Tour of Italy: Milan, Lake Como, Venice, Tuscany & Rome

A 16 day trip to Italy 
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The birthplace of Michelangelo and Leonardo da Vinci. The civilization that built the Pantheon and the Sistine Chapel. The destination of fashion enthusiasts and religious pilgrims alike. Italy’s history and beauty is endlessly inspiring to every visitor. From the ancient ruins of Rome to the magnificent Renaissance in Florence and surreal decadence in Venice, this tour of Italy promises to astound you.

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General Information

The ruins of the Roman Forum, Rome, Italy.
A gondola transports tourists on the Venice canals in Italy.
House with vibrant flowers hanging on its wall in Tuscany.
A Tuscan villa near Pienza, Italy.
Statue of David by Michelangelo.
Detailed Itinerary

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

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

Upon arrival at Malpensa airport, your private transfer will greet you and take you to your hotel. Begin your tour in the bustling city of Milan, a center of business and fashion. Milan has been a center of prominence since the Middle Ages. You’ll witness medieval grandiosity at the Duomo, the city’s impressive cathedral. This gothic masterpiece seats 10,000 worshipers and is crowned with 140 spires and more than 2,000 statues. In this intriguing metropolis beneath the facade of post-WWII buildings, many surprises await you. 

What’s included: private transfer from the airport; hotel accommodations

Day 2 - From Medieval Wonders to Leonardo’s Last Supper (Milan)

After breakfast, enjoy a guided tour of the city’s highlights. See the world-famous La Scala Opera House and learn about the illustrious history of the Duomo, a marvel of medieval architecture built when Milan was considered the “new Athens.” Stroll through Galleria Vittorio Emanuele, the “parlor” of the city, to check out designer shops and stop for espresso at Zucca, a favorite cafe of Giuseppe Verdi. At the Church of the Santa Maria delle Grazie, you’ll have a chance to see Leonardo da Vinci’s "The Last Supper." The highly protected masterpiece is only viewable by appointment. The rest of the afternoon is at your leisure to visit art galleries or shop at your favorite boutiques, including Armani, Gucci and Prada. 

What’s included: breakfast; guided tour of Milan; hotel accommodations

Day 3 - Experience the Allure of Lake Como

After breakfast at your hotel in Milan, you’ll be transferred to the train station for your train ride to Lake Como. When you arrive, your private transfer will take you from the station to your hotel. Italy’s romantic Lake District lies just north of Milan in the shadow of the Alps. The peaceful Lake District offers the allure of Italy beyond the hustle and bustle, far away from the chaotic Italian tourist experience. Dotted with pretty villages, tiny ports and aristocratic villas in lush gardens, Lake Como has an endearing Old World elegance. You can throw your itinerary to the wind and enjoy an afternoon of compete relaxation! Breathe in the fresh air and commune with nature in this gorgeous alpine setting. Enjoy a picnic lunch in a setting worthy of a Renoir painting, or visit one of the local restaurants serving authentic homemade cuisine. 

What’s included: breakfast; transfers to and from train station; train ride to Lake Como; hotel accommodations

Day 4 - Visit the City of Como and Bellagio Resort (Lake District)

After spending one night in this idyllic setting, wake up refreshed and enjoy breakfast at your hotel. Today you’ll take a private tour of the area, including visits to the villages of Como and Bellagio. Your tour guide will take you through Como’s delightful old town, free of traffic and everyday concerns, where your imagination can step back to another era. Stop to enjoy espresso at one of the town’s charming cafes. Admire the beauty of the lake as you stroll along the promenade and watch ferryboats traverse the serene blue waters. Next visit the resort town of Bellagio, called the “Pearl of the Lake.” This picturesque village is characterized by magnificent villas, centuries-old churches, cobblestone lanes and stairways filled with shops. Stroll around the tiny streets that wind down to the lake and visit a fancy shopping arcade to stop for gelato or espresso. 

