
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 6201 verified traveler reviews.
It was a great experience! Every activity was fun and interesting. The guides and drivers were wonderful. You made our trip so easy.
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Everything went perfectly. We had such a good time. All our tour guides were expert historians. All the car pick-ups and trains went smoothly. We added a last-minute tour in another city and Zicasso's travel specialists were so accommodating. I highly recommend them.
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My wife and I recently returned from our first trip to Italy and want to highly recommend Zicasso's travel specialist and her company for creating the perfect vacation for us. It was a two-month process of back and forth, but no matter what we asked of her, she delivered several options.
We had a perfect mix of historical Florence and its museums, and wonderful restaurants, and the Tuscany and Umbria countryside experience. And on our first day, when our flight into Florence got diverted to Milan, we had the peace of mind that our travel specialist was there to help with her much appreciated support.
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Working with Zicasso’s travel specialist and the team was easy and wonderful. Our group enjoyed all of our excursions and tours. The drivers and guides were all wonderful, kind, and informative. Our arrangements for staying were clean, accessible, in great locations, and with incredibly friendly staff. The daily reminders were perfect and the few times we had questions, the response was timely and helpful.
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From start to finish, this was an amazing trip! All the accommodations were excellent, the tour guides were knowledgeable and engaging, our drivers were friendly and helpful, and the experiences (walking food tours, cooking class, wine tastings) were just what we wanted! We are extremely happy with the help we received from Zicasso's travel specialists, all the arrangements that were made, the communication throughout our stay—the entire trip!
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We loved our itinerary! We gave the locations we wanted to visit to Zicasso’s tour operator and they fit everything in. They were with us every step of the way and listened to feedback about any adjustments, and stayed within budget.
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