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

Multi-Generational Italy Vacations & Tours

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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.

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Tailor Made Itineraries

Get inspired with our sample trips below. Let our travel specialists customize a trip just for you.

Young girl wearing carnival mask in Venice, Italy
Wonders of Italy Family-Friendly Tour: Rome, Florence, Venice and More

10 Day Custom Tour

Dynamic pricing from $3,575

Effortless charm, captivating cuisine, and immersive artistry exemplify your 10-day family Italy vacation. Travel from Rome to Venice on this 10-day family vacation to discover the fun of ancient life, Renaissance beauty, traditional pasta, hand-crafted masks, and the techniques of gladiators. Whether wandering through the Vatican Museum's empty galleries or witnessing the Uffizi Gallery's embracing beauty, Italy’s boundless splendor will exceed your family’s greatest expectations.

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Piazza Venezia in Rome, Italy

Bring your family to remarkable cities and explore rich history that prevails from the shimmering canals of Venice to the rolling hills of Tuscany and the ancient districts of Rome on this 9-day family Italy trip. Led by guides with insider knowledge of significant stories, enlightening culture, and sumptuous cuisine, this customizable family vacation captures the best of Venice, Chianti, and Rome, while introducing you to each destination’s hidden secrets.

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The ruins of Pompeii in Italy.
Family Trip to Italy: Nature, Ancient Temples, and Cuisine

12 Day Custom Tour

Dynamic pricing from $4,291

Bask in the splendor of La Dolce Vita from the Amalfi Coast to ancient Sicilian temples during your 12-day family Italy tour. Stroll cobbled lanes where ancient Rome presses against medieval walls. Wander the lush volcanic base of Mount Etna where grapevines thrive. Uncover ancient Greek theaters and recently excavated Roman mosaics. Your family-friendly tour reveals artistic splendor and as you celebrate the simple pleasures for which Italy is known.

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Mom and daughter admire the view of Florence from Piazzale Michelangelo
One Week Family Vacation to Tuscany and Cinque Terre

7 Day Custom Tour

Dynamic pricing from $2,501

The rolling hills of Tuscany and unrivaled landscapes of Cinque Terre provide the perfect backdrop for this memorable 7-day family vacation. Enjoy exclusive experiences and private tours, such as a pizza-making course, a family bike ride, and a gelato tasting, while you bask in the Tuscan sun and create lifelong memories. Immerse yourself in the beauty, history, and delicious cuisine of Tuscany and Cinque Terre during this unforgettable family vacation.

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Ponte Vecchio bridge at sunrise, Italy, Florence
Amazing Family Italian Vacation in 7 Days: Rome, Venice, and Florence

7 Day Custom Tour

Dynamic pricing from $2,501

See the greatest cities of Italy through the eyes of a child and learn how to make the country’s culinary specialties. Enjoy a gondola ride in Venice, a guided tour of Rome, and a freshly prepared Tuscan meal. Take in the sights of the unsurpassed Italian countryside from the luxurious comfort of a first-class train carriage and witness the incredible art that fills the Vatican Museum with this Italy tour package. If you’ve ever wanted to show your kids the wonders of the world, this is the place to start.

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Umbrian Hills in the Midday Sun, Italy
Italy Family Vacation for First Timers

9 Day Custom Tour

Dynamic pricing from $3,217

Immerse yourself in Italy with unique and interactive experiences at every turn. Travel through Italy’s heartland with stops in bustling, metropolitan cities and countryside estates before walking the cobblestone avenues of ancient gladiators, sailing down gentle waterways, and basking in the Tuscan sunshine. The architectural and artistic masterpieces, colorful frescoes, and gorgeous mosaics will give you something to take your breath away before you master the art of Italian cuisine and learn the techniques behind the perfect pizza, creamy gelato, and chocolate delights. Cathedrals, castles, museums, and monuments are waiting to be explored, and expert guidance in addition to customized experiences at each location make this luxurious, 9-day adventure through Italy the perfect family break.

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Positano, Italy
Italy Family Vacation: Coastline, History, and Food

10 Day Custom Tour

Dynamic pricing from $3,575

Experience history and culture as it comes to life during your custom-tailored family tour through Italy that highlights the monuments, landmarks, and customs from the Amalfi Coast to Bologna, Rome, and Florence. Your immersive experience captures the splendor of Renaissance art and the brawn of ancient gladiators, offering a unique perspective of the past. Make delicious pizza as a family, scour for treasures in celebrated museums, and participate as classic cities become interactive galleries that display ancient ruins and magnificent architecture. Whether sampling delicious cheese or wandering through a hidden corridor, your family-friendly tour through Italy will reveal tradition and unforgettable adventure.

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Gondola ride near the Rialto Bridge on the Grand Canal in Venice, Italy
Cultural Exploration Family Tour of Northern Italy

10 Day Custom Tour

Dynamic pricing from $3,575

From the canal waters of Venice to the jagged and daring peaks of the Dolomites, Northern Italy’s diverse landscape brims with adventure and ancient history. Embark on a gondola ride down Venice’s famed Grand Canal, shop on the 16th-century Rialto Bridge, hike the rugged Dolomite Mountains, and discover the allure of bustling Milan. You will relax on the picturesque Lake Como, making memories with your children as you splash in its refreshing waters. Visit 500-year-old villas, explore an elaborate garden maze and discover ancient Roman secrets in Verona on this customized, 10-day tour of Northern Italy.

