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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.

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.

Husband and wife team Braden Perkins and Laura Adrian opened this restaurant in the “très Brooklyn” style that’s so popular in Paris now. The food is of American influence, but is made with fabulous French ingredients. We love going here.

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.

Hilton Molino Stucky on Giudecca Island is a zippy five-minute boat ride (free for guests) away from bustling Piazza San Marco, and ideally located for those craving a tad more tranquility without missing out on any of those sweeping Venetian vistas. Once a working flourmill, this brick, industrial-era fortress has been reimagined as a luxury hotel with all of the modern bells and whistles. Take a break from museum hopping with a day spent surveying the city below from the city’s only rooftop pool (followed by quality time spent in the spa). Of course, with several dining options just steps from your room, you could happily spend most of your time right here.

If mixing business with pleasure, this hotel—with Executive Suites, a ballroom for events, several conference rooms, and a business center—makes for a superbly scenic day at the office.

The Hotel Flora is an ivy-clad 17^th-century palazzo tucked down a narrow alleyway in San Marco. It’s hidden from the crowds, but still an easy stroll to the buzz of San Marco Palazzo and the Grand Canal. Like all grand Venetian homes, it’s had its share of interesting inhabitants over the years, including a School of Painting, a salon for well-known local artists. Continuing the artistic legacy, the Romanelli family—photographers, writers, and antique collectors among them—has owned the hotel for the last 50 years.

In the classic manner of a pension, the hotel is intimate and the staff welcoming and friendly. Rooms are cozy and decorated with traditional antique furnishings, heavy drapes, and bold brocade wallpaper in some. Pop down to the Victorian-styled bar for an aperitif, or linger over an espresso with a good read in the hushed garden.

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.