Italy

 11 Amazing Days in Italy with Family – Milan to Rome (With Day Trips!)
Italy has long been on our travel bucket list, and in December 2019, we finally made it happen! With two kids in tow, we planned a mix of iconic sights, walkable neighborhoods, kid-friendly attractions, and plenty of gelato breaks. We also asked our parents to join us on this trip and make it an extended family trip. Here’s a day-by-day breakdown of our 10-day family adventure across Milan, Venice, Florence, and Rome—including a magical day trip to Amalfi, Sorrento, and Pompeii.



Cities visited:
Milan (2 Nights) 
Venice (2 Nights)
Florence (3 Nights)
Rome (4 Nights)

Travel Month: December


Itinerary:

📍 Day 1–3: Milan
Stay: AirBnB
Milan is Italy’s fashion capital, but it’s also rich in history and family-friendly charm. We made the most of our short stays before and after our trip.

Attractions visited:
* Milan Cathedral (Duomo)
* Galleria Vittorio Emanuele II (stunning 19th-century glass-domed arcade)
* Piazza del Duomo
* Walk along the Naviglio Grande canals
* San Siro Stadium (for football fans!)

Itinerary Highlights:
Day 1 – We landed in Milan and headed straight to the stunning Galleria Vittorio Emanuele II, one of the world’s oldest shopping galleries. The glass dome and mosaic floor were breathtaking. The kids enjoyed watching the bustling crowd and musicians while we window-shopped. It was the perfect place to get a first taste of Italy and grab an espresso.


Day 2 – We spent our morning exploring the Duomo and Piazza del Duomo. We spent our morning exploring the magnificent Duomo di Milano and the lively Piazza del Duomo, marveling at the intricate Gothic architecture. The kids were fascinated by the grand spires and bustling square filled with music, pigeons, and energy. We were able to go to the top of the Duomo and get fascinating views of the city. After this, we took a family stroll along Naviglio Grande and a visit to Castello Sforzesco.

Day 3 – We kicked off the morning with a visit to San Siro Stadium, home to AC Milan and Inter Milan—an exciting stop for our little football fan! We explored the museum and sat in the team benches. Around noon, we boarded our Frecciarossa train to Venice, enjoying the scenic 2.5-hour journey. We arrived in Venice mid-afternoon and settled into the dreamlike surroundings of this car-free, canal-filled city.


Day 4–5: Venice
Stay: AirBnB
Venice felt like stepping into a storybook. No cars, just boats, bridges, and endless charm.

Attractions visited:
* St. Mark’s Basilica & Campanile Tower
* Ponte di Rialto
* Grand Canal vaporetto ride
* Private gondola ride (we booked this one)
* Murano Glass Factory (optional)

Itinerary Highlights:
Day 4 – We started our Venetian adventure at Doge’s Palace, admiring the ornate ceilings and hidden stories behind its walls. Then we strolled to the Rialto Bridge, where we took in the Grand Canal views and did some souvenir shopping. The kids loved watching gondolas float by. Venice at dusk was truly magical.

Day 5 – Took a small group walking tour of Venice where a local tour guide explained a brief history of Vernice and walked us past some local attractions. Later we explored St. Mark’s Basilica, and climbed the Campanile Tower for panoramic views

Day 6 – After a morning vaporetto ride along the Grand Canal, we caught a late-morning train to Florence.

🏛️ Day 6–7: Florence (with a Pisa and Ferrari twist!)

Stay: AirBnB

Attractions visited:
* Piazza del Duomo & Ponte Vecchio
* Piazzale Michelangelo (sunset spot!)
* Ferrari Museum (Modena)
* Day trip to Pisa (Leaning Tower)


Itinerary Highlights:
Upon arrival, we explored the Piazza del Duomo, walked past the Palazzo Vecchio, and crossed the famous Ponte Vecchio. The city’s Renaissance charm is impossible to ignore—beautiful art, cozy streets, and welcoming cafés made our first day in Florence unforgettable. The kids, in particular, loved the street musicians and the gelato breaks.

Day 7 – We took a detour from traditional sightseeing and made our way to Modena to visit the Ferrari Museum—a bucket-list stop for our son and a surprisingly engaging experience for the whole family! In the evening, we returned to Florence and visited Piazza della Republica. We ended the day at Piazza le Michelangelo, where we watched the sunset over Florence’s skyline. It was one of those picture-perfect family travel moments.

Day 8 – We took a morning train to Pisa and made our way to the famous Leaning Tower, where we snapped fun photos and admired the surrounding square. After a quick lunch, we returned to Florence, collected our luggage, and headed to Rome in the late afternoon. We arrived by early evening and checked into our hotel, excited for Christmas in the Eternal City.

️Day 9–11: Rome & the Vatican (with a Day Trip to Amalfi)

Stay: AirBnB
Rome was the grand finale of our trip—and it did not disappoint! With a mix of ancient ruins, Vatican marvels, and scenic streets, it was the perfect place to end.

Attractions visited:
* Colosseum & Roman Forum
* Vatican Museums & Sistine Chapel
* St. Peter’s Basilica & Square
* Trevi Fountain & Spanish Steps
* Quirinale Palace & Pantheon
* Day trip to Amalfi Coast, Sorrento, Pompeii


Itinerary Highlights
Day 9 – We set off early for a guided day trip that included stops in Pompeii, Amalfi, and Sorrento—a long day, but worth every second. Walking through the ruins of Pompeii brought history to life for all of us. The dramatic cliffs of Amalfi and the charming streets of Sorrento gave us a taste of southern Italy’s magic. The kids enjoyed the drive along the coastline, and we were all in awe of the views.

Day 10 – We started with a guided visit to the Colosseum and Palatine Hill, diving deep into ancient Roman life. Later, we visited the Sistine Chapel and Vatican Museums, marveling at Michelangelo’s frescoes. We stopped by the Pantheon and ended the day at the Altar of the Fatherland, where the panoramic terrace offered sweeping city views.

Day 11 – On our last full day in Rome, we visited Castel Sant’Angelo, wandered around Quirinale Palace, and made our final wish at the Trevi Fountain. It was bittersweet knowing our Italian adventure was coming to an end, but we made sure to soak in every moment.

 Quick Travel Tips
* Trains: We used Frecciarossa high-speed trains between cities—super efficient and comfortable. Definitely book in advance.
* Tickets: Most of our attraction tickets were booked online ahead of time to save time and skip lines.
* Day trips: The Amalfi/Sorrento/Pompeii trip was arranged through an agent. If you’re interested, I’m happy to share her contact info—she was excellent!
* Weather: December in Italy is cool (and sometimes rainy), so pack layers, especially for the kids.
* Ferrari: The Ferrari Museum is far from Florence—but if you have car lovers in the family, it’s totally worth it!

💬 Final Thoughts
Italy with kids was a dream! From Venetian canals to Roman ruins, there was something for each of us. We kept things flexible but well-planned—and having pre-booked trains and attractions made everything run smoother.
If you’re planning your Italy family vacation, feel free to comment below or DM me for tips. ✨