The Dream Trip | Part 2: Cortona

day-to-day. eats. wandering.

The next leg of our trip took us to Cortona in Tuscany.  Cortona is about 2-1/2 hours north of Rome and we decided to rent a car versus taking a train so we’d have a little more freedom to explore.  Tuscany is BIG so we had a tough time choosing where to stay, but we decided on Cortona mainly because it didn’t seem too “touristy” and was still relatively close to the other cities we wanted to visit – – Siena, Montepulciano, and Chianti.  It also happens to be the city where the movie “Under The Tuscan Sun” was filmed which didn’t matter much to Michael, but secretly piqued my interest.  And to add to all of that, close friends had recently stayed there and raved about it so we thought, why not?

Check out our sweet ride, a Fiat 500.  Or a “cinquecento” as the Italians call it, according to my brother.  We got a little upgrade from the Fiat “Panda” we originally booked.  Yeah, we’d never heard of the Panda either.


Riding around in this thing was so much fun.  Michael drove while I navigated… with help from a GPS.  I don’t drive a manual well (or at all) and figured Italy wasn’t the place to learn.  People drive fast here!  And aggressively.  Good thing my husband isn’t afraid to do either of those things.  He fit right in on the autostrada!  He even tried keeping up with a Ferrari *insert eye roll here*.

We arrived in Cortona in the early afternoon and realized quickly that we’d have to pay close attention to the street signs.  These walled cities are a bit like a maze.  They have specific entrances and some roads that you DO NOT drive on.  An elderly Italian gentleman was neither amused nor helpful when we found ourselves on a narrow, pedestrian only street.  Thank God we had a tiny car and Michael’s a good driver.  Talk about a tight spot!

Cortona was everything the photos promised.  The city’s situated high on top of a hill and the views were incredible.

Church of Santa Maria Nuova



Tuscany is the complete opposite of Rome.  We had just experienced five days of hustle and bustle with lots of crowds, traffic, and noise and now found ourselves dropped into the quiet countryside.  The calm, sleepy countryside.  It was a little eerie at first how empty Cortona felt.  And it wasn’t by any means “empty,” but compared to Rome it was.  People were still tending their shops and restaurants and we saw a few other tourists wandering the streets, but it was definitely quieter than we anticipated.  We also arrived two days before Christmas, so we assumed most locals were on holiday.

We stayed at a super cute, well-kept B&B called “La Corte di Ambra.”  Our host, Sara, was incredible and gave us lots of suggestions for places to visit while in Tuscany.  She is originally from the region and opened the B&B with her mother.  You can tell they take so much pride in their business.  She enjoys when foreigners stay so she can practice her English and we were happy to help her!  It was a bit of a relief as she was pretty fluent already, so we leaned on her for language help and directions.

It truly helps to learn a bit of the local language before you go.  Or bring a vocabulary & phrase book, which we did.  I read through it in our hotel rooms and before we went out so the words would be fresh in my head.  Though many people speak English, it goes a long way if you try conversing in their language first.



Il Cacio Brillo – A cool bar/restaurant we found in the nearby Piazza Signorelli.  We were in a basement surrounded by bottles of wine.  Heaven.


Piazza della Repubblica

The next day we drove to Montepulciano and Pienza.  As it was Christmas Eve a lot of the shops and restaurants were closed, but we still enjoyed walking around and seeing how each city differed from the other.  All the photos below are from Pienza as I apparently forgot to take pictures while in Montepulciano.  It was a brief stop anyway =/

Leaving Cortona on a foggy morning in the valley.
Husband driving our cinquecento!
Beautiful countrysides.
Pienza Duomo
Ancient well in the Palazzo Piccolomini





It’s true what they say, photos don’t do it justice.
Decided to stop at a park along the road to take photos – – didn’t realize it would give us this view.


Selfie in the Tuscan countryside.

We had dinner reservations at a restaurant named La Bucaccia in Cortona on Christmas Eve.  We were a little nervous walking there as the streets were almost empty and a lot of the other restaurants looked closed for the night.  We’d made the reservations via email from home and didn’t really have much in the way of a confirmation!  To our relief, they were open and we were greeted with cheek kisses by the very animated gentleman host.  Who also decided to nickname me “Blondie” the rest of the night… I think it’s safe to say that was equal parts complimentary and mocking.  But he was very attentive and the food, service, and ambiance were excellent.

La Bucaccia


Some prosciutto and chicken liver pate. We love food.
Steak in a red wine sauce. We had a few versions of this while in Italy.


Something happened the next day that is definitely one of the highlights of our trip.  And of course, it involves food.  On Christmas day we had lunch reservations at a restaurant called Osteria del Teatro in Cortona.  Lunch because their dinner service was already fully booked.  Something else to note if you plan to travel here – – Italians eat late compared to American standards.  Lunch usually happens around 1-2pm and dinner can start anywhere from 8-10pm.  Breakfast is not a thing here.  Usually just a cappuccino or espresso, maybe a pastry, and that’s it.  By this time we’d become accustomed to the standard and came prepared with an appetite to our 1pm reservation!  We knew we were having a prix-fixe menu, but little did we know we were walking into an eight-course meal.  EIGHT.  Courses.  Are you kidding?!  It was the best Christmas present ever!!  It took four glorious hours to finish and you just about had to roll us out of there when we were done.

The best part is that we were some of the first patrons to leave.  The restaurant only booked one lunch reservation time, which meant no one was waiting at the door.  And because of that no one felt rushed to finish so the staff could “turn” the table.  We were able to fully enjoy the cuisine and the company we were with.  I sure wish we did that more in the States.

I didn’t take a photo of every course, but here are a few.  And I’ll have you know I wasn’t the silly American taking photos of my food.  I saw tons of Italians (and French) do the same thing, I swear!  Everything was soooo good.  We’ll dream about this meal for years.

Osteria del Teatro


The prix-fixe menu. You can count six courses, but the amuse bouche wasn’t listed and we received both Primi Piatti!
Primi Piatti – Tagliolini
This was dessert. The booziest cake known to man.
A really great bottle of white that I hope to find again soon.

On our last full day in the area we traveled to Siena.  One of the largest walled cities in Tuscany.  It was definitely big and we ran into way more tourists than we’d seen during the last three days combined!  Again, I’m sure Michael and I missed most of the historical significance of these places, but we were having so much fun just checking out the architecture and envisioning what day-to-day life used to be like in these cities.

Driver and navigator/selfie-taker.
Palazzo Pubblico and the Piazza del Campo, Siena



The Fonte Gaia
Pizza and a panini for lunch.



Battistero di San Giovanni
Walking to the Siena Cathedral (Cattedrale Metropolitana di Santa Maria Assunta)




Siena Cathedral
Obsessed with these streets.

Loved, loved, loved our quiet stay in Cortona and visiting all of the other nearby cities.  I still can’t believe we were there!  After going through these photos it’s hard not to get a little sad, but I do selfishly blog these adventures so I can re-live them over and over again.

Looking up at Cortona on the hill.
Church of Santa Maria delle Grazie
Above the clouds.

Florence is up next with a quick pit stop in Chianti – – stay tuned!