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Active from the 13th to 15th centuries and considered an influence on the pre-Renaissance movement, the Sienese School of painting is identifiable by its themes—always religious, and usually with a focus on Biblical miracles—and its signature style, a dreamy mix of Roman, Gothic, and Byzantine influences that often feature dazzling gold backgrounds. Opened in 1932, this museum boasts one of the world’s largest collections of Sienese School works, as well as a number of Renaissance and late-medieval pieces from Italian artists. Wander through the impressive building—a combination of two 14th- and 15th-century noblemen’s palazzi—to find works like Duccio’s Madonna and Child, Michelino da Besozzo’s Mystical Marriage of Saint Catherine (celebrating the “calling” of Siena’s native daughter), and Bartolo di Fredi’s expansive Adoration of the Magi. Paired with a visit to Florence’s Uffizi, coming here offers insight into the differences—and longtime rivalry—between the two cities.

One of the most fun places I dined at in Italy was Il Latini, in Florence. It’s in a large, maze-like building with aged prosciutto hanging from the ceilings, and art collaged upon the walls. Seating is at communal tables, and at times it felt like we were all at a wedding. In our case, my boyfriend and I sat with another couple from Australia, who were beginning their tour of Italy, but it’s easy to meet locals at this spot, too. The waiters and the owner are very persuasive when it comes to traditional Florentine food. I requested half of a Florentine steak, but I am sure I was given a full one—one of the largest I have ever seen served. It was cooked rare, and was extremely tender and flavorful. However, I am not much of a carnivore, and as such, my favorite part of the dinner was the fresh sage ravioli. After our meal, the waiter kept bringing shots and wine, which appeared to be on the house. There are no exact prices, and the waiter determines your meal’s cost.

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.

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.

Cesare al Casaletto is far off the well-beaten tourist track, but it is easy to get to: just take the 8 tram from Piazza Venezia or Largo Argentina and get off at the very last stop. Fifty yards from the tram tracks sits Rome‘s best trattoria, where spectacular fried appetizers (get them all, or at least the gnocchi fritti and polpette di bollito) give way to classic pasta dishes like carbonara and gricia. The second courses are excellent and fall-off-the-tailbone braised oxtail is a favorite. Pair it all with fairly priced natural wines from all over Italy and be sure to leave room for dessert, preferably the panna cotta.

You can’t visit Florence without indulging in ice cream once at the very least, but it’s not so easy to find the real deal. Carapina, gelateria of choice for cognoscenti (but often overlooked by tourists), is located a stone’s throw from the Ponte Vecchio, brain child of Simone Bonin who is widely acknowledged to be one of the best ice cream makers in Italy. Sixteen flavors are available at any one time and produced in small batches each day from top-notch local, strictly seasonal ingredients. Classics include pistachio, ‘real’ yoghurt and the bitterest of bitter chocolate but there are more unusual flavors too like the sweet/salty gorgonzola, Parmigiano reggiano or creamy mozzarella di bufala.

Every Saturday and Sunday on Via S. Teodoro, tucked just off Circus Maximus, Rome‘s best farmer’s market takes place. It’s run by Campagna Amica, an Italy-wide organization that promotes local, sustainable agriculture—so all of the products sold here, from jam to olive oil, bread to cheese, beer to wine, come from the Lazio region only, and are sold directly by the producers themselves. Tastings are a-plenty and the producers are more than happy to chitchat about their foodstuffs. If you come around lunchtime, you can buy a cheap lunch—maybe even including porchetta sliced right off the pig, like here—to eat on the picnic tables outside.

The first Tasmanian winery to achieve biodynamic certification has a new restaurant and tasting room that doubles as a biodynamic wine information center. Sample limited-edition bottles such as the Settebello single-block pinot noir at the cellar door, or order your favorite vintage alongside a rustic Italian dinner at farm-to-table Osteria.

On a promontory within Bouddi National Park, overlooking a secluded bay and a short walk to an empty rust-red beach, Pretty Beach House lives up to its (classically understated Aussie) name. It’s hard to believe this intimate retreat is only a 90-minute drive from Sydney city center. Its location is spectacular and historic—spot the 2,000-year-old Aboriginal rock drawings on a nature walk nearby.

There are four guest pavilions, each outfitted with wood-burning fireplaces, deep-soaking clawfoot tubs, and sun-drenched decks overlooking Broken Bay and Angophora treetops (three have their own private plunge pools). Dining is included in the stay, and it’s exceptional: Celebrated chef Dean Jones takes freshly caught seafood and local produce and crafts them into modern Australian dishes, which you can enjoy anytime you like in the Beach House’s safari-chic dining room or poolside beneath the shady gums.

This unassuming two-story plaza has become a popular Friday- and Saturday-night hangout for 20- and 30-something locals. In addition to its shops, Plaza Paseo Cobá is home to several restaurants and bars with a trendy, bohemian vibe that’s far removed from the beach area’s bump and grind. Feast on artisanal Italian at indoor-outdoor Casa Sofia, or dance to live music at the Public Place.

No need to jet to France for French bistro fare—holding court a stone’s throw from the famed 9th street Italian market, French husband-and-wife duo Charlotte and Pierre Calmels (formerly of Le Bec Fin fame) regale locals at Bibou with a masterful, market-driven menu that changes at the chef’s whim. A must on any visit to the City of Brotherly Love!

Luxury and opulence define Donatella Versace’s fashion sense. This Roman-style palace with Brazilian marble, Italian mosaics, and gold columns, is no departure from her aesthetic. Details from the custom bath products to gold-and-fuchsia-patterned upholstery were conceived by the designer. From $492. 61/(0) 7-5509-8000. This appeared in the September, 2012 issue.

Dario Cecchini is the most famous butcher in Italy and is probably the only one who recites Dante while carving up his carcasses. His small shop on the outskirts of the medieval village of Panzano is a Mecca for carnivores seeking quality meat (plus curious tourists), and he also has a restaurant—Solociccia—where you can sample some of the best bistecca in the region. If you visit his Antica Maccelleria Cecchini on a Sunday morning, when he works to a background track of jazz and opera, you’ll be offered a glass of wine, a hunk of pecorino cheese, and a nibble of some of his meaty products (like the fennel-flavoured salami called ‘finocchiona’) to ease the waiting time.

JK Place Firenze is a far cry from Florence’s obsession with all things Renaissance. Set amid the buzz of Piazza di Santa Maria Novella, this onetime private mansion is decked out in black, white, peach, gray, and chrome, with inflections of 1950s movie stars, 1970s pop art, and ornate 19th-century architecture. The reception feels like a library, and the breakfast room is a glassed-over former courtyard with a hefty antique wooden communal table. Free drinks, fresh fruit, and homemade treats (and bubbles at cocktail hour) can be found at all hours in the guests-only lounge area. Impress your well-heeled friends by inviting them to dine on the piazza terrace, presided over by the appropriately black-and-white Basilica di Santa Maria Novella, before moving downstairs to the clubby J.K. Pink Room. Slip upstairs to your individually designed room for a divine night’s sleep, then awake ready to take on one of the world’s most historic cities.

The rooftop terrace bar of the smart Rinascente department store offers some of the most stunning views in the city and the in-your-face views of the Duomo from up here really help to put Brunelleschi’s monumental creation into perspective. It just about makes up for the not-very-exciting selection of drinks, snacks and light meals that make up the menu. Beware that you pay more to eat and drink on the terrace than inside the bar.