Piazza dei Miracoli complex with the Leaning Tower of Pisa in Italy
30,000+ Verified Traveler Reviews

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

Young girl wearing carnival mask in Venice, Italy

10 Day Trip IdeaFrom $4,500

Wonders of Italy Family-Friendly Tour: Rome, Florence, Venice and More

Rome, Lucca, Florence, Venice, Assisi +11 more
Tuscany, Italy.

9 Day Trip IdeaFrom $4,100

Family Exploration of Italy's Historic Cities & Enchanting Countryside

Venice, Tuscany, Florence, Chianti, Siena +3 more
The ruins of Pompeii in Italy.

12 Day Trip IdeaFrom $5,400

Family Trip to Italy: Nature, Ancient Temples, and Cuisine

Rome, Agrigento, Taormina, Amalfi
Mom and daughter admire the view of Florence from Piazzale Michelangelo

7 Day Trip IdeaFrom $3,200

One Week Family Vacation to Tuscany and Cinque Terre

Florence, Lucca, Riomaggiore
Venice, Italy.

7 Day Trip IdeaFrom $3,200

Amazing Family Italian Vacation in 7 Days: Rome, Venice, and Florence

Venice, Florence, Rome
San Pietro in Valle Abbey in Valnerina, Umbria, Italy.

9 Day Trip IdeaFrom $4,100

Italy Family Vacation for First Timers

Rome, Florence, Umbrian Countryside, Perugia, Turin +1 more

How Zicasso Works

Here's how we create life-enriching, luxury travel experiences

  1. 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. 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. 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.

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Positano, Italy

10 Day Trip IdeaFrom $4,500

Italy Family Vacation: Coastline, History, and Food

Sorrento, Pompeii, Positano, Rome, Florence +2 more
Gondola ride near the Rialto Bridge on the Grand Canal in Venice, Italy

10 Day Trip IdeaFrom $4,500

Cultural Exploration Family Tour of Northern Italy

Venice, Bolzano, Milan, Padua, Verona

14 Day Trip IdeaFrom $6,300

Ultimate Two-Week Family Vacation to Southern Italy

Naples, Pompeii, Sorrento, Amalfi, Positano +3 more
Family at La Punta Spartivento in Bellagio, Lake Como, Italy

8 Day Trip IdeaFrom $3,600

Family Friendly Lake Como Vacation

Milan, Como, Lenno, Bellagio
Tram with Arco della Pace in the background, Milan, Italy

7 Day Trip IdeaFrom $3,200

One Week Milan Family Vacation

Milan, Como
Family on a luxury yacht in Sardinia, Italy.

16 Day Trip IdeaFrom $15,600

Luxury Italy Family Vacation

Milan, Venice, Sardinia, Bologna, Florence +3 more

4.9

Reviews of Zicasso's Multi-Generational Italy Vacations & Tours

Based on 6228 verified traveler reviews.

Italy Tour Review: 12 Days

It was the trip of a lifetime! Zicasso’s travel agent was absolutely incredible and took care of every detail. He went above and beyond in many ways, and didn't think twice about it. In the middle of the trip, we asked to switch our final destination. He didn't hesitate and had everything taken care of within two hours. I will definitely refer this travel company to anyone planning a trip to Italy.

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Italy Tour Review: Sorrento, Venice, Colosseum, Blue Grotto, Gondola Ride, 2 Weeks

Zicasso’s travel agent developed our itinerary to our specifications. She reached out right away and called if a follow-up was needed or to clarify something. Our trip went off without any problems. The itinerary was very clear, as was the timeline, trip summary, and tickets. If I had a question, she always responded.

We had one slight issue, which was quickly resolved and worked itself out. I communicated often with her throughout the trip and I always received a pleasant response. Our trip was designed to our needs. Our accommodations were wonderful! I would definitely recommend this travel company!

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France, Italy, China, Japan Trip Review: Paris, Rome, Hong Kong, Tokyo, Glass Blowing, Cultural Experiences, 16 Days

Zicasso’s travel company did such a great job putting the trip together. I was charged for an extra night at our hotel in Paris, but they are refunding that and the Cairo portion of the trip we had to cancel.

Our Paris tour guide was great and I’d recommend her to anyone. Our Rome tour guides were very good. Hong Kong was fine. Our Tokyo guide was wonderful.

Really, the only hiccup on the trip was our hotel in Hong Kong. The company that picked us up dropped us at one hotel, not the correct one. Thankfully, a couple of their bellhops walked us and all our luggage several blocks to the correct hotel. Our tour guide the next day also went to the wrong hotel, but we only lost about 45 minutes before we figured out the issue. If you use that hotel again, please make sure folks know which hotel is which.

The "Fast and Furious" car experience was OK; however, my grandson was so tired he slept through most of it. The chopstick-making was fun, as was the glass-blowing experience.

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Italy Trip Review: Tuscany, Florence, Lucca, Cinque Terre, Chianti, Cooking Class, Biking, Hiking, Local Cuisine, 1 Week

Zicasso’s travel agent was accommodating and helpful for our trip to Tuscany. Since there were so many of us, people had different needs. She was able to accommodate our differences and work out plans the best she could. We enjoyed all of the selections that she gave us, especially the dinner in the Chianti vineyard. Everyone loved that. We definitely recommend this travel company!

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Italy Trip Review: 11 Days

It was a spectacular trip, tailored to our preferences and executed perfectly by Zicasso's travel company!

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Italy Honeymoon Review: Rome, Florence, Tuscany, Venice, Wineries, History, 12-Day Trip

Our honeymoon trip to Italy, planned by Zicasso’s travel company, was the perfect trip in every way. From the time we landed in Rome and were greeted by our driver to the time we left Venice 12 days later, every detail was taken care of. The guides, tours, accommodations, restaurant recommendations, and travel transfers were expertly executed, so we didn't have to worry about anything except having the time of our lives!

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