Two Week Italy Itinerary flying in and out of Milan

Our two week Italy trip was our first kid-free vacation and we wanted to make the most of it without feeling like it was too rushed. We discussed our must-see places and with flights in and out of Milan, we planned a two-week itinerary for Italy. It wasn’t easy, there are so many wonderful Italian cities and towns. 

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Day 0: Flying to Milan

Our flight with Thai Airways left Melbourne at 4:15pm and we had a connecting flight from Bangkok to Milan.

Day 1: Arriving in Milan 

Our flight landed in Milan at 7:35am but we couldn’t check in to our Airbnb until the afternoon.
Read our one day in Milan itinerary. 

Day 2: Train from Milan to Venice

We knew we wanted to include Venice in our two-week Italy itinerary. To get there, we arrived at Milano Centrale ready to catch our pre-booked Italo train to Venice at 8:30am. After a two-hour train ride, we walked from Santa Lucia Station to Hotel Filu to leave our bags and explore Venice. Read my post on our one day in Venice.

Day 3: Train from Venice to Rome

Wanting to make the most of our time in Venice, we got up and out early and found the streets were very quiet. Returning to the hotel to check out, we were able to leave our bags and see more of Venice. We got a short Vaporetto ride over to the island San Giorgio Maggiore for a view of Venice from above. 

We collected our bags and got on our 4pm train to Rome. The train was delayed and we sat on it wondering why we weren’t leaving before it was announced. After a twenty-minute wait, we were on the way. Arriving at Termini station just after 8pm we then had to get the subway and find our AirBnB in the dark.

Day 4: Rome   

Our AirBnB was in a great location for sightseeing in Rome. We walked to Palatine Hill to start our day.
Read our two day Rome itinerary.

Day 5: Rome  

For our second full day in Rome, we took the subway and started at Trevi Fountain before walking to lots of other sights. 

Day 6: Getting to Cinque Terre from Rome  

After checking out of our AirBnB at 10am we got the subway to Termini Station. We had a bit of a wait as our Trenitalia train was booked for 11:57am. We bought a takeaway panini before boarding the train. Our tickets were booked to La Spezia and we had to purchase tickets onwards to Corniglia. We also purchased Cinque Terre cards to use the next day.

From Corniglia station we walked over 300 stairs up to the town, I regretted doing it with our backpacks on. After meeting our AirBnB host at her cafe, she showed us to our room. We wandered around and bought a bottle of local wine to enjoy while watching the sunset from our room window. We had an amazing meal at a local restaurant.
Read about our stay in Corniglia.

Day 7: Walking in Cinque Terre  

Starting our day with a fantastic breakfast at our hosts’ cafe we then began hiking to Vernazza and Monterosso. It was an absolutely beautiful walk along the coast with stunning views.
Read our full post about travel to Cinque Terre. 

Day 8: Travel from Cinque Terre to Florence via Pisa

We again had a lovely breakfast before checking out of our Airbnb. We took the shuttle down to Corniglia Station, went to La Spezia and then bought tickets to Pisa. Once at Pisa Central Station, we walked about 2km to see The Leaning Tower of Pisa. We crossed the Arno River and I thought the area was quite pretty. It started to rain and then we got lost and by the time we reached the tower, I wasn’t impressed. 

The Leaning Tower of Pisa is much shorter than I had expected. After walking in the rain with a heavy backpack and then having to walk back to the station, I didn’t think it was worth the effort. I did find the cathedral and baptistery were interesting with intricate details. I’m glad we didn’t deliberately work Pisa into our itinerary but as we had to connect at the station to get to Florence, It was a pretty easy detour, even if I did whine about it.

Our Florence AirBnB was within walking distance from Firenze SMN Station and self-check-in was nice and easy. We bought a takeaway pizza back to the apartment.

Day 9: Walking around Florence  

For our day in Florence, we walked around the city, viewing some amazing architecture.
Read: what to do in Florence besides museums.

Day 10: Siena day trip from Florence

With another full day in Florence, we decided to go on a day trip to Siena. From the bus station in Florence, we bought return tickets on the rapid bus to Siena. We walked to attractions including Duomo di Siena and Piazza Del Campo. It was very crowded and at times difficult to enjoy walking the streets.

Day 11: Getting to Lake Como from Florence  

We had a Trenitalia booking for 12pm to Como via Milan. Arriving at Como San Giovanni Station at 2:45pm we walked 1km to our hotel Albergo Terminus. It was right on the lake and we had a little view from our room. After walking to the funicular we found a note on the door stating it was closed for maintenance. We chose to have drinks at a place opposite the lake, then strolled around and had Gelato. Later we had dinner at Riva cafe.

Day 12: Boat from Como to Bellagio  

In the morning we walked around Como, finding some wonderful architecture. We came across a little handmade Christmas market and bought some presents. Before 12pm we headed to the ferry area, bought our tickets and waited for the slow boat to Bellagio. We grabbed some seats on the side and enjoyed the journey up Lake Como, passing by the little towns before getting off in Bellagio. 

We were picked up in the hotel shuttle to go uphill to check in at Borgo Le Terrazze. Our room had a balcony with beautiful lake views. We went back into town and had dinner at La Fontana. Lake Como post coming soon.

Day 13: a day in Bellagio 

Our day started with taking the shuttle bus down to wander around the town while it was quiet. We got an apple pastry for breakfast before strolling around the pretty streets. A walk along the road took us to Punta Spartivento, a viewpoint on the tip of Bellagio’s peninsula. 

Originally I had thought we would take a boat and explore other towns but we found ourselves wandering around Bellagio, having a late lunch, relaxing with a bottle of wine on our balcony and enjoying another dinner in town and bringing back tiramisu.

Day 14: Travel from Bellagio to Milan via Varenna

In the morning we took a short boat ride from Bellagio to Varenna. After disembarking we strolled around this picturesque town. It was quite a workout with stairs leading up to streets and down to the water. I found a little shop selling handmade products and bought myself a little bracelet and a present for my mother-in-law for looking after our kids. We made our way to the train station and bought tickets to Milan.

In Milan, we went up to the incredible Duomo rooftop terraces and ate our last pizza and gelato in Italy.

Day 15: Fly out Milan 2:05pm 

We booked our flights in and out of Milan because it was the cheapest option. Unfortunately, maybe the sacrifice for the cost is time and frustration. After a long process on our way in, it was the same on the way out.

Two-week Italy itinerary 

One thing I have learned (still learning) with planning trip itineraries is to not overdo it. There are still lots of places in Italy we would like to visit but I think it’s best to leave things for future travels rather than cram heaps in at once. We felt we experienced each place well on our two-week Italy itinerary. The only thing we would have changed was to have more time in Cinque Terre for another hike. See our full cost breakdown for this trip.

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