumann oversaw the construction, while leading architects from Germany and France created the fabulous ornamentation. Woodcarvers, sculptors, and artists from Italy—including Giovanni Battista Tiepolo, regarded as one of the greatest fresco painters of the 18th century—also contributed to the design.

Rebuilt after World War II, the palace now features a bevy of architectural styles, from German and Viennese Baroque to French château. Inside, the White, Imperial, and Garden halls are can’t-miss attractions, as are the grand staircase and ceiling fresco by Tiepolo and the Mirror Cabinet. Before leaving, be sure to take a walk in the court gardens, which feature fountains, charming yew trees, and a group of cherub statues by Johann Peter Wagner.

Among the neighborhood’s art-minded hotels, the Gladstone is the most interactive, with shows, classes, and ongoing events. The 37 rooms, all designed by local artists, have breathed new life into the 128-year-old icon, which filmmaker Christina Zeidler took over in 2003 and revitalized in 2005. The Victorian landmark, named for its avenue (in turn named after four-time Canadian Prime Minister William Gladstone), has been a gathering spot for over a century. And it was home to legendary Toronto characters like cowboy Hank Young, who became a fixture at the hotel as a country singer in 1961 and manned the hand-operated elevator from 2005 to 2009, and Peter Styles, former host of Karaoke Night, with applause sign in hand. The legend of Hank lives on in a framed photo in the stairwell en route to the second floor.

The Gladstone continues to push the boundaries of community and culture with creative events like its educational workshop series, Get School’d, and its annual alternative design event, Come Up to My Room (CUTMR), which runs alongside the city’s Interior Design Show. Begin your stay in this architectural gem with a drink at the Café or Melody Bar (that is, if you’re not first thrust into Fameless Karaoke Night).

Nature may have spent 12 million years creating the rock formation that is the centerpiece of this 1,300-acre Hilton Curio Collection resort in the foothills of the Sonoran Desert, but late-coming humans have done a commendable job of adding the finishing touches. Although the Boulders, with its casita accommodations blending into the landscape, its championship golf courses, and its upscale shops, is as luxurious as any resort in the Scottsdale area, it’s also where guests are most likely to feel they are truly in the desert. An early-morning walk along groomed paths, when the first rays of light are turning the landscape golden, is as likely to produce the sounds of woodpeckers or owls calling from their nests in saguaro cacti as it is the whack of a ball against club or racket.

Owned by the world-renowned art collector Dakis Joannou and smartly decorated by quirky Brazilian designers the Campana brothers, the New Hotel is the city’s coolest upscale design-centric property, with 79 rooms (including seven suites) and an intimate restaurant. Although centrally located, just a five-minute walk to Syntagma Square, it’s tucked back in a modernist building on a side street so it feels hidden and discreet. The interiors are both playful and smart; the Campanas created much of it with items recycled from the previous hotel. Imagine puzzlelike walls and chairs constructed of layered, repurposed wood intermingled with sculptural chairs of their own design. In the rooms, they had fun riffing on Greek cultural objects, like the Karagiozis, a shadow puppet, and multiple versions of the glass “evil eyes” used to protect against ill omen. Bottom line: stylish contemporary design, excellent location, and friendly service.