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 6194 verified traveler reviews.

Italy Vacation Review: 12 Days

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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Italy Vacation Review: Sorrento, Amalfi Coast, Florence, Tuscany, 10-Night Trip

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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Italy Trip Review: Florence, Tuscany, Rome, Food Tour, Wine Tasting, 1 Week

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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Italy Trip Review: Rome, Florence, Vatican, Sistine Chapel, Colosseum, 2 Weeks

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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Italy Trip Review: Piedmont, Langhe, Turin, Lake Como, 2 Weeks

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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Italy Travel Review: Amalfi Coast, 1 Week

The details provided by Zicasso's travel company were excellent.

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