Italy Travels: Two Days in Tuscany

Italy Travels: Two Days in Tuscany

At the last-minute before we went on our trip, we decided to spend a day or two in Tuscany. After some research, we decided that exploring the Chianti region of Tuscany made the most sense as we were coming from Florence.

We rented a car (which I’ll detail down below) and thought we’d take Route 222, also known as the “Chianti Road” down to some smaller towns we wanted to visit – Greve, Radda, Castellina, Panzano.

Italy Travels: Two Days in Tuscany

It’s not a real vacation when you have one day that goes wrong – and our first morning of our Tuscany day was that day.  (I can’t have you all thinking that our vacations go according to plan!) After the long and tedious car rental shuffle, we took a few wrong turns and missed the Rt. 222 Chianti Road altogether. Driving in a foreign country is always an adventure, especially when somebody (*ahem, me) is terrible at directions.

Italy Travels: Two Days in Tuscany

Eventually we figured out a way down to Greve in Chianti, our first stop. Just driving through the region was breathtaking. The Chianti region is almost mountainous compared to the classic undulating hills of Val d’Orcia.

The first town we stopped at was Greve – one of the larger villages in Chianti. And, in our opinion, not very exciting. Nearly everything was closed due to the town market – which was not as exciting as it sounds. More like the locals chance to stock up on underwear and dish soap.

As you can see, our day is Tuscany was not shaping up to what we wanted it to be. We decided to change course and head to our hotel early. This ended up being our best decision all day!

Italy Travels: Two Days in Tuscany

via Il Borghetto website

Italy Travels: Two Days in Tuscany

We stayed at Il Borghetto in Montefiridolfi, a very small town south of Florence. Il Borghetto is an inn on a working farm – also called agriturisimo, or agricultural tourism.

We LOVED it. It was an accidental find that I stumbled across online – I was sold!

Italy Travels: Two Days in Tuscany

We spent the afternoon walking around property of the hotel – the caretaker said that nothing was off-limits. So we spent the afternoon strolling through olive groves and vineyards, and even explored an Etruscan tomb. (<— There’s a sentence I never thought I’d say.)

Italy Travels: Two Days in Tuscany

The rest of the afternoon was spent on the terrace of Il Borghetto drinking coffee and reading, all while taking in the spectacular views everywhere. Italy Travels: Two Days in Tuscany

The staff at Il Borghetto was lovely, and if we ever find ourselves in Italy again we will definitely return. We even tried to cancel our hotel the following night so we could stay an extra night! (Darn those cancellation fees)

That evening we went to dinner in the town of Montefiridolfi. As the Il Borghetto Innkeeper put it, “there’s one road that leads to the one town square. There’s one restaurant in the square. If you miss it, let me know because that would mean you are amazing.”

Our dinner at A Casa Mia was definitely one of our top dinners of our vacation. There are only five tables and once you are there the table is yours for the night.

Italy Travels: Two Days in Tuscany

Everything about A Casa Mia was authentically Italian – the food was delicious, the tables were worn down after years of happy eaters. If you want cheese on your meal, they had you a hunk of cheese and a grater. The same person takes your order, cooks the meal and serves it to you.

Italy Travels: Two Days in Tuscany

We tried vegetable tempura for the first time – I wasn’t expecting much from fried vegetables, but goodness gracious were they delicious. Definitely don’t miss it if you are in Italy!

The following day we were originally going to head Lucca, but we decided to skip it and try our hand again at exploring Chianti. We visited Panzano, Radda and Castellina, but spent most of the afternoon taking small back roads getting from place to place and taking in the sunshine.

Italy Travels: Two Days in Tuscany


Panzano is a tiny town with amazing sweeping views of the valleys. There’s not much to the tiny town, but certainly worth seeing.

Italy Travels: Two Days in Tuscany


This was the clear winner of towns for my husband. Radda is an old town. There are a few shops to poke your head into in Radda. The town is also small and sleepy.

Italy Travels: Two Days in Tuscany

Italy Travels: Two Days in Tuscany


Castellina would warrant an afternoon of exploring. Known for the Via del Volte, a covered medieval walkway, the town is sizeable with many shops and restaurants.

Castellina is particularly popular with wine lovers. We didn’t get a chance to linger at any wineries, but there were many beautiful ones in Castellina I would have loved to check out!

Italy Travels: Two Days in TuscanyItaly Travels: Two Days in TuscanyItaly Travels: Two Days in Tuscany

Our two days in Tuscany were so peaceful and relaxing! The area of Chianti is scenic and beautiful. We spent the better part of our time in Tuscany just driving around on the back roads. The food and wine were delicious.

There were wineries everywhere that were open for visiting, maybe we will do that next time! We had originally planned to stop by one, but I think a better plan would have been to make a reservation at one before you are there.

Getting to Tuscany

Tuscany is one of those places you simply can’t rely on to visit with public transportation. That’s the beauty of it I suppose! No trains, few buses, and small towns.

We rented a car from the Hertz at the Florence airport. After hearing many nightmare stories about driving in Italian cities, we decided to bus outside of the city, pick up the car there and avoid city driving altogether.

In theory, this was a good idea. But, I won’t lie. The process of walking to the station, taking a bus to the airport, and then waiting for an airport shuttle to take us to the rental cars was a pain and took forever. In hindsight, we maybe should have saved the bus fare and paid a cab to take us directly to the rental cars at the airport.

Also – rental cars in Italy are as much of a racket as they are in the U.S. The process takes forever and there are charges on top of charges. BUT, it’s cheaper than signing up for a Tuscany bus tour. So if your heart is set on seeing Italy, it’s the best way.

Well, that’s it for my Italy travel recaps! I still have a post coming on packing in a backpack, but until then, thank you for reliving my trip with me. It was a dream and everything hoped it would be!

Have you been to Italy?
What is your favorite part of Italy? How can you possible choose!?!?

6 thoughts on “Italy Travels: Two Days in Tuscany

  1. It looks wonderful. I have never been to Italy. If I go I would like to go to Tuscany. It sounds so romantic. The buildings are old and beautiful and the food sounds delicious. So glad you had a lovely time and wanted to share with us.

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