Custom Cultural Italy Tour in 2 Weeks

A 14 day trip to Italy 
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822 reviews

Italy is like a great masterpiece waiting to dazzle the viewer. On first impression, she amazes you with her beauty. Upon a closer look, her details and history enrapture you—as you’re awestruck by the ruins of Rome, the majesty of the Vatican and the surreal waterways in Venice. Finally, you leave changed forever by the magic of this incomparable place. We invite you to indulge in the enchanting experiences that await you in this itinerary as well as our carefully selected collection of Italy tours on Zicasso.

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Most tours are customized for private travel.

General Information

Boats on the Grand Canal in Venice, Italy.
Milan Cathedral in Piazza del Duomo, Italy.
Early morning mist across fields in Tuscany.
Montepulciano is a medieval and Renaissance town in Tuscany.
Vineyards in the Tuscan region of Chianti.
Detailed Itinerary

Places Visited 

Rome-Florence-Siena-San Gimignano-Chianti-Venice-Milan

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1 - Welcome to Italy! (Arrive in Rome)

When you arrive in Rome, your driver will be waiting for you at the airport to take you to your hotel. Relish the fact that you’re in one of the world’s most amazing cities. Start exploring the city by wandering the ancient streets just beyond your hotel to get your bearings and get into the local culture. When in Rome, do as the Romans do! Soak up the sun at an outdoor café with an espresso and stroll through the piazza while savoring gelato. For dinner, take a walk over to the Piazza Navona, with its hopping nightlife, illuminated fountains, street performers and sidewalk musicians. The piazza is ringed with restaurants and their tables sprawl out into the piazza, making it easy to find an osteria serving traditional Roman cuisine. Try the simple dish of cacio e pepe (pasta with pecorino romano sheep cheese and black pepper), or enjoy the classic spaghetti alla carbonara

What’s Included: transfer from airport, hotel accommodations

Day 2 - Walking Tours of the Roman Forum and Famous Monuments (Rome)

Your tour of ancient Rome begins at the Colosseum, where your guide will share tales of gladiators, mock sea-battles and executions. The tour then leads you through the highlights of the Roman Forum and ends at the altar of Julius Caesar, where visitors still leave flowers and candles today to remember the slain emperor. Stroll through picturesque cobblestone alleyways and discover the enchanting sites, such as the Piazza del Popolo, the Pantheon, the Trevi Fountain and the Spanish Steps. Next, stop at the Campo de’ Fiori, Rome’s most popular outdoor marketplace, and finally enjoy an espresso with a view at Caffarelli Terrace. 

What’s Included: two guided tours, hotel accommodations

Day 3 - Guided Tour of the Vatican City and Leisure Time (Rome)

In the morning, take a tour of Vatican City, and visit the Vatican Museums, which include more than 2,000 rooms of the most extensive collection of art masterpieces in the world. You’ll see Michelangelo’s famous painting on the ceiling of the Sistine Chapel and wander Raphael’s Rooms. Saving the best for last, the tour concludes with a visit to Saint Peter’s Basilica—the largest church on the planet. Some have said that one glimpse has restored their faith. Inside the basilica, you must see Michelangelo’s “La Pietà” sculpture and the Bernini’s cherubs. In the afternoon, you can visit the Borghese Gallery to see world-class Baroque sculpture in a pleasant garden setting. Be sure to stop for a gelato, chat with the locals and people-watch! 

What’s Included: breakfast, Vatican City tour, hotel accommodations

Day 4 - Travel from Rome to Florence - Afternoon Guided Tour of Florence

Take a train ride from Rome to Florence, where you’ll be transferred to your hotel. In the afternoon, you’ll take a guided tour that starts in Fiesole, a hill town of Etruscan origin that today is known for its beautiful viewpoint of Florence. Visit the Franciscan Church of Santa Croce, which houses the tombs of Michelangelo, Machiavelli, Galileo and Rossini. Then return to the heart of Florence. Your guide will take you to the Piazza della Signoria and will elaborate on the notable works of sculpture. This piazza is designed for hanging out. The beautiful arched 14th-century Loggia dei Lanzi still provides covered seating for tourists. Explore the history of Renaissance art at the Uffizi Gallery, with masterpieces by Botticelli, Michelangelo, da Vinci and Giotto. 

What’s Included: breakfast, transfers to and from train station, train ride to Florence, guided tour with museum entrance, hotel accommodations

Day 5 - Explore Renaissance Art in Florence

This morning you’ll see Michelangelo’s “David,” sure to be a highlight of your tour. This 17-foot marble sculpture is so lifelike that it leaves you awestruck. The afternoon is yours to explore this well-preserved historic city, known for its art and culture. It’s easy to stroll past some of the highlights. You could start at the Duomo, then visit the Piazza della Signoria, which is filled with famous statues and is a perfect spot for a gelato or cafe stop, people watching or just a break from the scooter-filled chaos of the main streets. Continue along the Arno River as the sun illuminates the palaces lining its banks until you reach the Ponte Vecchio, where you can shop for souvenirs! 

What’s Included: breakfast, guided tour of Accademia museum, hotel accommodations

Day 6 - Full-Day Excursion in Charming Tuscany (Siena, San Gimignano and Monteriggioni)

Begin your tour with a drive through the rolling green hills of the Tuscan countryside. Arrive at one of Italy’s prettiest medieval towns: Siena. Through a maze of narrow streets, tour the old city center, admiring the magnificent palaces until you reach the Siena Cathedral. You’ll end up at the Piazza del Campo, location of the famous Palio horse races, and nearby you can find an osteria offering traditional cuisine. Next stop is San Gimignano, known as the “City of Towers.” Here you can see the “Annunciation” by Ghirlandaio. Finally visit Monteriggioni, a medieval hilltop town that’s still completely encircled by fortified high walls. Return to Florence for dinner on your own and be sure to try the local specialty, hearty ribolitta soup. 

