Italy Vacations

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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.

  • 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).

  • 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.

Italy Vacation Packages

Hotel only $262

1 NH Collection Firenze Porta Rossa

4 stars
4.4 / 5 12 reviews

Via Porta Rossa,19 Map

Book in advance and save 10%

NH Collection Firenze Porta Rossa was built in the 12th century and represents one of the oldest hotels in Italy. When it has been refurbished, all furniture have been carefully chosen and the original frescos have been saved. The property incorporates the Monalda Tower,... More

Hotel only $75

2 Majestic Hotel Naples

4 stars
4.3 / 5 3 reviews

Largo Vasto a Chiaia, 68 Map

Situato nel cuore di Napoli, accanto alla zona marittima e circondato da alcuni dei negozi pi esclusivi della citt, l'Hotel Majestic costituisce un'eccellente opzione di soggiorno. Indicato specialmente per coloro che ricercano la faccia pi dinamica di Napoli e ugualmente... More

Hotel only $126

3 Grand Hotel Puccini Milan

4 stars
3.8 / 5 21 reviews

Corso Buenos Aires, 33 Map

Easy Metro and train access from convenient Milan business hotelThe Grand Hotel Puccini is a Corso Buenos Aires hotel that functions as a base for exploring one of the most captivating historical European cities, Milan, Italy. Business and sightseeing travelers from all... More

Hotel only $195

4 Starhotels Splendid Venice

4 stars
4.3 / 5 32 reviews

San Marco Mercerie, 760 Map

Stay 2 Nights or more & Save

Float up to contemporary comfort in a 16th century Venice innNestled in the heart of historic Venice between St. Mark's Square and the Rialto Bridge, the Starhotels Splendid Venice's building has hosted guests since the 16th century. Fully renovated in 2007, the... More

Hotel only $153

5 Starhotels Metropole Hotel Rome

4 stars
4.0 / 5 42 reviews

Via Principe Amedeo, 3 Map

Stay 3 Nights & Save 20% Off

Elegant Rome hotel in city centerIn the heart of Rome and steps from Termini Station and the Opera House, guests encounter sophisticated decor and modern amenities at the Starhotels Michelangelo Rome. A lobby piano bar and lounge with silk-cushioned wicker wingback chairs... More

Hotel only $132

6 Centrale Hotel Florence

3 stars
4.3 / 5 24 reviews

Via dei Conti 3 Map

Florence Center Hotel is completely restructured and renovated. Situated in the heart of Florence, Florence Center Hotel is just a few steps away from the Duomo and the principal monuments of the City, a short distance from the central Train Station S. Maria Novella, from... More

Hotel only $114

7 Piazza Bellini Naples

3 stars
4.6 / 5 9 reviews

Via Santa Maria di Costantinopoli, 101 Map

Save 10% Non Refundable

Opened in April 2007 and recently expanded and renovated, the hotel is located in a XVI century building, in the heart of Naples' historical cent-re. It's a few minutes' walk from the main subway lines it is very close to the main tourist attractions, museums,... More

Hotel only $125

8 Starhotels Anderson Milan

4 stars
4.0 / 5 14 reviews

Piazza Luigi Di Savoia 20 Map


Conveniently situated in the heart of Milan, immediately by the central railway station, this newly refurbished hotel offers contemporary amenities in amid metropolitan chic. Rooms offer a charming yet functional atmosphere, for the combination business and leisure.... More

Hotel only $199

9 Carlton On The Grand Canal Hotel Venice

4 stars
3.9 / 5 55 reviews

Santa Croce, 578 Map

Best Rate

Luxury hotel’s 100 windows overlook Grand Canal in Venetian styleThe Carlton On The Grand Canal Hotel Venice features 100 windows that overlook the Grand Canal, where gondolas float by along Venice's main thoroughfare. Inside, guests enjoy... More

Hotel only $142

10 Mecenate Palace Hotel Rome

4 stars
4.1 / 5 139 reviews

Via Carlo Alberto 3 Map

Free Wi-Fi is available in all areas

The Mecenate Palace Hotel in Rome offers 4-star luxury accommodations in an authentic 19th century Palazzo, styled with floral decor, Neo-Classical pillars, and curved marble staircases perfect for dashing down in an elegant gown. Dine directly beneath the night sky in... More

  • 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.

  • Tuscany

    Salute wine country. Wander medieval towns (Siena, San Gimignano, Monteriggioni) where art galleries, cathedrals and trattorias are edged in rolling vineyards. Soak in therapeutic hot mud baths or go rafting at Marmore Falls. Visit the Leaning Tower of Pisa or the Isola d'Elba to swim in the azure-blue sea.

  • 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.

  • 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.

  • 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.

  • Rome

    Peer into the gladiator and toga worlds of the Roman Forum and Colosseum. See the sun spill onto the Pantheon's marble floors, and toss coins into the Trevi Fountain. Climb the Spanish Steps, and drink grappa in Campo de'Fiori. Explore Vatican City's spiritual and artistic treasury: St. Peter's Basilica, the Vatican Museums and the Sistine Chapel.

  • 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.

  • 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.

  • 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.

  • 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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