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.

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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

4.9

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

Based on 809 verified traveler reviews.

Italy Trip Review: Taormina, Agrigento, Palermo, 8 Nights

Our Zicasso travel specialist did a fantastic job planning our family vacation for five adults.

Each hotel was top-notch. At the villa in Taormina, the rooms were luxurious, with unbelievable views of the bay and Mount Etna from private verandas. The staff were gracious and the restaurant's breakfast buffet delicious. Lunch and dinner were top-notch. The hotel in Agrigento was modern and the grounds were exceptional. It was close to the Valley of the Temples, with amazing views of the ruins from each room and the beautiful infinity pool. The hotel in Palermo was old-fashioned luxury with up-to-date facilities and close to the old town.

Our tour guides and drivers were excellent.

My only regret is that we only had 10 days to explore Sicily as there was so much more to see!

Our agent did a yeoman's job helping us plan this trip.

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Italy Honeymoon Review: Rome, Sorrento, Florence, Venice, Vineyard, Wine Experience, 11-Night Trip

Zicasso's tour company did a wonderful job of planning our dream honeymoon! Our travel agent took into consideration our wants and wishes, and created half- and full-day activities for us throughout the trip. We were able to visit four locations (Rome, Sorrento, Florence, and Venice) while in Italy. The trip was a perfect mix of relaxation and exploration. The tour company took away the stress of traveling and allowed us to enjoy the days without worries.

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Italy Tour Review: Venice, Tuscany, Rome, Amalfi Coast, Capri, Cooking Class, Ferrari Experience, 2-Week Vacation

We had the best time during our wonder trip to Italy. We explored Venice, Tuscany, Rome, and the Amalfi Coast. Zicasso's travel agency arranged the most beautiful hotels, with exceptional service, and fun and exciting tours in each location.

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Italy Trip Review: Rome, Florence, Tuscany, Amalfi Coast, Pope Francis’ Funeral, Wine, Cuisine, Culture, Museums, Relaxation, 10 Nights

Zicasso’s tour operator planned the most amazing trip to Italy for us! My requirements were culture, romance, and relaxation. She delivered on every aspect. Although we missed our tour of the Vatican due to the Pope's funeral, my husband and I actually attended his funeral!! Our hotel, though planned many months before, was next to the basilica where Pope Francis was laid to rest. Talk about being a part of history!

We stayed in a beautiful converted villa to boutique hotel in Florence; got whisked away through the Tuscan countryside in a vintage Fiat 500; took cooking classes; sipped lovely wine, accompanied by excellent lunches on our winery tours; soaked in Italy's rich culture and museum scene; and even ticked the relaxation box by spending time by the pool, in the spa, and resting on our large deck overlooking the Amalfi coastline.

Every tour guide was extremely knowledgeable and personable, and it was evident they loved their jobs. Between memories of the boat ride along the Amalfi Coast, tips from the cooking classes I have already started using at home, and the cases of wine we are eagerly awaiting delivery of, my husband and I will forever hold Italy in our hearts and la dolce vita it provided us. 

Talk with our tour operator; you will be glad you did!

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Italy Luxury Anniversary Tour Review: Sorrento, Tuscany, Cinque Terre, Venice, Gondola Ride, 3 Weeks
"Zicasso’s travel agency carefully and creatively designed our dream vacation to Italy and delivered an outstanding compilation of experiences."

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Italy Trip Review: Rome, Siena, Orvieto, Venice, Pienza, Vatican, Colosseum, Roman Forum, Vespa Tour, E-Bike Tour, 10 Nights

Our trip to Italy was amazing! The tours that were organized for us were all excellent and engaging. 

The Vespa sidecar tour was an incredible way to kickstart the trip and our two teenage boys really enjoyed it. Our walking tours of the Vatican museums and the Colosseum and Roman Forum tours with our guide were excellent. We loved her. She was fantastic. Our tour of the crypts and catacombs was very interesting and the guide was very good.

The hotels were very nice and accommodating, especially in Rome and Venice. The car rental in Rome was good and the car was the perfect size for what we needed. It was just big enough to fit our luggage. 

The hotel in Orvieto was a bit spartan and had plumbing issues. Our tour guide in Orvieto was also great. The hotel in Siena was very nice. Our tour guide in Siena was very nice, but we had some difficulty hearing her. She did explain things nicely and took us to some interesting locations around the city, but not being able to hear her was a little challenging. The e-bike tour in Montepulciano was incredible. The scenic landscapes and the visit to Pienza was a nice surprise. 

Returning the car in Florence was very difficult and our only suggestion is that on the travel documents, the return address be included on the page of the event. We did not think to look back at the rental agreement. Driving in Florence is very difficult and can be overwhelming for some people. 

The train station was organized and it was easy to locate the train. The train ride itself was very easy and fast. 

Venice was outstanding. Our hotel was beautiful and comfortable, and the breakfast was incredible. Due to the difficulty we had in returning the car in Florence, our travel company was kind enough to buy us dinner at an wonderful restaurant in Venice, which was one of the highlights of the trip. 

Our family had a wonderful experience and the trip was so well planned and organized. I will be using our travel company for future trips and, on behalf of my family, I would like to thank you for the time of our lives!

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