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Piazza dei Miracoli complex with the Leaning Tower of Pisa in Italy
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Multi-Generational Italy Vacations & Tours

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Ratings of Zicasso's Service
<p>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.</p>

Italy is the perfect place to experience old and new, culture and discovery as...

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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.

Help Me Plan My Trip

Life-Enriching Travel Designed Just for You

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    Trips curated by the world’s top destination experts

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    Concierge-level service leading up to and during your trip

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    Unique, exclusive experiences and insider access

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Ratings of Zicasso's Service
Young girl wearing carnival mask in Venice, Italy

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

Places Visited: Rome, Lucca +14 more
Places Visited: Rome, Lucca, Florence, Venice, Assisi +11 more

10 Day Custom Tour

From $4,500

Piazza Venezia in Rome, Italy

Family Exploration of Italy's Historic Cities & Enchanting Countryside

Places Visited: Venice, Tuscany +6 more
Places Visited: Venice, Tuscany, Florence, Chianti, Siena +3 more

9 Day Custom Tour

From $4,100

The ruins of Pompeii in Italy.

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

Places Visited: Rome, Agrigento +2 more
Places Visited: Rome, Agrigento, Taormina, Amalfi 

12 Day Custom Tour

From $5,400

Mom and daughter admire the view of Florence from Piazzale Michelangelo

One Week Family Vacation to Tuscany and Cinque Terre

Places Visited: Florence, Lucca +1 more
Places Visited: Florence, Lucca, Riomaggiore 

7 Day Custom Tour

From $3,200

Ponte Vecchio bridge at sunrise, Italy, Florence

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

Places Visited: Venice, Florence +1 more
Places Visited: Venice, Florence, Rome 

7 Day Custom Tour

From $3,200

Umbrian Hills in the Midday Sun, Italy

Italy Family Vacation for First Timers

Places Visited: Rome, Florence +4 more
Places Visited: Rome, Florence, Umbrian Countryside, Perugia, Turin +1 more

9 Day Custom Tour

From $4,100

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Positano, Italy

Italy Family Vacation: Coastline, History, and Food

Places Visited: Sorrento, Pompeii +5 more
Places Visited: Sorrento, Pompeii, Positano, Rome, Florence +2 more

10 Day Custom Tour

From $4,500

Gondola ride near the Rialto Bridge on the Grand Canal in Venice, Italy

Cultural Exploration Family Tour of Northern Italy

Places Visited: Venice, Bolzano +3 more
Places Visited: Venice, Bolzano, Milan, Padua, Verona 

10 Day Custom Tour

From $4,500

Ultimate Two-Week Family Vacation to Southern Italy

Places Visited: Naples, Pompeii +6 more
Places Visited: Naples, Pompeii, Sorrento, Amalfi, Positano +3 more

14 Day Custom Tour

From $6,300

Family at La Punta Spartivento in Bellagio, Lake Como, Italy

Family Friendly Lake Como Vacation

Places Visited: Milan, Como +2 more
Places Visited: Milan, Como, Lenno, Bellagio 

8 Day Custom Tour

From $3,600

Tram with Arco della Pace in the background, Milan, Italy

One Week Milan Family Vacation

Places Visited: Milan, Como 
Places Visited: Milan, Como 

7 Day Custom Tour

From $3,200

Bologna, Italy

Luxury Italy Family Vacation

Places Visited: Milan, Venice +6 more
Places Visited: Milan, Venice, Sardinia, Bologna, Florence +3 more

16 Day Custom Tour

From $15,600

Life-Enriching Travel Designed Just for You

  1. 1

    Trips curated by the world’s top destination experts

  2. 2

    Concierge-level service leading up to and during your trip

  3. 3

    Unique, exclusive experiences and insider access

Help Me Plan My Trip

Zicasso in the News

New York TimesWall Street JournalTravel + LeisureCNN

Reviews of Zicasso's Referral Service

4.9 stars based on 5841 reviews.

Review: Luxury Italy Vacation, Milan, Lake Como, Cinque...

"Our agent worked carefully with us from the beginning to get the right mix of independent travel and guided travel during our trip."

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Reviewed By Larry H.

Travel Review: Luxury Italy Vacation, Rome, Venice, Florence,...

"The trip that this travel agency organized for my husband and I to visit Italy ended up being my dream vacation."

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Reviewed By Meredith F.

Travel Review: Italy Family Vacation, Rome Venice, Florence,...

"It was everything we hoped for and so much more. Our agent listened to my desires and hit every one and even some I didn't know I wanted!"

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Reviewed By Jennifer C.

Italy Tour Review: Rome, Florence, Pisa, Cinque Terre, Lake...

"This travel company was incredible and is a highly recommended company, as is Zicasso."

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Reviewed By Duane M.

Italy Tour Review: Rome, Florence, Tuscany, Cinque Terre,...

"In general, the trip was fantastic! I worked with a Zicasso tour operator to create a trip and she came through with a terrific itinerary."

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Reviewed By Thomas B.

Italy Luxury Travel Review: Cinque Terre, Florence, Milan,...

"Our trip was wonderful and one of the best we've done over the years!"

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Reviewed By debra G.

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