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No Roman holiday would be complete without spending some time, at the very least, window shopping your way through the city. But it will be hard to stave off the urge to buy goods on some of the world’s best shopping streets. (Roads leading to the Spanish Steps tend to be lined with beautiful goods.) Rome’s shops sell exquisite delights from Italian designers, including leather bags, clothes and accessories (the eyeglasses at Ottica Spiezia will make you swoon), and much more. Of course, there are also plenty of food shops so you can bring home the tastes of Rome too.

By one estimate, New York City is home to almost 8,000 restaurants—add in cafés and delis, and the count is closer to 24,000. This list is, needless to say, a mere starting point to the many dining rooms worth sampling, from an intimate Italian restaurant in the West Village to inventive small plates from chef-owner Ignacio Mattos on the Upper East Side.

If you’re after some of the world’s best art, there’s really no better place to be than France. The country is home to a wide variety of world-class museums, from stalwarts like the Louvre, the Musée D’Orsay, and the Centre Pompidou to lesser-known but equally remarkable institutions like the Musée des Beaux-Arts in Tours and the Fondation Maeght in Saint-Paul-de-Vence. Whether you want to see the famously French works of the Impressionists, paintings by Italian and Flemish masters, or more contemporary pieces by the stars of today, you’ll find them all in France.

You can find the best of the best in Milan. Whether you’re in the market for iconic and hand-tailored Italian suits, fashionable bicycles, or a ballet flats, there are artisans and boutiques in this city that will present you with treasures. And design? From haute couture to interior, industrial, and architectural design, some of the world’s most amazing designers, homegrown and international, have set up shop in Milan to showcase ingenious products and style. Come to the market and prepare to be knocked out.

Lauded for its outstanding desserts and for being one of Dallas’ new, hip restaurants, this Italian-food source quickly developed a loyal following of diners. And why not? Between Princi’s robust brunch, lunch, and dinner menus, the ambience at the Preston Road dining spot is at once cool and elegant. Best visit a few times to take it all in!

Nestled within Positano’s hillside tangle of pastel residences and stepped alleys, Le Sirenuse is a legendary boutique hotel that feels more like a private home. Run by the Sersale family since its opening in 1951, the crimson-hued house is filled with antiques, potted plants, and oil paintings that lend it a friendly atmosphere devoid of any snootiness. White-walled guest rooms are accented with Vietri floor tiles and heirloom walnut furniture, while marble bathrooms have whirlpool tubs and Eau d’Italie toiletries, the hotel’s bespoke line. Dining is excellent: The Michelin-starred La Sponda restaurant is as tasty as it is charming, illuminated in the evening entirely by candlelight. There’s also a champagne and oyster bar that commands dazzling views from a panoramic terrace; the vistas are no less stunning from the pool deck, where potted lemon trees scent the air. The hotel also has a top-notch spa, plus fun perks such as free daily excursions on its vintage wooden boat.

Wander along the souklike Via del Saracino until you come upon this large café with a great view over Positano’s main beach. You can have a cappuccino and pastry in the morning, a sandwich for a quick lunch, and then stop in later in the day for a cold treat. (The outstanding popsicles here are made from the juices of Amalfi lemons and other seasonal fruits.) It’s also a great spot to simply sip a beer while taking in the view of the action down on the Spiaggia Grande. For the sports fan, the bar’s multiple screens usually play baseball, soccer, and tennis.

In the center of Trieste, the capital of Italy’s Friuli–Venezia Giulia region, the vast Piazza dell’Unità d’Italia looks out over the deep, blue waters of the Gulf of Trieste. This elegant seafront square is bordered on three sides by ornate Viennese-style government buildings and flanked by the winding streets of ancient Roman “Tergeste” and the grid-like Borgo Teresiano neighborhood. Facing the sea is the Municipio (city hall) building, with its clock tower and two bronze moors. On either side of the square are the stately Lloyd Triestino building and the Palazzo del Governo, whose golden, mosaicked façade sparkles in the sunshine. In front of the Municipio, the angel-topped Fontana dei Quattro Continenti pays tribute to the four continents that were recognized in the 18th century: Europe, Asia, Africa, and America. At the water’s edge sit the intriguing bronze statues of two young women known as Le Sartine, or “the seamstresses.”

Like most Italian cities, Milan has an amazing and very visible history that spans two millennia of art and architecture. But what really distinguishes it from other città is the ever-present testament to modernism and modern architecture—all accessible via the charming vintage trams.

With divine pasta and funny putti, the handsome Duomo and the dreamy young Lotharios leaning on Vespas, with leather workshops and nonnas doing the weekly shopping, Florence offers visitors an urban experience that is equally rich in historic romance and everyday modern life. Join the parade of visitors to worship in the galleries of the Uffizi or watch the parade from a café table beside a busy piazza, but head to this Renaissance stronghold and make your own history.

Italians have a wonderful tradition of winding down the day and gearing up for the night—the early-evening aperitivo. Here are places to enjoy a glass of sparkling prosecco with a plate of savory snacks.

Take two days to explore this coastal town, then venture to other villages along the Italian shores. Be sure to hike from Santa Margherita to Camogli along the edge of the Portofino promontory.

Where to eat the best tapas in Madrid, Sevilla, Barcelona, and San Sebastián—plus how to order them like the locals do.

Passionate Mexico City foodies are rediscovering and reviving Mexico’s rural culinary delights.

A journey through one of the world’s last, best travel secrets.