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

Multi-Generational Italy Vacations & Tours

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...

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.

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

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

Why Travelers Choose Us

Benefits of Using Zicasso

Plan Your Trip with
Top Travel Specialists
We connect you with the best boutique tour companies to plan your dream trip.
Your Itinerary Tailor-Made
Just for You
Travel with a personalized itinerary and experiences designed for you.
Travel Worry-Free
Every Time
24/7 support and local assistance for every moment of your vacation.
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

Reviews of Zicasso's Referral Service

4.9 stars based on 5660 reviews.

Italy, Greece Honeymoon Review: Culture, Cuisine, Snorkeling,...

My husband and I went through Zicasso to plan our honeymoon to Italy and Greece. This was the best decision ever! We worked closely with our travel specialist to plan our trip and she was absolutely phenomenal. This was our first international trip outside of the US, so we were a bit nervous at first! However, our specialist ensured every aspect of the trip was organized and that we were taken care of every step of the way.

The biggest relief was transportation. We did not have to give a second thought as to how we were getting places; we had drivers set up at every destination and for nearly every activity. Also, we had 24/7 support if anything were to go wrong, which gave us peace of mind.

If you are hesitant to use Zicasso for your next trip, I want you to know that I was too, but it was the best decision! We were able to personalize and tailor our trip to our needs without the hassle of dealing with the details.

Reviewed By Grace B.

Italy, Malta Trip Review: City Tour, 20 Days

I was very pleased with the entire planning of the trip. The communication with Zicasso's tour company was excellent. The meals that were pre-arranged by them were fantastic and we probably would not have found them on our own.

Reviewed By komal P.

Italy, France Travel Review: Scenery, 10-Day Trip

The trip was amazing all around. Incredible. The service and itinerary were perfect. We highly recommend Zicasso's travel company.

Reviewed By Mitch A.

Greece, Italy Travel Review: Rome, Athens, Santorini, Local...

Our trip was absolutely amazing! This was the trip of a lifetime. Zicasso and our trip planner were incredible. He was repeatedly helpful, offering personalized attention to our needs. He booked amazing tours for us and seemed to really grasp what we wanted. Everything was incredible.

Reviewed By Helena H.

Italy Vacation Review: Ravenna, Padua, History, Art, Scrovegni...

It was a great pleasure working with Zicasso's tour agency. Our travel designer and her staff were attentive to the kind of trip we wanted and planned a great itinerary. The hotels, restaurants, and drivers were all top-notch. For us, the acid test was the quality of the guides, and they excelled there as well. We would happily have them plan another trip for us.

Reviewed By Robert K.

Italy Tour Review: Ravenna, Verona, Rimini, Scrovegni Chapel,...

My husband and I had a great time on our trip to the northeast Adriatic Coast of Italy. We have very specific tastes as far as where we like to stay and the private tours we like to have during the trip. Zicasso's travel company did a great job, giving us fantastic hotels, and all of our tour guides were top-notch.

Reviewed By Danielle S.