Kid-Friendly Family Tour of Italy's Highlights

A 10 day trip to Italy 
4.75 out of 5 stars
16 reviews

Become gladiators, search for priceless paintings, and indulge in unforgettable adventures with a custom tailored family-friendly Italy itinerary. Relish a chance to blend fun and education with culture that the kids can touch. Knead handmade pasta dough under the guidance of a private chef and then wander through hidden corridors and along the labyrinthine Hypogeum in the Colosseum. Explore extinct volcanic craters and learn the art of making fresh gelato in a medieval town. Your private family Italy tour itinerary will offer flavorful delights, ancient marvels, and secret catacombs to create memories that will last a lifetime. 

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General Information

Detailed Itinerary

Places Visited 

Rome, Florence, Pisa, Orvieto, Lucca, Siena, Taormina, Mount Etna, Modica, Syracuse, Catania

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

Day 1: Rome – A Family Occasion in Rome

Rome conjures images of ancient architecture and powerful gladiators, noble senators and Baroque palaces. The aroma of fresh pasta drifts out of local trattorias,  traditional Italian restaurants. The sunlight washes over the golden sandstone along the façade of Castello Sant’Angelo. Gelateria showcase the vibrant colors of creamy mounds of gelato waiting to be scooped. Your flight lands at Rome Fiumicino Airport, where your private transfer greets the family upon arrival. Upon entering the city, you find elegant fountains trickling with water and the opulent columns and brass statues of the 19th-century Victor Emmanuel II Monument. The pillars along the upper colonnade reach 50 feet tall and resemble the wings of a classical temple.

From the window of your hotel located along a street lined with shading oak trees, you take some time to embrace the beauty of the Eternal City. Your guide greets you in the lobby, eager to introduce the family to the grandeur of Rome during a walking tour of the historic city center. The Trevi Fountain remains an icon of Rome and features the dramatic posture of Oceanus, Titan of the Sea. The mouth of an ancient aqueduct continues to feed the fountain as water falls over the smoothed rocks into the crystal clear turquoise pool. The kids take coins and follow the other visitors by turning their backs to the water and throwing the coins over their shoulders and into the pool. They hear the metal plop; according to legend, it means they will return to Rome again.

What’s Included: airport transfer, accommodation, tour

Day 2: Rome – A Day in the Roman Life

At breakfast, the scent of espresso accompanies the aroma of fresh brioche filling the dining room of the hotel. The kids delight in the sweet flavor and flaky crust of the pastries before you meet your guide and set out to Gladiator School. The kids embark on an active lesson connected to the Museum of Gruppo Storico Romano. Gladiatorial artifacts fill the gallery, from swords to shields, to helmets and sandals. The kids try on replicas of armor used in the battles at the Colosseum. Their guide fits you with traditional training garments and wooden swords. You enter the training grounds and learn the movements necessary for victory in the arena. The scent of oleanders drifts over the unpaved arena.

The kids twirl their wooden swords while learning to parry. They jump over twirling posts and under rotating bars. They run through swinging bags to test their agility. At the end of the training, they become certified gladiators before exploring the grounds of the ancient city beginning with the Colosseum. The outer walls are more than 150 feet tall and are nearly 1,800 feet long. The family, newly certified in the gladiatorial arts, eagerly enters the interior to find a grand stadium holding up to 50,000 spectators in its heyday. The wooden stage has long faded and given way to a view of the two-story tall walls creating a labyrinth at the heart of the arena. It is here that gladiators and exotic animals once waited for the battles to begin.

What’s Included: accommodation, tour, breakfast

Day 3: Rome – Hunting the Treasures of Rome

In the morning, the sunlight washes over the verdant trees and blossoming flowers of the Borghese Gardens. Locals jog along the walkways as couples take to the lake to paddle in front of a 19th-century replica of a Roman temple. After breakfast, your guide greets you at the hotel and leads you to the framing pillars around St. Peter’s Square. The dome of the basilica reaches a height of nearly 450 feet and shimmers with a golden crown. An Egyptian obelisk decorates the center of the oval shaped piazza. Your guide has created an elaborate scavenger hunt for the entire family to enjoy while wandering through the marvelous galleries of the Vatican Museums.

The museum began in the early 16th century under the reign of Pope Julius II and has since grown its galleries to encompass 460,000 square feet. The kids will be in awe upon learning that Vatican City is an independent state of just under 110 acres. In the central courtyard, you will discover a gigantic bronze pine cone statue that once resided in the Pantheon. Peacocks frame the pinecone, perched atop two stone pillars. Inside the halls, you will venture to the Gallery of Maps while stepping beneath the 16th-century topographical maps of Italy adorning the walls and ceiling. The family can search these maps for the different areas of the country to pinpoint geographical locations according to their place in history.

