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Perched high above the Bay of Positano, Il San Pietro is the epitome of Italian seaside glamour—the hotel has attracted a coterie of international VIPs since its opening in 1970, including Gregory Peck, George Clooney, and Julia Roberts—but retains the charm of a family-run inn. Michelin-starred Zass restaurant culls ingredients from the property’s organic gardens, which spill down to the sea across 10 terraces teeming with local produce, and rooms feature custom ceramic tiles made in local factories using traditional techniques. If the 400 steps down to Positano’s only private beach sound daunting, an elevator cuts through the rock to water level, where tangerine loungers on the stone sundeck give way to a cove with sandy shores. Here, breezy Carlino restaurant serves up lemon spaghetti beneath a cheerful thatched roof. Prefer more active endeavors? Hugging the cliff face above, seaside tennis courts serve up sets with a dazzling view.

Gothic and grand, this 18th-century former nobleman’s home stands proudly on the banks of the Grand Canal in the San Marco district. Venetian-born owner and interior designer (among her many talents) Francesca Possati has restored this historic home to its regal glory. She has worked with local artists to breathe new life into original woodwork, ornate trompe l’oeil ceilings, and silk wall hangings, resulting in a once-again polished and posh palazzo. The distinctly Venetian rooms—many with canal views—are styled with rich fabrics, bold wall coverings, and pristine period antiques and illuminated by Murano glass chandeliers. Of course, they’ve been updated with the latest modern perks (like Italian marble and whirlpool tubs in the bathroom).

Stroll the art-filled hallways, splurge for a tasting menu at the elegant restaurant, and watch the gondolas float by from the red-awninged terrace. La dolce vita, indeed.

Chef Cristian Angiolin heads up the kitchen at this Venetian lagoon institution, which is open year-round except for January and Tuesdays. The restaurant is no longer a part of the Cipriani franchise, which began in Venice and has since expanded to places like New York and Miami.

What you come here for is the restaurant’s garden, which is open from late spring to early autumn and is one of the best places in the lagoon to visit with a large group of friends and celebrate into the evening. The bartenders make the best negronis and have an extensive wine list that includes pours from most regions on the Italian peninsula. If you don’t want to be marooned on Torcello Island, come for lunch. But it’s another one of those amazing dining spots with rooms, so that if you do come for dinner and miss the last boat back to Venice, you can always check into the hotel.

Family style restaurant where you can sample virtually everything on the menu. Salad sampler, pasta sampler, meat sampler. GET IT ALL

The Piazza Della Repubblica was the place to be in Florence in the evenings. Tourists and locals alike dined at the restaurants lining the square, student groups gathered, families enjoyed the Carousel, and gypsies and other migrants tried to sell everything from silk scarves to toys..right up until the police arrived and they all magically disappeared.

The Milan Cathedral, or Duomo, occupies a site that’s been holy since the time of the Romans, but it wasn’t until the early 19th century when the finishing touches were finally placed on this massive building. The Duomo is the fifth largest cathedral in the world and one of the top tourist sites in the northern Italian city. Entrance is free, but a small fee is requested if you wish to take photos. Inside the church is even more magnificent then the outside, with scores of shrines and altars dedicated to saints and notable Milanese. During the Christmas holidays the city’s night market takes up residence next to the cathedral, adding one more reason to visit this central site.

This Ferragamo-owned restaurant is located on the river with in-your-face views of the Ponte Vecchio for the lucky few who manage to book one of the tables on the terrace. Chef Peter Brunel has been making waves with his creative menus: Borgo San Jacopo has been awarded a Michelin star for the past several years in a row. Yes, it’s expensive, but with a tasting menu featuring dishes such as porcini mushroom ice cream and fig molasses and risotto with sea urchin, it’s a meal you won’t soon forget.

A fully vegetarian menu is also available, as is a wine pairing for those adventurous eaters who would prefer for the team’s experienced somms to take the lead.

The second property in the Bulgari Hotels collection is an Italianate stunner perched on the cliffs of Uluwatu, a region at the southern tip of the Bukit peninsula. While the hotel’s vibe stays true to the brand’s roots, hand-hewn volcanic rock, Javanese mahogany, and exclusive fabrics banded and bordered by local artisans reflect the heritage of the archipelago. In fact, Asian-European duality is a prominent theme here: One restaurant focuses on Indonesian fare, while the other is a formal reflection of Italian culture. Watching over the resort at its highest point sits a temple, which employees use to perform daily rituals, as well as a traditional guardian—the Hindu elephant Ganesh. And at Bulgari’s base is a private stretch of sand accessible via an inclined elevator.