What’s Included: breakfast, all-day guided tour, hotel accommodations

Day 7 - Leisure Time in Florence and Excursion to Pisa

After breakfast, you’ll have free time to enjoy Florence in the morning. You could visit the Palazzo Vecchio, an impressive palace that was once home to the Medici family. You could also just go shopping; Florence is full of artisan workshops that create handcrafted leather goods and beautiful old-fashioned stationery. In the afternoon, you’ll travel through the picturesque Tuscan countryside to the historic university city of Pisa. The city is famous for its architectural wonders. Enjoy a guided walking tour of Piazza dei Miracoli, where you’ll see the celebrated Leaning Tower, the Pisa Baptistery and other important monuments. Then take a look inside the cathedral, an unrivaled masterpiece of Romanesque architecture, which was constructed between the 11th and 12th centuries. If you’re interested, you can take a pleasant walk with your tour guide to Piazza dei Cavalieri. Here you can admire the historic Scuola Normale, one of the most famous universities in the world. 

What’s Included: breakfast, excursion to Pisa including guided tour, hotel accommodations

Day 8 - Wine-Tasting in the Chianti Region

Enjoy a private tour through the Chianti countryside, the picturesque region that extends from Florence to Siena and is world-famous for its red wines. After a short drive through the green rolling hills, you’ll reach a magnificent castle. Here you’ll visit the vineyards and take a tour of the cellar filled with barrels of Chianti Classico wine. You’ll be offered a snack and a sampling of Chianti wines. In time for dinner, take a drive to a charming medieval village in the hills for a hearty meal at a traditional trattoria. The magical romantic atmosphere will take you back to another era. 

What’s Included: breakfast, guided tour of Chianti region and vineyard wine tasting, dinner including wine, hotel accommodations.

Day 9 - Travel from Florence to Venice

After breakfast, take the train to Venice. Known as “La Serenissima,” which translates to “the most serene.” It’s a city that defies description, and her beauty can only be appreciated in person. The moment you arrive, you’ll feel that you’ve been swept away to another world. With its medieval layout and not a car in sight, Venice lends itself to random wandering and pedestrian discovery. Getting lost is all part of the fun! See where each turn takes you, and you’ll be pleasantly surprised by the hidden passageways, decorative footbridges, Renaissance piazzas and ornate Baroque churches. 

What’s Included: breakfasts, transfers to and from train stations, train ride, hotel accommodations

Day 10 - Discover Glorious Art and Culture (Venice)

Take a guided tour of Venice’s must-see sights, beginning at St. Mark’s Square, which is filled with historic buildings, elegant cafes and classical music. Visit the Byzantine-style St. Mark’s Basilica, decorated with exquisitely detailed mosaics. Next you’ll see the seat of Venetian government for 400 years. With its gorgeous marble facade, the Doge’s Palace is a historical landmark that houses Tiepolo’s famous Neptune painting. Learn about the fascinating history of Piombi Prison and the Bridge of Sighs. Stroll through quiet neighborhoods, and enjoy a refreshing gelato in a secluded piazza. Hop on a gondola for a 40-minute joyride down the most beautiful “main street” in the world: the Grand Canal. 

What’s Included: breakfast, guided tour of Venice sights, hotel accommodations

Day 11 - Tour the Lagoon Islands and Enjoy Classical Opera (Venice)

After breakfast sail into the Venetian Lagoon, departing near St Mark’s Square. You’ll visit four different islands, each intriguing in its own way. Begin at the dreamy San Giorgio Maggiore Island, and visit the church designed by Palladio, with its classical exterior and brilliant Tintoretto art inside. Next stop is the famous glass-making island of Murano. Continue onto the island of Burano, a sleepy fishing community famous for its lace production, as well as its colorful cottages.From there, sail to Torcello to see its Church of Santa Fosca. Tonight you’ll take in highbrow culture at the glorious Palazzo Barbarigo Minotto facing the Grand Canal. Afterwards enjoy a traditional Venetian meal like risotto nero (risotto in squid ink). 

What’s Included: breakfast, lagoon tour, opera concert, hotel accommodations

Day 12 - Travel from Venice to Milan

After breakfast and a morning of exploring Venice on your own, take the train to Milan. Your driver will pick you up at the train station and transfer you to your hotel. In this bustling city, you’ll feel the energy of an international capital. For every church in Rome, there is a bank in Milan. Amidst this vibrant milieu of bankers, publicists and haute couture shops are the impeccably dressed locals who dine on designer-label power lunches. See the magnificent Duomo cathedral, Europe’s third-largest church. Wander the winding side streets just to the north where you’ll find charming neighborhood apartments with gated courtyards and floral balconies. 

What’s Included: transfers to and from train stations, train ride, hotel accommodations

Day 13 - From Medieval Wonders to Leonardo’s Last Supper (Milan)

After breakfast, enjoy a guided tour of the city’s highlights. See Europe’s most prestigious music hall, La Scala, and learn about its fascinating history. Next, stroll through the Galleria Vittorio Emanuele to check out designer shops and stop for espresso at Zucca, an elegant cafe that opened in 1867. By special appointment, you’ll see Leonardo da Vinci’s "The Last Supper" painting. For lunch, why not join the fashion elite at Dolce & Gabbana’s Gold Restaurant? 

What’s Included: breakfast, guided tour of Milan, hotel accommodations

Day 14 - Depart Milan for the U.S.

After breakfast, take a private transfer to Malpensa airport and for your return flight to the U.S. Arrivederci, Italia! 

What’s Included: transfer to airport


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.