What’s Included: accommodation, tour, breakfast

Day 4: Florence – A Different View of Historical Cities 

At breakfast, the kids share their favorite part of the scavenger hunt through the Vatican Museum. They talk about the demons they saw on the walls while exploring the Sistine Chapel. They recount who among them was the first to find the hidden figure of Rafael in the master painter’s work School of Athens. The sunlight drifts over the city and filters through the windows in the Church of Sant’Ignazio di Loyola. The trompe l’oeil fresco draped across the dome inserts the viewer into the swirling movement of angels and in the heavens as painted by the 17th-century Baroque master Andrea Pozzo.

After the meal, your private transfer greets the family in the hotel lobby and escorts you north towards Florence. After discovering the thrills of Orvieto, you arrive in the Tuscan city of Siena. The preserved ramparts and historic center highlight the city that once rivaled Florence for supremacy in power and art. Your guide leads you on a remarkable walking tour along the winding cobbled lanes and distinctive medieval architecture while offering anecdotes and legends of Siena that the family can connect with. The stories include the vibrant history of the legendary horse race known as the Palio, which takes place twice a year in Piazza del Campo.

Pink stone glints along the façades of Palazzo Sansedoni and Palazzo Pubblico. The sensational 14th-century tower of Torre del Mangia reaches a height of nearly 335 feet. You can climb the steps for an incredible view of the rolling hills of Tuscany and the rooftops of the city below before your tour continues to a small gelateria where the family learns the art of crafting and tasting gelato.

What’s Included: accommodation, transfer, tour, breakfast

Day 5: Florence – Inspired in the Renaissance 

In the morning, crew members take their boats out along the Arno River and row against the rushed current. The shops along the famous Ponte Vecchio, the oldest bridge in Florence, open their doors to showcase glistening jewels and lavish silk ties. After breakfast, your guide escorts the family to the entrance of the Uffizi Gallery. The kids marvel at the living statues decorating the stairway. The figures keep still and silent until they suddenly open their eyes and wink at the family as you pass.

The Uffizi was erected in the late 16th century as the offices of the Florentine magistrates. The sunlight floods the open windows lining the second-story hall and washes over the polished marble floors. The museum galleries contain masterpieces spanning the 13th to 17th centuries, offering insight into the shift from medieval perspective and into how the Renaissance changed the art of Western Europe. Your guide engages the family in conversation about the pieces, turning the art into an interactive experience that goes beyond just viewing.

The kids find the works thrilling and unique; you find the work breathtaking, especially when facing Botticelli’s renowned piece The Birth of Venus. The 15th-century work recounts the birth of the Roman goddess and her ride upon her giant seashell to the shores of Cythera. Zephyrus, the god of the west wind, can be seen gently guiding her on her way. You can step beyond the artwork visible to the public and thrill the kids by taking them through the secret passageway known as the Vasari Corridor which connects the Uffizi to the Pitti Palace across the river.

What's Included: accommodation, tour, breakfast

Day 6: Florence – Fun in Pisa and Lucca

In the morning, the scent of fresh brioche drifts out of the secret bakeries around the historic city center. The sunlight glints off the white, pink, and green marble façade of the elegant cathedral. The red brick dome crowns the cathedral and dominates the city skyline. You meet your private driver after breakfast and make your way through the Tuscan countryside to reach the fabled city of Pisa. You venture to the Piazza dei Miracoli, home to the legendary Leaning Tower. The structure immediately captures the imagination of the kids. You have wanted to see the way the tower lists for years.

The tower reaches a full height of more than 180 feet, and the kids will wonder at how the edifice can lean nearly four degrees without falling over. The tower was erected between the 12th and 14th centuries, with subsequent naval victories calling for another celebratory layer. The Gothic and Romanesque elements are distinctly Pisan. You climb to the top of the tower, up nearly 300 steps to reach the top. You can feel the magnificent list and notice the way the surrounding city and countryside have tilted. The wonders of the day continue with your time in Lucca, a city known for its vibrant medieval walls. Napoleon Bonaparte’s sister converted the historic walls into public parks. Locals ride their bikes along the paved lanes and enjoy the aroma of the trees and flowers that blossom along the outskirts of the historic city center. 

