
Multi-Generational Italy Vacations & Tours
Italy is the perfect place to experience old and new, culture and discovery as a family exploring with multiple generations. Train like gladiators before visiting the drama of the Roman Colosseum. Embrace the beauty of the Sistine Chapel while hunting for hidden images often overlooked by visitors. Delight in the flavors of famous Italian dishes while learning to cook traditional recipes together. Whether actively discovering ancient treasures or relaxing with a view of the Tyrrhenian Sea, find inspiration for your perfect multi-generational Italy family trip with our sample itineraries below.
Explore Our Trip Ideas
Let these itineraries inspire your personalized travel experience

10 Day Trip IdeaFrom $4,500
Wonders of Italy Family-Friendly Tour: Rome, Florence, Venice and More

9 Day Trip IdeaFrom $4,100
Family Exploration of Italy's Historic Cities & Enchanting Countryside

12 Day Trip IdeaFrom $5,400
Family Trip to Italy: Nature, Ancient Temples, and Cuisine

7 Day Trip IdeaFrom $3,200
One Week Family Vacation to Tuscany and Cinque Terre

7 Day Trip IdeaFrom $3,200
Amazing Family Italian Vacation in 7 Days: Rome, Venice, and Florence

9 Day Trip IdeaFrom $4,100
Italy Family Vacation for First Timers
How Zicasso Works
Here's how we create life-enriching, luxury travel experiences
1.Share Your Travel Dreams
Zicasso specializes in custom tours, vacations, and safaris tailored to your interests and preferences. From private African safaris to culinary experiences in Europe, submit a trip request to share your ideas and travel style.
2.Meet Your Travel Specialists
To ensure a personalized experience, we'll carefully handpick and introduce you to two of our top travel specialists, each with unsurpassed destination knowledge and local insight aligned to your luxury travel dreams.
3.Design Your Perfect Journey
Compare the expertise of two specialists with itineraries crafted exclusively for you. You can refine these further and choose your preferred proposal. Our unique process ensures a more creative, personalized, and expertly crafted trip.

10 Day Trip IdeaFrom $4,500
Italy Family Vacation: Coastline, History, and Food

10 Day Trip IdeaFrom $4,500
Cultural Exploration Family Tour of Northern Italy

14 Day Trip IdeaFrom $6,300
Ultimate Two-Week Family Vacation to Southern Italy

16 Day Trip IdeaFrom $15,600
Luxury Italy Family Vacation
Reviews of Zicasso's Multi-Generational Italy Vacations & Tours
Based on 6194 verified traveler reviews.
It was a fantastic trip. Everything we planned with Zicasso’s travel company was on time and with high-quality local guides and drivers. They were very responsive and helped us build an itinerary for our 12-day trip to southern Italy. They stayed in touch throughout the planning process, helping us find restaurants and answer questions. I would highly recommend this travel company to anyone planning a trip to Italy.
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Zicasso’s travel specialist was a pleasure to work with. She helped me plan our trip of a lifetime to Italy. I told her which cities we wanted to visit and our interests, and she gave me great recommendations for tours and experiences. She was flexible with the itinerary changes I made beforehand and, after our arrival, the pre-arranged transportation was seamless and the hotels were great.
Our ambassador during the trip was very responsive when I had questions. I appreciated the daily messaging app reminders for the times and activities for the next day, including a location link on Google Maps for the meeting points. Our pre-arranged drivers and tour guides were excellent.
This holiday was everything I hoped for. If I am fortunate enough to plan another holiday to Italy, I will definitely use the travel company again! Based on this experience, I will definitely use Zicasso again for an international holiday.
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We had a great trip to Florence, Tuscany, and Rome. One of the best parts about the trip was our travel company. Zicasso's travel specialist took care of booking everything we needed and doing so within budget. I didn't have to worry about keeping up with tour tickets and schedules because he had already taken care of all that. He was also available for quick questions and updates while we were on our trip. We couldn't have asked for better!
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Zicasso set us up with a wonderful travel agent. The process of choosing and communicating through the Zicasso system was easy and helpful.
The travel specialist and her team planned a wonderful 15-day trip, with nine days in Rome and four days in Florence. She found us great accommodations that included a kitchen, which was a must for us. Other travel agents were not able to provide such accommodations.
The drivers we had were professional and picked us up on time. The guides were experts in their field and generally had taught at universities. The guides were very personable and tailored the tours to our interests.
She arranged all the necessary skip-the-line tours. We went to the Vatican with three different tours: the Sistine Chapel, the Gardens, and the necropolis to see St. Peter's tomb.
There were a couple of hiccups in this perfectly planned itinerary. Each time, the travel specialist and her staff were immediately available and guided us through solutions, such as trying to get to the Colosseum during the Roman Marathon.
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Zicasso’s travel company was highly responsive and understanding of what we wanted to experience and used their expertise to steer us to the best people and locations possible.
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The details provided by Zicasso's travel company were excellent.
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