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.

Learn More
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 6178 verified traveler reviews.

Italy, Switzerland Travel Review: Livigno, St Moritz, Winter Olympics, 11 Nights

First time to the Olympics and an add-on to Switzerland! Zicasso’s travel specialist was great at listening to our needs and putting together an itinerary.

Our trip to Livigno was fantastic! The location to the two Olympic venues was ideal.

All of the details were covered and when we had a change in one of our day tours due to potential avalanches, the team at the travel company was extremely responsive and was able to adjust.

All of our transportation was well organized and on time. We also had to pivot when our flights home to the US were changed due to weather and the team quickly helped with adjustments to our schedule.

We loved the train from Italy to Switzerland.

We highly recommend this travel specialist and the travel company!

See more

Italy Vacation Review: Vatican City, Colosseum, Florence, 1 Week

We had great hotel and tour picks.

See more

Italy, Switzerland Travel Review: Livigno, Milan, St Moritz, Pasta Cooking Class, 'The Last Supper', 14 Days

Our experience with Zicasso’s travel company was simply outstanding! Our travel specialists provided top-notch service, from the initial planning to the entirety of the trip.

They were able to secure housing for us in Livigno during the Olympics when no one else was able to do so. Responsiveness to our inquiries during the planning process was always prompt and thorough. Communication regarding the next day's agenda throughout the trip was excellent, including the contact information for our drivers and tour guides, tickets for events, and links to Google Maps, with directions, when needed. If we could give them more than five stars, we would!

See more

Italy Trip Review: Pisa, Accademia Gallery, 5 Days

We had a great trip. It was logistically perfect. The hotels were great and the guides were exceptional.

See more

Italy Travel Review: Sorrento, Taormina, Rome, Pompeii, Mount Etna, Wine Tasting, 2 Weeks

We had a fabulous trip to Italy, including to Sorrento, Taormina, and Rome. Zicasso’s travel specialist made sure every detail was taken care of, including stays in beautiful, well-located hotels and excursions that were interesting and fun for our family.

For example, she arranged for an airport host to assist us with our arrival to and departure from the Rome airport, and she was simply amazing, whisking us through the airport and eliminating stress for our family.

See more

England, Italy Vacation Review: London, Rome, 3 Weeks

In all respects, a well-planned and well-executed trip to London and Rome. The guides were exceptional in knowledge, kindness, and sense of humor. The best restaurant recommendation was the one in London.

See more