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Experience Your Best Italy Vacation

Ciao bella! Sink your teeth into the Italian experience, from the cannoli and Bocca della Verita to the Courmayeur ski resorts. Linger on the beaches of Sicily and Sardinia, or wander through medieval hilltop towns in Tuscany. Shop your way across Milan, and find frescoed beauty and flying buttresses in the Vatican, Umbria and Sienna. Fill your glass with limoncello in Naples, and write postcards in the Piazza della Signoria in Florence. Drink cappuccino in Rome, and toss coins in the Trevi Fountain.

Whether it's a pilgrimage to the Sistine Chapel or a honeymoon in Positano, let Orbitz show you the Appian Way. Our insiders highlight the top 10 attractions, the best time to go on an Italy vacation, plus Italy's hidden gems.

Best time to take a trip to Italy

For a more Italian experience, visit between April and June, and late September through October. Beach towns are vibrant and packed throughout summer (especially August), then sleepy and cold from November to February. High season spans across Italy from July through mid-September, with the exception of hot, humid August -- many hotels, shops and restaurants close and Italians head to the coast.

Italy is especially festive with fireworks and pageantry during Holy Week, Easter and Christmas. For a uniquely Italian experience, celebrate the feast days of the city's patron saints: Saint Mark, Venice (April 25), Saint John the Baptist, Florence (June 24) and Saints Peter and Paul, Rome (June 29).

Insider tips for Italy travel

The Palio (Siena)

Experience medieval pageantry living on in the Palio di Siena (July 2 and August 16). Each year, thousands of onlookers watch ten Sienese jockeys race their horses around the Piazza del Campo in honor of the Assumption of Mary.

The Bourbon Street Jazz and Spirit Bar (Naples)

See New Orleans from a Naples perspective. This rugged bar serves cold beer on tap, live jazz and that Big Easy vibe.

Maremma vineyards (Tuscany)

Maremma wines have been causing a stir in the wine world with their experimental grape blends and techniques. Hit the Maremma trails to explore wineries and festivals.

Macerata Opera (Macerata)

Enjoy the open-air opera house Macerata Opera. The structure was built between 1820 and 1829 and is considered to be one of the most highly-renowned neoclassic buildings in Italy.

Book bars (Rome)

Practice your Italian literature with some vino and wordsmiths in a Roman book bar. Find a crop of them in the Travestere (namely, Bibli) and the hip pockets of Mattatoio.

Things to do in Italy

Campania

Visit Naples, Capri, Anacapri and Sorrento, a popular resort town on the Amalfi Coast. Spend time in the cliff-top towns of Amalfi and Positano where pastel buildings hug the coastline. Find the ruins of Emperor Tiberius's villa just east of Capri town.

Florence

Art star Florence draws sculptors, poets and Vespas to its winding streets and rustic piazzas. See Botticelli's goddesses, Giotto's Madonnas, and the etched world of Durer in the Galleria degli Uffizi. Meet the Statue of David, twirl your spaghetti in Oltrarno, and laugh with the satyrs at the Fountain of Neptune. Shop the open-air market near Piaza del Mercato Centrale followed by a night of opera at the Teatro Verdi.

Lombardy

Get sucked in by terrain aglitter with lakes, islands and charming towns. Navigate Lake Maggiore's Borromean Islands, including artistic gem Palazzo Borromeo on Isola Bella. Visit the serene Orta San Giulio on Lago d'Orta, or Lake Como set against the snow-capped Alps. Shake it up with a trip to Gardaland -- the third largest theme park in Europe.

Milan

Ciao Prada, Gucci and Versace! Stock up on Italian gear in the Galleria Vitorrio Emanuele II, one of the world's most upscale shopping malls. Dine by the Stazione Centrale, thin hit the vibrant nightlife in Porta Ticinese, Brera and Navigli.

Naples

Zesty and spiced with gastronomic traditions, bring your appetite to this pizza capitol. Burn calories shopping the Galleria Principe di Napoli, or hiking the dormant Volcano Solfatara. Relive Pompeii history in ancient ruins, and refuel on gelato and limoncello. Visit on St. Joseph's Day (March 19) for a festival filled with zeppole.

Sicily

Swim off the island's golden beaches, and enjoy a bella sera of Malvasia wine and fresh-caught seafood. Climb a rope near the unpredictable Mount Etna -- the largest live volcano in Europe. View the Byzantine mosaics adorning the Palatine Chapel in Palermo.

Umbria

This painterly paradise is home to green meadows, the Apennine Mountains and medieval towns Perugia and Assisi. Swim and sunbathe in Lago di Trasimeno and climb the Rocca Maggiore fortress. Visit the cliff-top town of Orvieto for gnocchi, and marvel the frescoed Duomo di Orvieto.

Venice

Take a gondola through the watery streets of Venice to churches, museums and more. Stroll zigzagging paths dotted with cafes, markets and shops. Snap photos of the Rialto Bridge and see the flurry of pigeons in Piazza San Marco. Visit the famous gardens of Villa Pisani in Stra village, and the shoe museum in Villa Foscarini Rossi.

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