This unique itinerary that starts in the elegant city of Milan and ends in the historic city of Rome features several of Italy's famous highlights as well as off-the-beaten-path destinations such as Modena and a few cities in the Umbria region including Perugia and Orvieto. Designed to accommodate the needs of a large family with diverse interests, the following travel package features a variety of activities including visits to the Autodromo of Monza, the Chocolate Museum in Perugia, the Basilica of St. Francis in Assisi and the Vatican Museums in Rome. Like all Trips 2 Italy vacations, leisure time is built into the package to ensure that your family has plenty of opportunities to explore these fascinating destinations independently as well. Continue reading below to discover several of Italy's most captivating locales and then contact Trips 2 Italy to start planning your ideal family vacation to Italy; our travel specialists are accustomed to working with families of all sizes and will ensure the itinerary for your once-in-a-lifetime vacation exceeds everyone's expectations.
DAY 1: DEPART USA
Board your flight and travel to the incredible city of Milan.
DAY 2: MILAN
Upon arrival in Italy, collect your checked luggage and travel to your hotel in Milan via private car transfer. Your hotel will be located in the historical city center within walking distance of major monuments as well as museums, restaurants and shops. After checking into the hotel, the remainder of your afternoon will be at leisure to begin your independent exploration of the city center. In the evening, enjoy your first taste of Milan’s cuisine during a family dinner at a historic restaurant. Afterwards, return to your hotel for an overnight stay.
DAY 3: MILAN, MONZA, ARESE
Your first full day in Italy will begin at the Basilica of Santa Maria delle Grazie for a tour of Leonardo da Vinci’s breathtaking painting, The Last Supper. This world-renowned fresco depicts the moment Jesus Christ divulged that one of his disciples would betray him. A close inspection of this intricately detailed fresco of the late fifteenth century is captivating and inspires a deep feeling of reverence.
After admiring the beauty of The Last Supper, we suggest you explore the surrounding area at your leisure and enjoy lunch. Later, embark on a group walking tour to the historical center of the city to discover the gorgeous La Scala Theater, the Galleria of Vittorio Emanuele II, and a rooftop view from the Duomo terrace.
Alternatively, some members of your family may prefer to spend an afternoon outside of Milan and take a tour of the Autodromo of Monza. This historic racetrack is just north of the city and is the home of The Formula One Italian Grand Prix. Then, travel just a half hour away to the fascinating and historical Alfa Romeo Museum in Arese. Six floors of the museum brilliantly showcase the history, technology, and style of this extraordinary automobile brand. Channel your inner James Bond as you check out these magnificent vehicles and grab a photo opp or two. Then it is back to your lodging area for dinner and an evening stroll for your last night in Milan.
DAY 4: MODENA AND PERUGIA
Rise and shine and you’ll be off to the lovely city center of Modena for a few hours of leisure. This enchanting town is full of stunning medieval architecture in the form of a splendid main cathedral and a two hundred ninety foot tall bell tower that is located in the Piazza Grande. These structures are so rich in tradition, art, and history that Modena has been designated as a UNESCO World Heritage Site. You may also wish to visit the Enzo Ferrari Museum, which showcases the life’s work of the famous sports car founder. After you have enjoyed this historical walk through the city center, treat yourself to a leisurely lunch featuring Modena’s renowned specialty: Balsamic Vinegar. When you finish lunch, continue onto Perugia, where you will check into your next hotel. Take a moment to freshen up, then enjoy your first taste of the local cuisine during dinner at a historic restaurant.
DAY 5: PERUGIA
If you think this Italian vacation sounds sweet so far, the best is still yet to come. Go lightly when eating breakfast as you will want to have plenty of room left when you visit the Perugina House of Chocolate. This guided tour takes you through roughly a century of history and quality associated with the Italian craft of making chocolate. The very best part of the visit is the taste testing opportunities that abound at the conclusion of the tour.
If you’re not too full from all that delicious chocolate, grab a bite of lunch and consider visiting one of the city’s beautiful open-air squares to soak up the local culture. Late in the afternoon, take a private walking tour of Perugia to see some of the most visited landmarks including the Duomo and Rocca Palatina. End your day dining on homemade Italian delicacies and sipping a glass of fine wine before returning to your hotel for a restful night.
DAY 6: ASSISI
Lace up your shoes and prepare for a day excursion to the nearby city of Assisi. This area is full of gorgeous, historical churches and is known as the town of St. Francis. Upon arrival, you will enjoy a private walking tour of this city’s major historical highlights.
The most famous sight of course is the enormous and world-renowned Basilica of San Francesco where you can admire the amazing frescoes by Giotto. Other must-sees include the Temple of Minerva, whose columns are estimated to be two thousand years old, the Basilica of Santa Chiara, which was built using stone from nearby Mount Subasio, the striking Cathedral of San Rufino and the Basilica of Santa Maria degli Angeli where St. Francis spent much of his time. Pace yourself and do not rush through these amazing structures full of art and history. To get the most out of your touring experience, it is sometimes best to split your sightseeing into two parts, before and after lunch.