What’s included: breakfast; guided tour; hotel accommodations

Day 5 - Travel from Lake Como to Venice

After breakfast, take the train to Venice. Known as “La Serenissima,” which translates to “the most serene,” Venice defies description. Her beauty can only be appreciated in person. You must experience the romance yourself as you traverse the lagoon by gondola or water taxi and while strolling the ancient maze of narrow streets, alleyways and piazzas. With its medieval layout and not a car in sight, Venice lends itself to random wandering and pedestrian discovery. Watch as gondolas glide through hidden canals lined with residential homes, where homemade Italian cooking permeates the air. Stop into a cicchetti bar for a glass of wine with the locals. 

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

Day 6 - Art and Culture Tour of Venice

Your guided tour takes you to Venice’s highlights, starting at St. Mark’s Square. This grand piazza was called “the most beautiful drawing room in Europe” by Napoleon. Visit St. Mark’s Basilica, built in the 11th century and covered with 43,000 square feet of intricately detailed mosaics. Next take a guided tour of the Doge’s Palace, distinguished by its pink and white marble facade. Discover the history of Piombi Prison where prisoners (including Casanova) took their last glimpse of beautiful Venice. Stroll through the charming, winding streets and get lost as you discover beautiful piazzas and forgotten churches. Enjoy a gondola down the scenic Grand Canal. Take in postcard views of Rialto Bridge and impressive palaces from the days when Venice was the richest city. 

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

Day 7 - Tour the Venetian Islands and Enjoy Classical Opera in Venice

Take a magical journey into the Venetian Lagoon, departing after breakfast from the Ponte della Paglia. In this calm section of the Adriatic, you’ll discover four fascinating islands. Begin at the San Giorgio Maggiore Island, where you’ll be wowed by spectacular views of Venice. Next visit Murano, renowned for its glass factories and souvenir shops. Continue onto the island of Burano, famous for lace and colorful cottages. From there, sail across to Torcello, the first settlement in the lagoon. The Church of Santa Fosca is worth a visit just to see the splendid ancient mosaics. In the evening, enjoy an opera or concert at the Palazzo Barbarigo Minotto, a glorious 15th-century palace. We also recommend a romantic candlelit dinner served canal-side. 

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

Day 8 - Travel from Venice to Florence

After breakfast, spend the morning exploring Venice at your leisure. In the afternoon, you’ll take a train ride from Venice to Florence, where you’ll be transferred to your hotel. The rest of the late afternoon is yours to explore this well-preserved historic city, known for its art and culture. The Renaissance began in Florence, wealthy because of its cloth industry, trade and banking. Stroll past some of the highlights. You could start at the Duomo, the city’s neoclassical domed cathedral that is the third largest in Christendom. Then visit the Piazza Signoria for a gelato or espresso stop and continue along the Arno River as the sun illuminates the palaces lining the Arno, until you reach the Ponte Vecchio, the famous bridge lined with gold and silver shops. 

What’s included: breakfast; transfers to and from train station, train ride, hotel accommodations

Day 9 - Explore a Treasure Trove of Renaissance Art (Florence)

Begin your guided tour with a short coach ride to Fiesole. This delightful hill town of overlooks Florence and the Arno Valley, offering the quintessential panoramic view of red-tiled Florentine rooftops and the Duomo in the distance. Then you’ll return to the center of Florence and swing past the impressive Palazzo Vecchio, Florence’s town hall. Sure to be a highlight: Michelangelo’s “David” statue at the Galleria dell'Accademia. Take in the best of Renaissance art at the Uffizi Gallery, and be sure to see Botticelli’s “Venus,” a masterpiece of intricate detail and beauty that takes your breath away. 

