Located in Central Italy. It it is known for the beautiful landscape and for the many picturesque towns. We decided to hop on a train to make our way to Cortona from Rome. Taking the train in Italy it is easy and affordable. Absolutely recommend it if you are visiting different cities.

We arrived to the train station in Cortona and our Airbnb host was waiting for us. He drove us to our place where we would be staying for the next 5 days. He walked us through and showed us around. Collin and I just kept looking at each other. This one bedroom house was BEAUTIFUL, it had a breathtaking view and it was about a 5 minute walk to Cortona. From every window in the house you could look out at the rolling hills and vineyards.

It was everything and even more than we had expected. He even welcomed us with a bottle of red wine. To this day it has been our favourite Airbnb that we have ever stayed at. 

This is the link to our AirBnB https://www.airbnb.com/rooms/13839869

Day 1: Getting settled

We arrived in Cortona around 2pm. We decided to get organized and pick up some groceries for the next few days. As we walked we came across this cute grocery store. Picked up the essentials (which included different cheeses and meats oh…and wine of course).

We made our way back to our Airbnb and got settled. We cooked some pasta with spices we picked up in Rome and enjoyed a glass or two of wine. Collin is a great chef so the pasta turned out delicious!

Day 2: Getting to know Cortona

Exploring Cortona was the plan for day 2. We made our way to Piazza della Repubblica to enjoy a cappucino. Every morning had to start with a cappuccino and a little pastry.

Cappuccino at Piazza Della Repubblica

Getting lost through the hallways in Cortona was a must. We found out that the fountain from the movie “Under the Tuscan Sun” is actually not there. It was placed there for the movie, which was disappointing. We had watched the movie before arriving.

It was lunch time so we decided to find a restaurant with a nice view and yummy food. We came across Ristorante Tonino. Walked in and we didn’t know if it had good reviews but the view was drawing us in. We order a pasta dish and a charcuterie board. Our meal was great, we even had the place to our self which was a plus.

Beautiful view
Exploring Cortona

Day 3: Vespa day

Vespa’s are a very typical way of transportation in Italy. So…of course we had to rent one for the day. The plan for day 3 was to rent a vespa and drive to Montepulciano and Pienza.

We hopped on our vespa and made a quick stop to get gas then headed to Montepulciano. Located in southern Tuscany in the province of Siena. Driving there was a once-in-a-lifetime experience. Rolling hills, vineyards and small towns.

We arrived in Montepulciano, parked our vespa and headed into the centre of the town. For all you Twilight fans, the filming for the seguel New Moon took place here. I didn’t know until after. The main site to visit is Piazza Grande, located on the highest point of the city and is where all events take place.

Taking in the view

We had packed some lunch. We found a bench where we could soak in the view and had a little picnic before heading to Pienza.

Pienza is considered the capital of pecorino cheese, because of its high quality. They even have a festival called “Fiera del Cacio” dedicated to Pecorino cheese. I know…only in Italy. As you walk around you can smell the cheese and are pretty much surrounded by it. Almost every other shop sells it. We picked up some Pecorino Cheese as well as homemade pasta. Lets just say we were planning supper for that night! Pienza is a very charming and romantic town.

Pecorino cheese
and…more pecorino cheese

Day 4: Car day

We decided to rent a car to go to some cities a bit further out. I got ready while Collin went to pick up a cappuccino and the car. We had planned to go to Assisi and Perugia.

Assisi is a very religious town. One of the main sights is the Basilica of Saint Francis of Assisi. As you start driving up to Assisi the first thing that stood out to us was the color. It looked as if the full town was all the same color a cream/stone color. It looked beautiful, we couldn’t wait to park the car and start exploring.


First stop, the St Francis of Assisi Basilica. It has been a UNESCO World Heritage Site since 2000. Located in the town where St. Francis was born and where he died. As you walk up to the basilica you can see the stores filled with catholic statues, rosaries and crosses. It is a beautiful basilica made of an upper and lower church as well as a crypt. As you walk around don’t be surprised. It is common to see monks as you walk around.

Our next stop, Perugia. It is home to the University of Perugia one of the oldest universities in Italy. It attracts lots of international students. We didn’t get to do or see much. We hadn’t planned much before arriving we just wanted to walk around and explore. Everything seem closed and the streets where quiet. We are still happy we went but we would pick a different city next time or have a plan before arriving.

Day 5: Making our way to the next city

Woke up and sat outside taking in the beautiful view before heading to the train station. Our Airbnb host was amazing, we weren’t expecting his wife to show up at our door willing to drive us to the train station. We are so thankful she did!

Excited for our next stop we hop on the train and 4 hours later we arrived in charming Venezia.

If you are planning to go to the Tuscany area and do different road trips. We highly recommend having Cortona as your home base. It was pretty central and has lots of cute restaurants and cafes.

Get $45 CAN towards your first trip by using our invite link www.airbnb.com/c/cglass21


Assisi houses with overlay text perfect itinerary tuscany

Leave a Reply

Your email address will not be published. Required fields are marked *

%d bloggers like this: