My First Italian Hilltown Experience: Hello Cortona!

When in Italy, people usually have these more popular places in mind such as Milan, Rome, Venice, Florence and of course – Tuscany. All these places sound lovely and a must-visit so this blogpost is about my first ever experience in the Italian countryside – a visit to a quaint and charming hilltown in Cortona, Tuscany. Best to be read with a wine glass in hand!

Hello, Cortona!

Cortona, Tuscany – Fast Facts

How to get there (from Manila, Philippines)

Name of Airport: Linate Airport, Milan

How To Get To Cortona, Tuscany from Milan (via car hire):

We landed in Milan which is not exactly near Tuscany honeymoon road trip. We picked up a car from Milan, our first stop was Lake Maggiore (read about it here), then Lake Como and thirdly, Venice. Right after our Venice trip (which you can read about here), we drove straight to Cortona, Tuscany!

Highlights: Honestly, I loved the drive on the way to Cortona. The small towns you pass by as you cruise along the roads of Tuscany. As you approach Cortona, you can instantly see it perched up on the hillside which was very exciting. When you arrive in Cortona, you’re on a hilltown in Tuscany and its sooo beautiful!

Currency: Euros

Time of travel: Around June-July (Summer season, for sure!)

Out of all the places in Tuscany – why Cortona? We were actually invited by my brother-in-law and his partner to come join them in the 2-bedroom apartment the had booked. I honestly had no expectations other than the fact I was looking forward to see ANY part of Tuscany. I was instantly inspired and excited after watching one of my favorite movies, Under The Tuscan Sun!

Upon driving up to Cortona, it was such a treat to see the whole of Valdichiana as you go up the hill. The roads are built so steep and narrow that there is actually only ONE gate where cars are allowed to enter Cortona because the city is surrounded by wall. This was actually a rookie mistake we did because I was a bad designated navigator I failed to read the fine print so Nick ended up driving through a gate NOT allowed for cars and it was a nightmare but hey – we made it!

The initial thing I noticed about Cortona is its like a medieval town and it’s so charming! There is a main square in the center, a theater and a beautiful church. The town comes alive in the evening where the locals congregate in the main square. The main street called Via Nazionale (the locals still refer to it by its older name of Ruga Piana) is where you’ll see most of the restaurants, cafes and shops. We would just book a local restaurant, sit outside al fresco, enjoy the scenery and people watching – it makes time go by so quickly.

I know it’s usually a given that everywhere in Italy (or Europe), the food is great, but what made my Cortona experience more special was the people we met. To have a flavor of what the town has to offer, through Hilltown Tours, we arranged a walking food tour around Cortona to try some of the local delicacies.

It was a day-filled with yummy pizza, cold cuts, cheese paired with wine, gelato (a must when in Italy!!!) – we went home with happy tummies. This tour was capped off with a lovely meal in Ristorante Ambrosia. It almost felt like a “Meet The Neighbors” as everyone was so warm and accommodating. I really appreciated the tour Hilltown Tours arranged because they introduced us to such a personal part of Cortona we wouldn’t have experienced if it weren’t for them.

We enjoyed the food tour so much we even dined in Ristorante Ambrosia on our last evening in Cortona. The food was impeccable, the wine was fabulous and Matteo and his partner were so accommodating! Thank you Cami of Hilltown Tours for giving us such a fun food trip and we will definitely book a table again with Matteo of Ristorante Ambrosia on our next trip.

While in Cortona, we did a day trip in Siena. It was a lovely drive and if you’re not familiar, this is where they filmed a huge chunk of the movie Letters to Juliet – which is one of my favorite movies. Here you’ll see the beautiful Duomo di Siena, Piazza del Campo and Basilica Cateriniana San Domenico – all in one day!

I really enjoyed that Siena day trip, just walking around with a gelato in one hand and my husband in the other. Hehe! Tuscany has definitely earned a spot in my heart.

In Siena

At the end of each lovely day, we go back to our apartment just a stones throw away from Cortona’s main square. This 2-bedroom apartment was spacious enough for our luggage, fully air-conditioned (which I highly recommend when you visit Italy in the summer!) and the apartment interiors felt so modern and new. Each morning, we’d relax by the balcony, hearing the birds chirping and just admiring the scenery. It was really perfect! This apartment was booked through Hilltown Tours again. I highly recommend them if you have a trip to Tuscany!

About Hilltown Tours

A tour operating agency founded in 2008, Hilltown Tours offer villas from Italy and has expanded to cater to your needs in other European destinations. Aside from getting you settled with your accommodation, they also offer services such as popular day tours, sorting the transfers and even meals at home with a private chef – they can easily arrange all of this with your villa booking. How awesome is that? Michele and his team from Hilltown Tours is such a breeze to coordinate with and they genuinely suggest what works best with your itinerary. Planning our trip with them made it effortless!

For our next Italy trip, we will definitely book with them again – in fact we already have and we’re due to see them in July 2021! Wuhoo! To know more about them, check out their official website on or follow them on Instagram on via @hilltowntours. If you already have a set date and to simply check out available villas in Tuscany, you may also check this website which is handled by Hilltown Tours as well.

One of the most memorable parts was driving to Villa Bramasole – THE Villa Bramasole which was the actual setting of the film Under The Tuscan Sun. I was ecstatic!

Villa Bramasole from Under The Tuscan Sun!

Wandering around Cortona was almost like getting lost in those Beatrix Potter storybooks I read when I was growing up. Secret gardens, lovely interiors and pastel colored shutters. I’m definitely in-love!

My first hilltown experience AND first Tuscany experience was amazing. I definitely had a sense of what it was like to be under the Tuscan sun! I highly recommend Cortona as a stop in your next Italian adventure.

Ciao, Yuki