What’s included: breakfast; guided tour of Fiesole and Florence including two museum visits

Day 10 - Full-Day Excursion in Charming Tuscany (Siena, San Gimignano and Monteriggioni)

Enjoy a scenic drive through the Tuscan countryside, winding around vineyards and olive trees. Arrive in the medieval city of Siena, an UNESCO World Heritage site. Here you’ll visit the Siena Cathedral with its ornate, gilded interior and star-studded ceilings. For lunch, you can find an osteria offering traditional cuisine, such as homemade pici pasta (thick spaghetti typical of Siena). Visit another UNESCO World Heritage site— San Gimignano, the 13th-century hill town that is filled with art treasures. Finally visit Monteriggioni, a tiny town untouched by modern influence, 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 11 - Leisure Time in the Chianti Region

After breakfast, you’ll enjoy a private transfer to your hotel in Chianti. The entire afternoon is free to explore this beautiful part of the Tuscan countryside. In this idyllic pastoral landscape dotted with medieval hill towns and lined with cypress trees, you’ll have a chance to truly relax and enjoy la dolce far niente, an Italian expression that translates as “the sweetness of doing nothing.” Savor the cuisine, sample the wines and enjoy the peaceful setting. If you’re passionate about Italian cuisine, take a class at the acclaimed Osteria di Passignano cookery school, located in a historic vineyard abbey. Another idea is to visit Montepulciano, a charming hilltop town filled with cantinette (wine-tasting outlets). Wander the medieval streets and sample the famous super-Tuscan wines. 

What’s included: breakfast; transfer to hotel in Chianti; hotel accommodations

Day 12 - 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 an estate winery and then visit one of the most beautiful Romanesque churches in the area, surrounded by greenery and known for its interesting architecture. For dinner, you’ll be treated to a typical hearty Tuscan meal along with fine wines. Enjoy the delicious cuisine and the charm of being far away in Italy. 

What’s included: breakfast; guided tour of Chianti region and vineyard wine tasting; dinner; hotel accommodations.

Day 13 - All Roads Lead to Rome! (Florence to Rome)

After breakfast, take a private transfer to the Florence train station for your train ride to Rome. When you arrive in Rome, your driver will be waiting for you at the train station to take you to your hotel. Relish the fact that you’re in one of the world’s most amazing cities. In the afternoon, explore 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 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 filled with restaurant tables that sprawl out into the piazza so it’s easy to find an osteria that serves authentic Roman cuisine like the simple dish of cacio e pepe (pasta with pecorino romano sheep cheese and black pepper) or the classic spaghetti carbonara. 

What’s included: breakfast; transfers to and from train station; train ride to Rome; hotel accommodations

Day 14 - Walking Tours of the Roman Forum and Famous Monuments (Rome)

Begin your tour at the Arch of Constantine, arrive at Palatine Hill for an awe-inspiring outlook onto the Roman Forum. Then take a walk through the Roman Forum to see the ruins of a great civilization. After a delicious pizza or pasta lunch on your own, enjoy an afternoon walking tour Rome’s most famous squares, monuments, fountains and artists. Visit the Piazza Navona to take in Bernini’s famous “Fountain of the Four Rivers,” a triumphant centerpiece of this lively square. Finish the tour with a coffee stop at Caffarelli Terrace, which offers a splendid perspective of the historic center of Rome. 

What’s included: two guided tours; hotel accommodations

Day 15 - Guided Tour of the Vatican City and Leisure Time (Rome)

In the morning, take a tour of Vatican City. Visit the museums, which include more than 2,000 rooms of the most extensive collection of art masterpieces in the world. You’ll see Michelangelo’s incredible “Creation of Adam” ceiling painting on the Sistine Chapel. Saving the best for last, the tour concludes with a visit to Saint Peter’s Basilica. The basilica’s awe-inspiring scale and ornate decorative details are sure to take your breath away. The afternoon is free for you to explore the city at your leisure. Wander the hidden streets and discover Roman ruins next to contemporary office buildings and immerse yourself in the exciting chaos of the city’s central locations like the Spanish Steps, the perfect place for a gelato stop! 

What’s included: breakfast; Vatican City tour; hotel accommodations

Day 16 - Arrivederci Italia! Depart for the U.S

After breakfast at your hotel, take a private transfer to Fiumicino airport for your return flight to the U.S. Hopefully your coin tossed into the Trevi Fountain will bring you back to Rome soon or for one of the other great tours of Italy!

What’s included: breakfast; 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.