Piazza dei Miracoli complex with the Leaning Tower of Pisa in Italy
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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

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

Based on 2354 verified traveler reviews.