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Overlooking a postcard-perfect Venetian street (a former canal, now paved over) in the artistic Dorsoduro district, this 500-year-old merchant’s townhouse has been revamped as the boutique hotel Ca’Pisani. Behind the traditional exterior lies a modern den with clean lines and sharp, geometric forms that’s enhanced by original work from one of Italy’s most notable Futurist artists, Fortunato Depero. Architects Roberto Luigi Canovaro and Pierluigi Pescolderung balanced original design elements—exposed beam ceilings, brickwork—with 1930s touches, including one-of-a-kind inlay door designs and custom masonry and marble work.

Gaze out at the city’s rooftops from the hotel’s roof terrace, or mingle with locals over wine or an espresso at the street-level café. With the Peggy Guggenheim collection and the Gallerie dell’Accademia gallery just a stroll away, you’ll be able to journey from 16^th-century Venice to the 20^th century all in a few famous paintings.

If you are in the San Lorenzo market area around lunchtime, this little enoteca (wine bar) with its old-fashioned, wood-paneled interior is a good place to stop off for a glass of wine and a sandwich or crostino. It’s usually standing room only, but the choice of wines is great and it’s got a buzzy, local feel to it. There’s a great, well-priced selection of wines to go too.

This family-run bakery has been making cantucci (what you might know as biscotti) for decades. The clan’s patriarch, Roberto, mixes and rolls everything by hand in the back, using a recipe that he knows by heart—ask, and he will happily show you the original recipe, now splattered with egg whites and cocoa. Roberto’s delicate cantucci are far from the tooth-cracking kind sold at many places. If you are really lucky, a fresh batch of the dark-chocolate-and-pistachio variety may have just been pulled out of the oven when you arrive.

Built on the foundations of a 16th century fortification, the Museo delle Culture del Mondo is housed in the 19th century Castello D’Albertis - the private home of the global traveler and collector of antiquities. Veer off the standard art/church museum trail, and up the massive staircase to the Castello, to see a beautifully preserved piece of Genovese history (and some super fascinating collections of global interest). While the walk is quite the hike, the view from the top floor library of the museum is stunning.

Founded in the 9th century, Santa Maria della Scala was one of Europe’s first hospitals. It was also one of the first hospitals anywhere to disinfect its equipment and only stopped taking in patients in the 1980s. (The writer Italo Calvino died here in 1961.) The early history of the hospital is illustrated in the 15th-century frescoes decorating the walls of the Pilgrim’s Hall, and there is a fascinating archaeological museum housed in the labyrinthine basement rooms.

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.

Controlled by the François Pinault Foundation, the same trust in charge of Christie’s auction house, this is a museum-worthy gallery in the heart of Venice. Set inside a 17th-century customs house, it showcases Pinault’s impressive private collection, comprised of some 2,500 pieces of modern art. The location, at the point of land where the Grand Canal meets the Giudecca Canal, is equally spectacular. After you’ve finished browsing the art collection, grab a pastry or a small bite at the in-house Dogana Cafe.

Paszkowski’s historic interior was originally founded in 1848 in what is now Piazza della Repubblica in the center of Florence. A great place to stop for a hot chocolate, espresso, or one of the cafe’s beautiful sweet treats, Paszkowski not only reflects the city’s history but also is a place where fancy locals still gather.

A hotel with the words “gallery” and “art” in its name would be remiss not to include at least a nod to the art world in its decor (though more than a few establishments have been known to throw up a wall-sized painting by a well-known artist and declare themselves art hotels). As Florence’s pioneering design hotel, the Gallery Hotel Art doesn’t skimp. Virtually the entire ground floor, from the lobby through to the lounge and trendy Japanese-Mediterranean-Peruvian fusion restaurant, is one giant gallery, its sleek white decor acting as the calming, understated counterpart to the contemporary art and photography not often found in this city.

Indeed, don’t underestimate the groundbreaking nature of this hotel. Design hotels may be a dime a dozen these days, but when the Ferragamo family’s Lungarno hotel collection launched with this modern getaway designed by Michele Bönan, its clean-lined furnishings and chrome, white, and natural wood hues were a challenge to a city outfitted in rich brocades and dark wood antiques. As such, the Gallery Hotel Art isn’t the flashiest stay, but it is the kind of place you can relax and unwind and feel like you aren’t living in the Renaissance days.

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.”

On a cool night in November, walking alone from an outdoor food market in the center of Florence, I decided to indulge my sweet tooth yet again. I stopped for a “snack,” one that I would never eat just before dinner back home yet couldn’t get enough of in Florence...gelato. Eating gelato, with its creamy texture and multitude of vibrant flavors, is certainly one of the food highlights of being in Italy. Florence has plenty of excellent gelato shops, or gelaterie. Perché no! was my favorite choice because of its convenient location right in the historic center, between Piazza della Signoria and Piazza della Repubblica, and because of its flavors. This combination of persimmon and dark chocolate made eating gelato outside in the cold just before dinner seem perfectly normal.

This intimate, 110-seat restaurant has been hailed as one of the West Village’s true gems since it opened in 2008, both due to the chef’s fresh take on classic Italian cuisine and the inviting ambiance the cozy, dimly-lit eatery exudes. An open kitchen grants diners front-row seats to a culinary production with a rotating cast of fresh pastas starring tagliatelle, orecchiette, and garganelli. Seafood also features prominently in the form of charred octopus, roasted cod, scallops or Arctic char. Oenophiles will delight in the extensive list of Italian wines by region, including an impressive 2,500-bottle cellar that also plays host to private dinners. Just be sure and save room for dessert; the buttery olive oil cake flies out of the kitchen every dinner. Don’t have time to make it down to L’Artusi for dinner? The weekend brunch menu is equally divine.

Artisanal Cornucopia is both art space and concept store, curated entirely by owner Elif Sallorenzo. Sallorenzo has an eclectic eye for design and fashion, and introduces Rome to pieces by established designers like Aquazzura to emerging, one-of-a-kind artisans like Giulia Barela and Benedetta Bruzziches. Her shop has a “salon” vibe: You’ll want to spend time getting to know Sallorenzo in the hopes that she’ll impart her some of her innate sense on you, or just give you straight-forward suggestions.

While few in number, Milan‘s canals can be charming. Naviglio Grande, the largest, is my favorite to walk along. Lined by shops, outdoor cafes and bars, there is life alongside the water anytime of day. If you’re lucky you’ll catch the Antique Market that fills up the walkways on some Sundays. It is a treasure trove of pottery, jewelry, vintage designer clothes, and Murano glass—Milanese have impeccable taste for both the old and new.

A local favorite on postcard-pretty Piazza della Passera in the Oltrarno neighborhood, Il Magazzino serves up delicious Florentine food with a special emphasis on offal. If you are up for it, there’s no better place to sample stalwarts of the indigenous cuisine in dishes such as grilled udder or classic trippa alla fiorentina, or tripe stewed in a tomato sauce topped with grated Parmesan. If offal’s not your thing, opt instead for the mouthwatering linguine with kale pesto. The great wine list offers some affordable choices.