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Ultimate Two-Week Family Vacation to Southern Italy

14 Day Custom Tour

Dynamic pricing from $5,007

From scaling the heights of a dormant volcano to exploring the depths of a royal escape route, this luxurious, 14-day tour of Southern Italy provides destinations and activities that will be treasured by your whole family. Across three major regions, this journey focuses on providing a balanced approach to travel with curated tours and activities that have been combined with plenty of time to relax on a beach with a good book. No matter what your family’s travel style is, the city of Naples, the Sorrentine Peninsula, and the exotic city of Palermo will bring you closer together and provide memories to last a lifetime.

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Sforza Castle Castello Sforzesco is one of the symbols of Milan, Italy
Family Friendly Lake Como Vacation

8 Day Custom Tour

Dynamic pricing from $2,859

This luxurious 8-day journey will begin with one night in the fascinating city of Milan before setting your sights on the gorgeous Lake Como. From Como to Lenno to Bellagio, experience some of the very best towns and villages along Lake Como. Indulge in a pasta-making class and partake in a tour of filming location while exclusive family classes and private tours immerse you in the culture of the area

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Tram with Arco della Pace in the background, Milan, Italy
One Week Milan Family Vacation

7 Day Custom Tour

Dynamic pricing from $2,501

Milan is a city that is on the cutting edge of the modern fashion and business world, yet is rich in history and culture. Experience it all during an exciting and immersive 7-day, family vacation to this magnificent city. Enjoy unparalleled views of Milan from the roof of its cathedral, visit ancient Sforza Castle to explore its multiple museums, and get a chance to view Leonardo da Vinci’s masterpiece painting of the Last Supper. A day trip to stunning Lake Como and a private food tour of Milan culminate this once-in-a-lifetime trip. See the best of Milan you’re your family during this magnificent vacation that will have your thinking about returning to Italy for the rest of your lives.

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Bologna, Italy
Luxury Italy Family Vacation

16 Day Custom Tour

Dynamic pricing from $12,475

From the pleasures of high culture to the joys of adventure, this 16-day luxury Italy family vacation offers something for all ages. Taste buds will revel in the joys of Bologna, eyes will feast upon the immaculate detail of the Sistine Chapel, and the beauty of the Mediterranean sunlight will shine brightly.  No matter your preference, there is something in Italy for everyone in the family.

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More About Multi-Generational Italy Vacations

Italy Travel Guide
Florence, Italy
Italy Travel Guide

From Roman ruins to the Tuscan countryside, there is something for every traveler in Italy.

Our Italy Travel Guide provides helpful tips and inspiration from must-see destinations and top activities to the best time to visit. Discover traditional food and wine, inspirational culture, and amazing cities on a personalized vacation.

For more information on how to make your dream journey a reality, get connected with a top travel specialist by filling out a Trip Request.

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Top 10 Things to Do in Italy with Family
Mother and daughter on gondola ride in Venice, Italy
Top 10 Things to Do in Italy with Family

Combine the following essential experiences on a family vacation to Italy. They share Mediterranean culture, highlight Roman heritage, and introduce you to natural beauty.

Several iconic seas circle the Italian peninsula, comprising views from charming coastal towns pinned to lush headlands. Across the countryside, cities and fortresses punctuate the rolling landscape, opening their doors to families who wish to unpack the origins of Ancient Roman civilization. All ages can absorb the marvelous atmosphere and signature experiences during family vacations in the Mediterranean.

You and yours will spend time at iconic destinations and on illustrious islands as you relish the following essential experiences in Italy.

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How to Plan a Trip to Italy: Frequently Asked Questions
Skyline highlighting the architecture of Rome, Italy
How to Plan a Trip to Italy: Frequently Asked Questions

As you plan your trip to Italy, consider our tips with the following answers to the most frequently asked questions.

From dreaming of the sunflower fields in Tuscany to searching the ruins of Rome for ancient treasures, you can book a vacation in Italy using our ideas as inspiration. Enjoy the pleasures of La Dolce Vita or alpine panoramas, lounging on golden beaches, or embracing rolling vineyards. It is all about finding the information you need to plan the right trip for you.

Whether you are designing a first-time Italian vacation as a couple or returning to the Mediterranean jewel with family, we share how to plan a stress-free trip.

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Best Time to Visit Italy
Summer Tuscany scenery with red poppy flowers and grain fields surrounding cute Vitaleta chapel and Pienza on the hill in Italy
Best Time to Visit Italy

The best time to visit Italy is in the spring and early summer months, from March through June. During this time, the weather is great for the beaches, sightseeing, wine tasting, food tours, and more. Fall, particularly September and October, are also lovely times, when Italy is quieter and the fall colors are on show.

Your ideal experiences also affect the best time of the year to visit Italy for your vacation. Skiing in the Dolomites is exceptional in December, while enjoying the sun-washed beaches of Sicily is best in May. Rome is brilliant in April, while Florence is stunning in September.

From wine tasting to Roman-ruin exploration and coastal sightseeing, find the best time for your experience. As a family, couple, senior, or adventure traveler, we share ideas to help ...

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Reviews of Zicasso's Referral Service

4.89 stars based on 4398 reviews.

Italy Travel Review: Tuscany, Cinque Terre, Lake Como, Private...
"Giulio at this travel company did an exceptional job arranging...

Reviewed By Irene P.

Italy Trip Review: Venice, Como, Tuscany, Florence, Rome,...
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Italy Trip Review: Milan, Verona, Venice, Lake Como, Lake...
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Italy Vacation Review: Shopping in Milan, Pompeii Excavations,...
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Vacation Review: Luxury Italy Tour, Lake Como, Menaggio,...
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Luxury Italy Trip Review: Rome, Porto Ercole, Florence,...
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