End the day by making the short ride back to your lodging for a relaxing dinner and a delightful evening walk through the area.
DAY 7: UMBRIA COUNTRYSIDE
After a few days of sightseeing the many wonders of Perugia and Assisi, it will be time to enjoy the simple offerings of the rolling Umbrian countryside. Although not as well-known compared to its cousin Tuscany, Umbria is possibly one of the best areas for taking a wine tour.
Enjoy a prearranged wine tasting tour through the region that will take you to several different wineries. Here, visitors can explore the grounds, see how wine is made, and finally enjoy a wine tasting. The wine tasting tour will wrap up with just enough time for you to return to your hotel and enjoy one last magical dinner and evening in the city of Perugia.
DAY 8: ORVIETO AND ROME
After breakfast, catch a few winks or just enjoy the scenery as you travel an hour or so south to the charming town of Orvieto. This quaint town has a historic part of the city that sits atop a picturesque hill offering stunning views of the more modern city below.
Enjoy a leisurely excursion through the city to experience lovely countryside views, gardens, parks and the historical Duomo di Orvieto, which is considered to have one of the most beautiful facades in Italy. With so much to see and do, it can be tempting to skip lunch, but don’t as you will need your energy for afternoon adventures. Thrill seekers may enjoy climbing the two hundred plus steps of the Tower of Moro and exploring the partially hidden Pozzo della Cava cave network.
If you can manage to tear yourself away from the loveliness of Orvieto, you will continue south for another hour before reaching your final destination of Rome. What better way is there to end your day than enjoying a delightful Italian meal at a cozy table on the streets of Rome?
DAY 9: ROME
Get an early start to your day so you don’t miss a thing in this fabulous city. Begin with a guided tour of the world-renowned Roman Colosseum. The tour allows visitors to see and explore the above ground and underground areas of the Colosseum. The underground section of the arena is particularly fascinating for children who can trace the steps of past gladiators. Guests will also tour the Roman Forum, the once center of ancient Rome.
If you wish to enjoy more sightseeing after lunch, an optional guided excursion to the archeological ruins of Pompeii may be arranged. Lose yourself as you wander the ancient streets of Pompeii and catch a glimpse of the plaster casts of those killed in the eruption of Mount Vesuvius years ago.
Be sure to leave enough time to treat yourself to a leisurely dinner at a renowned local restaurant after a long day of sightseeing. Then enjoy a walk around the city after dark for a completely different view of how the city sparkles at night.
DAY 10: VATICAN
No stay in Rome is complete without a guided tour of the Vatican and its many rich museums, the precious Sistine Chapel, Saint Peter’s Basilica, and Saint Peter’s Square. These religious landmarks are said to be simply captivating even to those who are not religious. Your expert local guide will lead you through many of the notable highlights and provide historical context for the wonders you admire. After the tour, enjoy a nice lunch at a historic trattoria or osteria.
The rest of the afternoon is yours to finish up some last minute sightseeing or partake in souvenir shopping. In the evening, we recommend a final dinner at one of the best restaurants in Rome with your family. Do not miss this opportunity to toast to your memorable vacation!
DAY 11: RETURN HOME
Your heart will likely be full of warm memories of your time with family in the beautiful country of Italy as you depart for home. The long flight home is a fabulous time to get a head start on planning your next trip back. Arrivederci!

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PACKAGE START AT $3,204.00 INCLUDES:
• Roundtrip flights in economy class with in-flight meals, drinks, and entertainment. (*)
• 2 Nights accommodation in a premium 4 star HOTEL in Milan. (**)
• 4 Nights accommodation in a premium 4 star HOTEL in Perugia. (**)
• 3 Nights accommodation in a premium 4 star HOTEL in Rome. (**)
• 9 Daily Buffet Breakfast at your Hotel.
• 8 Private Tours as per Itinerary.
• Ground Transfer from/to Airport.
• Transportation as per itinerary with Private Driver .
• Vat Taxes and Service Charges (in Italy) included.
WHAT IS NOT INCLUDED:
• U.S. & Foreign Departure Taxes and Surcharges Fee(s) assessed by the Airlines.
• Hospitality city tax which varies by city and hotel category. Where applicable, it must be paid locally at the hotel.
• All which is not listed under “PACKAGE INCLUDES”
(**) Rate based on two adult persons sharing a double or twin bedded room with private bathroom. Single rooms are available at an additional supplement. Children’s, triple room rates and alternative accommodation arrangements are available upon request. (Additional and different charges may apply).
For additional information about Milan, Modena, Perugia, Assisi, Rome Other hotels, and destinations are available. Please don’t hesitate to ask our Trips 2 Italy travel assistants.
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Italian Family Vacations, 11 Days, Assisi, Cathedrals, Churches and Monuments, Milan, Natural Landmarks, Rome, Umbria, Vatican, Wine Tasting