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 5962 reviews.

Italy Trip Review: Rome, Amalfi, Positano, 12 Days

The trip Zicasso's travel specialist arranged for us exceeded all our expectations. It was absolutely wonderful; not a single detail was overlooked. The hotels were excellent, the tours were great, and the drivers were always on time. I totally recommend Zicasso and the agency, and will undoubtedly use them for future travel plans.

Reviewed By Philip S.

Italy Travel Review: Lake Como, Ostuni, Private Boat Tour,...

Zicasso's travel designer did a terrific job. We had the initial phone consult, after which she delivered a first draft of the itinerary. From there, she helped guide us through a few revisions until we got the details smoothed out. We are experienced travelers and can appreciate a well-constructed trip, and that's what our experience with our agent reflected.

One crucial thing is that all the drivers who are engaged to move you around are prompt. Every one of them was right on time and friendly and helpful to boot. It was much appreciated.

To sum up our experience, I would do it all again with Zicasso and the agency and our agent. Our trip to Italy in the late summer of 2025 was something we will not soon forget!

Reviewed By tony B.

Italy Tour Review: Calabria, 11 Nights

Zicasso's travel partner is very thorough and makes sure the trip is tailored to your vision. They are flexible and very responsive. We would recommend them to anyone traveling.

Reviewed By Evan C.

Italy Tour Review: Vatican, Colosseum, Roman Forum, Pompeii,...

Zicasso's travel agency far exceeded our expectations. We had our five-year-old and 11-year-old children with us, so the tour guides and walking needed to be kid-friendly.

Our hotel in Rome was wonderful, the location was perfect, and they had good A/C and a breakfast buffet. There were plenty of great restaurants within easy walking distance, as well as the Vatican.

Our tour guide for the Colosseum and Roman Forum was great. Pompeii was amazing. Our tour guide was basically a celebrity down there and knew exactly how to take us around the ruins without ever waiting.

Tuscany was our favorite by far. We did a cheese-making experience and lunch that was super-cool. The kids got to play with the farm animals and the owners were so attentive and interesting. We did a cooking class with a chef that was the kids' favorite thing on the entire trip. I would make a point to book this experience; the kids still talk about it and wear the aprons around the house. The resort in Tuscany was nice. We had our own private pool, plus the resort pool, and could easily walk to a small local town with some great food.

Venice was good, but probably our least favorite on the trip. You have to walk a ton, which was difficult for the kids, but it's still worth experiencing.

We travel a bunch and I would highly recommend using Zicasso's travel partner.

Reviewed By Kevin S.

Italy Travel Review: Dolomites, 2 Weeks

Zicasso's travel designer made the whole trip run very smoothly. It was a pleasure working with her.

Reviewed By Joseph B.

Italy Vacation Review: E-bike Tour, Kayaking, 10-Night Trip...

This was the best trip ever!!! I am so grateful Zicasso introduced us to our tour operator. This team was amazing! They set up a call to learn more about us and jumped into action. Within a short time, they came back to us with a presentation on ideas, with recommendations. There is no chance our trip would have been half as good without them. They even had a text group on standby while we were here in case we needed anything.

Reviewed By Linda C.