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36,726 Travelers rated Italy highly for Historical Buildings and Cathedrals

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Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!

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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 vacation 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

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.

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.

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.

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.

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.

*Savings based on all holiday package bookings with Flight + Hotel on Orbitz.com from January through December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

* Prices reflect the lowest "base rate" found over the next 30 days. Rates are subject to change and may not include taxes and fees, hotel service charges, extra person charges, or incidentals, such as room service. All rates are displayed in USD unless otherwise noted. Converted rates are provided for your convenience. They are based on today's exchange rate, but the hotel will charge you in the local currency.