
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 6082 verified traveler reviews.
We had a wonderful experience, from planning our trip with Zicasso's travel designer to experiencing all Italy had to offer. She and her team worked with us when we needed to have them step in on hotel accommodations at our beach resort.
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The hotels were in great locations within the city to be able to walk and see all the sites. The drivers we had were very professional and courteous. I would have liked to have a better platform to track the trip and the destinations. I have used a trip plans app before and it’s easy to use. I felt like the communication with our travel guide was minimal, but our overall trip was beautiful and memorable, and we will definitely be traveling again soon.
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Zicasso's travel designer listened to our desires and implemented those wishes. The trip was flawless. The accommodations, transportation, and guides were spot-on and within budget. We will certainly use the travel company for future trips.
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This was a superb trip that allowed us to combine personal visits to Taormina and Syracuse with a pre-planned group meeting in Catania. Planning and communication were excellent, supported by an app that let us easily view our itinerary, complete with phone numbers for the drivers, hotels, and the tour operator contacts.
The hotels were perfect! They were wonderfully located, with impeccable service in Taormina and Syracuse. Our excursions were private and diverse, and allowed us to combine culture, foodie interests, and free time. The guides were top-notch, knowledgeable, and flexible.
We especially loved seeing the smaller towns of Sicily; Militello, Ragusa, Aci Castello, and Modica. We even arrived in one small town during their annual festival.
We had a dedicated driver for our trip who was, himself, a treasure; always on time, always ready to adjust to changes, and a delightful personality.
This was such a good experience that we have selected Zicasso's tour operator to book another Italy trip next year.
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This was a girls' trip of a lifetime! It was perfect from the start of planning until the end of the trip. Zicasso's travel experts were so flexible in planning and giving options. The experiences were all so unique, special, and local. We would never have been able to create this on our own. Also, during the trip, they were available 24/7 for any recommendations or help. I cannot say enough good things! This is my second time using Zicasso and I have told all my friends!
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We received great communication from Zicasso's travel specialist and wonderful hotel, tours, transportation, and guide arrangements.
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