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 $170

1 NH Collection Firenze Porta Rossa

4 stars
4.4 / 5 14 reviews

Via Porta Rossa,19 Map

Book in advance and save 10%

The NH Porta Rossa Hotel was build in the 12th century and maintains the elegant architecture for which Florence is so famous. The beautiful entrance gives way to the magnificent interior. The staff at the NH Porta Rossa Hotel is attentive and on hand to assist with... More

Hotel only $68

2 NH Napoli Ambassador

4 stars
4.0 / 5 2 reviews

Via Medina 70, Map

Free late check-out on Sunday (until 5 p.m.).

NH Ambassador is set in the historic center of Naples and with its 30 floors gives guests the possibility to admire the spectacular view of both the historic city and the Gulf. Located near the Royal Palace, San Carlo Theatre, the shops of Corso Umberto I and Molo... More

Hotel only $192

3 NH Collection Milano President

4 stars
4.2 / 5 9 reviews

Largo Augusto, 10 Map

Free late check-out on Sunday (until 5 p.m.)

Offering sleek accommodations conveniently situated in the heart of the city and close to the business district and famous area attractions, NH President Hotel Milan makes for an ideal starting point for corporate and recreational travelers in the financial city of Italy.... More

Hotel only $111

4 Bella Venezia Hotel Venice

4 stars
3.6 / 5 59 reviews

Calle dei fabbri 4701/11 Map

Special 10% Off MID WEEK

The sixteenth century palace in which Hotel Bella Venezia is sited in, has been completely respected and restored in accord with the Italian Belle Arti. The works, ended by the middle of year 2006, have gifted back the ancient splendour to each Venetian bedrooms, rooms... More

Hotel only $108

5 Mecenate Palace Hotel Rome

4 stars
4.2 / 5 151 reviews

Via Carlo Alberto 3 Map

Free Wi-Fi is available in all areas

The Mecenate Palace Hotel Rome comprises two adjacent buildings: the one by Rinaldi overlooking Piazza Santa Maria Maggiore dates from 1887; the other on via Carlo Alberto was built a few years later. Renovation work was carefully planned to restore the building's faades... More

Hotel only $231

6 Firenze Number Nine Hotel and SPA

4 stars
4.7 / 5 9 reviews

Via Dei Conti 9 Map

Firenze Number Nine, located in the centre Florence, famous world-wide as the jewel of the Renaissance, is a unique hotel in terms of attention to detail and warm hospitality. It sits adjacent to the Medici Chapels, a few steps from the Cathedral, the Ponte Vecchio and... More

Hotel only $106

7 Royal Continental Hotel Naples

4 stars
2.7 / 5 9 reviews

Via Partenope 38/44 Map

Modern hotel set on Naples seafront overlooking the enchanting Bay of Naples, cartel Dell ovc fortress. The 400air conditioned guestrooms feature light dcor with wood furnishing: all include cable TV and WI-FI in common areas, Guest can work out in the gym and enjoy a dip... More

Hotel only $117

8 NH Milano Machiavelli

4 stars
4.5 / 5 10 reviews

Via Lazzaretto, 5 Map

Buffet Breakfast included and Free WI-FI

The four-star NH Machiavelli is set in Milan city center between the metro station of Porta Venezia (line 1) and Repubblica (line 3). The property position is perfect both for business travelers and tourists. In fact, metro line 1 connects the city center to the Fiera... More

Hotel only $166

9 Bellini Boscolo Hotel Venice

4 stars
4.0 / 5 62 reviews

Lista Di Spagna 116 / A Map

Book in Advance & Save

An 18th century patrician palazzo, the Bellini Boscolo Hotel Venice was transformed into a hotel at the turn of the last century. Overlooking the Grand Canal in Venice’s Cannaregio district, this elegant hotel is a short walk from St. Mark’s Square at the heart of the... More

Hotel only $120

10 Starhotels Michelangelo Hotel Rome

4 stars
4.0 / 5 44 reviews

Via Della Stazione Di S. Pietro, 14 Map

Save 10% - Stay 2 nights

A sunny lobby lounge with brocade sofas and marble floors ushers guests into Starhotels Michelangelo Rome, which sits in the heart of baroque Rome along the ancient walls of Vatican City. A candlelit piano bar with button-tufted leather couches and mirrored walls is... 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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