What’s Included: accommodation, tour, breakfast

Day 7: Taormina – At the Edge of the Ionian Sea

At breakfast, the kids share their favorite moments in Florence. They recall their time watching the cobblers craft shoes or the scent of the leather bookbinder’s store on the narrow streets of the Otrarno neighborhood. After the meal, your private transfer escorts the family to Florence Peretola Airport for your flight to Catania, Sicily. You continue to the cliff-side town of Taormina, which overlooks the azure waters of the Ionian Sea. The rocky terrace offers spectacular views down to the lapping water and up to the snowcapped peak of Mount Etna, Italy’s most active volcano. The remains of a castle crown the upper promontory and boulders frame a small islet connected by a narrow sandbar to the beach.

After taking a moment to enjoy the comforts of your luxurious hotel, your guide leads the family on a walking tour of Taormina for an immersive exploration of the historic streets. Carnations and hydrangeas grow in flowerpots lining the second-story windows. The scent of candied orange peels and buttery cookies emanates from Pasticceria Chemi. Cafes place tables and chairs along the cobblestones of Piazza IX Aprile for views across the bay leading to the volcanic summit. The Greek Theater dates back to the third century BC. The architect used the natural grade of the hill to account for the stadium seating, which reaches a diameter of nearly 390 feet. The ancient, red tinted stone frames the turquoise water in the background and guides your eyes to the ever-present summit of Mount Etna.

What’s Included: accommodation, transfer, tour, breakfast

Day 8: Taormina – Fun and Family on the Coast

The gentle tide breaks against the pebbles and boulders on Isola Bella. The ivory sandbar connects the shores of the small islet to the sun-drenched shores beneath the cliffs of Taormina. Sunlight pierces through the Norman Gothic windows of the 13th-century palace of the Duke of Santo Stefano, revealing the Arab accents. Your private chef greets the family after breakfast, eager to lead you through the open market of town to view the brightness of the produce and the freshness of the seafood.

Buckets of mussels and ruby prawns line the aisles separate from the glowing tomatoes and the shimmering purple skin of washed eggplants. Your chef picks the ingredients necessary for producing a traditional Sicilian meal. In the comforts of a private kitchen, your chef instructs the family on how to make the delectable handmade pasta. The kids help by making a mound of flour, poking a hole in the middle, and cracking eggs into the cradle. You stir the egg until it combines with the flour to make dough.

The kids have fun using their hands to kneed the soft, sticky dough into a ball. As the dough rests you begin making traditional meatballs and sauce to accompany the hardy pasta.  After the class, the day is yours to enjoy the luxuries of Taormina at your leisure. You can make your way to Mazzeo Beach to lounge beneath the shading umbrellas and dip your toes into the refreshing water of the Ionian Sea.

What’s Included: accommodation, tour, breakfast, lunch

Day 9: Taormina – Adventures in Sicily

A short climb along the ascending hills above Taormina leads to the summit of Monte Tauro, which stands at 1,240 feet above sea level. The panoramic view from the pathway of Via Circonvallazione overlooks the rooftops of Taormina, the Greek Theater, and the glistening waters of the coastline. After breakfast, the day is yours to indulge in the endless offerings of adventures around the island of Sicily. You could make your way to the mountaintop town of Modica to embrace a chocolate tour or trace the ancient history predating the Roman Empire in Syracuse.

For a unique and exciting day, you travel to the base of Mount Etna for a four-wheel drive expedition. The volcano peaks at nearly 11,000 feet above sea level. You board your vehicle and begin the climb the rugged landscape. The trees rustle in the gentle breeze and gives way to sporadic underbrush. Your guide refers to Etna as “The Mountain,” as most locals do. He explains the geological and cultural history shaped by the eruptions in the area.

The jeep rocks back and forth over the larger rocks leading to the lunar landscape of the high-altitude peaks. The jeep stops near the walking path leading to Crateri Silvestri, located at almost 6,000 feet above sea level. The collection of craters opened during an eruption in the late 19th century and highlighted the immense power of volcanic activity in the indented landscape. Your guide explains that the craters are no longer active and completely safe to walk in and around.

What’s Included: accommodation, tour breakfast

Day 10: Taormina – Bringing the Family Together

The best family vacations bring everyone together to create lasting memories. At breakfast, the kids once again retell their favorite moments during your time in Sicily. They excitedly reminisce about their time on the mountain watching the steam drift from the distant fumaroles and about learning how to make perfect Sicilian pasta by hand. You sip a refreshing espresso and enjoy the view to the water. The cafes set out their tables in Piazza Vittorio Emanuele. The shops along Corso Umberto place elegant ceramics in their window displays to showcase the topaz, crimson, and saffron colors of their wares. Your private transfer greets you in the hotel lobby after the meal and escorts you to Catania-Fontanarossa Airport for your flight home.

What’s Included: airport transfer, breakfast


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.