Italy was one of our must-see destinations, and it did not disappoint. From incredible food and famous landmarks to learning how to row gondolas and climbing volcanoes, history and adventure seemed to surround us at every turn.
This 16-day Italy itinerary takes you through iconic cities like Venice, Florence, and Rome, along with scenic Tuscan countryside road trips and the unforgettable experience of walking through the ancient ruins of Pompeii.
Here’s how our time in Italy unfolded.
Days 1–4: Venice – Canals and Colourful Islands
Built across more than 100 small islands connected by bridges and canals, Venice quickly became one of our favourite places to wander.
Over four days, we explored maze-like alleyways, crossed countless bridges, explored Piazza San Marco and Doge’s Palace, and admired the city from the water aboard Vaporetto ferries and gondolas. One of our favourite experiences was taking a gondola rowing lesson, which gave us a whole new appreciation for the skill required to navigate Venice’s narrow canals.
We also spent a day exploring the nearby islands of Murano and Burano. Watching glassblowers at work in Murano fascinated the kids, while Burano’s colourful homes and peaceful canals made it one of the most photogenic places we visited in Italy.
Days 5–7: Florence, Pisa, and San Gimignano Road Trip
Next, take the train from Venice to Florence before spending a few days exploring both the city and the surrounding Tuscan countryside.
Florence offered the perfect mix of history, art, and relaxed Italian charm. We spent our days wandering lively piazzas, visiting the Duomo, petting the Fontana del Porcellino, and standing in awe beneath Michelangelo’s Statue of David at the Accademia Gallery.
Using Florence as a base, we also rented a car for a road trip through Tuscany, visiting the Leaning Tower of Pisa and wandering the medieval streets of San Gimignano. Between the gelato shops, scenic drives, and open piazzas, Tuscany ended up being one of the most relaxing parts of our Italy itinerary.
For full details, see our 3-Day Florence, Pisa, and San Gimignano Road Trip.
Day 8: Travel to Rome
After a few busy days, we slowed things down. We arrived in Rome and spent the afternoon settling in and exploring the neighbourhood around our hotel.
Days 9–12: Rome – Ancient Ruins and Gladiators
Rome was one of the busiest but most fascinating stops on our itinerary. Around nearly every corner, we found lively piazzas, beautiful fountains and sculptures, and ancient ruins packed with history.
Highlights included imagining gladiators battling at the Colosseum, standing in awe of the Sistine Chapel and Saint Peter’s Basilica in Vatican City, and visiting the hands-on exhibits at the Leonardo da Vinci Museum. But most of all, we loved roaming around Rome—tossing coins into the Trevi Fountain, seeing the Pantheon, and simply grabbing gelato and watching famous landmarks light up after dark.
Day 13: Travel to Naples and Positano
From Rome, we rented a car and drove south to Naples, which served as our base for visiting Pompeii and Mount Vesuvius. Following several busy sightseeing days in Rome, this slower travel day gave us time to relax before diving into one of the most fascinating historical experiences of our trip.
Once settled into our Airbnb, we continued another hour along the coast to Positano, where we spent the afternoon admiring the colourful cliffside homes, narrow streets, and beautiful coastal views.
Days 14–15: Pompeii and Mount Vesuvius
Walking through Pompeii felt like stepping directly into the ancient world. The remarkably well-preserved streets, homes, shops, and amphitheatres gave us a glimpse of life nearly 2,000 years ago, before Mount Vesuvius erupted in 79 AD.
The boys were fascinated by the stories of the eruption, the preserved ruins, and the plaster casts uncovered during excavations. The following day, we climbed Mount Vesuvius itself, standing on the rim of the volcano while overlooking Pompeii and the Bay of Naples below.
For full details, see Pompeii and Mount Vesuvius: A City Frozen in Time.
Day 16: Return to Rome
Return to Rome and enjoy one last gelato before heading home!
Travel Tip: If you have an early flight, consider returning to Rome in the afternoon after hiking Mount Vesuvius to make your travel day a little less rushed.
Italy Left Us Wanting More
Our time in Italy gave us a deep appreciation for the country’s beauty, history, and culture. Between ancient ruins, vibrant canals and islands, Renaissance art, volcanic landscapes, and endless pasta and gelato, Italy offered an incredible mix of experiences that kept both kids and adults engaged throughout the trip.
We left feeling like we had only scratched the surface and were already dreaming about returning one day.
Ready to Explore Italy?
Check out these related posts to help plan your trip:
• 4-Day Venice Itinerary with Kids
• Fun Things to Do in Venice with Kids
• Becoming Gondoliers: Learning to Row a Gondola in Venice
• Murano and Burano Day Trip from Venice
• Exploring Murano Island, Venice
• Exploring Burano Island, Venice
• 4-Day Itinerary in Rome with Kids
• Inside the Colosseum: Touring Ancient Rome with Kids
• The Vatican with Kids: What to Expect & How to Plan
• Roaming Around Rome: A Walking Tour for Families
• Pompeii and Mount Vesuvius: A City Frozen in Time
• 3-Day Florence, Pisa, and San Gimignano Road Trip