Tucked in an alley near the historic downtown you’ll find this small restaurant serving traditional, regional dishes (at a great price especially for the area). With open-air courtyard seating surrounded by vines, it makes for a relaxing lunch. For the best and freshest thing on the menu, take advantage of the friendly staff and ask for a recommendation– they’ll point you in the right direction. If you’re like me and spend the entire day walking until you’re ravenous, this is a great place close to the Duomo. Try the stuffed zucchini flowers (one of my favorites in any Italian restaurant)!

The Hotel Locarno occupies two adjacent buildings in the cosmopolitan district between the Tiber River and Piazza del Popolo. The original property, built and inaugurated in the 1920s, houses the majority of the standard and deluxe rooms, while the annex, a former palazzo owned by a Venetian family, houses the more luxurious suites. Both of the adjoined structures blend Old World charm and art nouveau elegance, and their rooms preserve turn-of-the-20^th-century decor, including lavish drapery, oil paintings, embellished ceiling stuccoes, and period furniture.

The two buildings are joined by a wisteria-filled courtyard, where breakfast is served in fine weather. The rooftop bar offers aperitivo (the Italian version of happy hour) cocktail service and sweeping views over the city and across the river to St. Peter’s cupola. The bar is open to the public and attracts a well-heeled Roman and expat crowd.

The Belmond Villa San Michele knows something about history. Michelangelo designed its facade, Franciscan monks tended its gardens, and Brigitte Bardot stayed here. But, like any elegant host, it’s not brash about its pedigree. Manicured Italian gardens—designed by 15th-century friars—beckon you for sun-soaked strolls. The colonnaded loggia is a pleasant place for a sunset aperitivo or candlelit dinner, especially with a view of Florence and the Arno Valley. The hotel’s expansive rooms are already decked out in the most tasteful, almost understated interpretation of Renaissance luxury—terra-cotta tile floors, heavy wood furnishings, just a dash of red velvet, and plenty of cream-colored walls—and then the panoramic views, original frescoes, and modern Carrara marble bathrooms steal the show. There’s a real-deal cooking school, where the chef actually works with each person in hands-on preparations—no demonstrations-only here. Other perks include the hillside pool, the concierge service that can get you into the Uffizi outside of operating hours, and, from the Loggia Restaurant, a view of the ancient Roman road that once connected Florence to Fiesole.

The Rome Cavalieri, like the Hassler and St. Regis, is synonymous with five-star luxury in Rome. The hotel, opened in the 1960s, channels a Versailles-meets–Dolce Vita vibe, and given its unbridled opulence, it’s a top destination for honeymooners and jet-setters seeking the ultimate comforts. Its location atop Montemario, a hillside residential district north of the Vatican, offers spectacular views of the city from various terraced levels and many of the rooms. The very location, affording such panoramas, is also a drawback for travelers wishing to be in the thick of it all, so the Rome Cavalieri is best suited to those who relish spending significant time in the hotel rather than out on the town.

There are plenty of appealing amenities for guests who choose to stick around the property. The outdoor pools, the finest in Rome, are set amid lush gardens. The pool area doubles as a sort of private club for local elite and is ripe for Italian athlete and celebrity sightings. Back inside, the lobby and rooms are sumptuously furnished and feature antiques and original works of art.

A key component to the mastery of a skill is knowing when to break the rules. As its name implies, Jovanina’s Broken Italian breaks away from the traditional rules and expectations of Italian cuisine with the measured confidence of a master. Owners Jennifer and Jake Linzinmeir bring years of restaurant experience, both in the kitchen and in management, to Jovanina’s, which allows them to find an approachable balance of new flavors and classic dishes to the menu. The airy ground-floor space feels festive, with whitewashed brick walls along one side and a bar running the length of the other; a downstairs wine-bar dining area has a quieter, more intimate vibe. Try any of the handmade pasta specials or go with the favorite: a brick-oven pizza topped with fennel sausage, smoked mozzarella, and caramelized onions.

If you’re a shopper, then Bologna is the city for you. Thanks to the combination of a large student population and a robust corporate climate, the ability to spend some money shopping abounds. One of the top buys can be found at the many food shops around town. Bologna is one of the culinary centers of Italy and you can find everything from the freshest of foods to the coolest of kitchen gadgets around town. This is also northern Italy, so fashion is always close at hand as well. If high-end labels are your thing, then a walk through the main shopping district won’t leave you disappointed.

La Piazza is regarded as one of the finest Italian eateries in New Delhi. And rightly so. It’s been highly ranked by various local magazines year after year. Every bite of every dish oozes with freshness and is cooked to perfection. It’s one of the few restaurants where I found that they offered healthy substitutes such as whole wheat pasta. The ambiance is dimly-lit and romantic, mimicking somewhat of a sidewalk Italian cafe with cascading white pillars, stone tiles, and wooden louvres. Top off your experience with scrumptious desserts and crisp Italian wine…and VOILA, you’re in Italian heaven! As expected, the dress code is upscale and classy. They will refuse service, so dress up! To try: the wood-fired pizzas!