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36726 Travelers rated Italy highly for Historical Buildings and Cathedrals

Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
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Book a package and join the 188 others who’ve received 100% off their flights this year!

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).

Things to do in Italy


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.


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.


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.


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.


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.


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.


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.


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.


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.


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.

Insider tips for Italy travel

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.

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.

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 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.

Top Rated Hotels for your Italy Vacation

Hotel Abbazia
Hotel Abbazia
3.0 out of 5.0 Cannaregio, Calle Priuli Cavaletti 68, Venice, VE
Free Cancellation
4.6/5 (14 reviews)

All was perfect clean,helpful and kind staff ........

Reviewed on Jan 1, 2020
Guests staying at Hotel Abbazia enjoy free WiFi in public areas, free newspapers, and a TV in a common area. The 24-hour front desk has multilingual staff ready ...
Le Sirenuse
Le Sirenuse
5.0 out of 5.0 Via Cristoforo Colombo 30, Positano, SA
5.0/5 (2 reviews)

From the moment we arrived in the driveway to this hotel, we were made to feel like family! This privately owned hotel is an absolute gem. The staff is friendly and sincere; the property is immaculate and the furnishings are gorgeous, including some really spectacular art. We loved everything about ...

Reviewed on Apr 25, 2018
Guests staying at Le Sirenuse enjoy access to a full-service spa, a fitness center, and a rooftop terrace. If you drive, self parking is EUR 60.00 per night, ...
Air Rooms Rome Airport by HelloSky
Air Rooms Rome Airport by HelloSky
4.0 out of 5.0 Via Generale Felice Santini, 1023, Aeroporto Inter. Leonardo da Vinci, Fiumicino
Free Cancellation
4.3/5 (31 reviews)

Clean and convenient Comfy beds Fantastic staff Perfect for when you miss your flight and need to stay close to your early morning flight.

Reviewed on Dec 2, 2019
Guests of Air Rooms Rome Airport by HelloSky enjoy free WiFi in public areas, a business center, and free newspapers. The 24-hour front desk has multilingual ...

^Savings based on all package bookings with Flight + Hotel made on from January 1, 2019 to December 31, 2019 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.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.