Exploring Tuscany: A 3 Day Itinerary

It was my first time exploring Tuscany by car and not only was it a welcome change from the usual way I traveled in Italy (train) but also more relaxing!! There are many ways to see a place, but if you have the option, hiring a car is the best one. Not only will you experience more but also see parts of the region that are not possible to visit otherwise by train. A road trip through Tuscany came to me at the right time and it was probably what had been on my wish list since long too!

Exploring Tuscany: A 3 Day Itinerary

Day 1:

Radda in Chianti

While most people prefer to see Italy in all it’s glory in the summer, I feel Italy is equally pretty in Winter and I feel fortunate to have enjoyed the pleasures of the countryside in that time. One such place I enjoyed was Radda in Chianti.

A beautiful medieval town well placed between Florence and Siena, Radda in Chianti is a popular Summer destination for everyone but in Winter you could count the number of people on the street. The tiny hamlet is surrounded by distinctive walls. Only a few steps in front of you is it’s Palazzo del Podestà, now an office. However you can go inside and ask for a tour to it’s jail cells. It is worth it!

There is a lift that takes you to the lowest part of the Palazzo where you can see how the prisoners lived. It is quite eerie being in a cell where you could barely breathe but seeing the way people were held captive is an experience in itself. This was something completely out of my comfort zone and even though I did see it, I was so so glad to be out of there.

Exploring Tuscany: A 3 Day Itinerary
Exploring Tuscany: A 3 Day Itinerary

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Exploring Tuscany: A 3 Day Itinerary

Radda in Chainti is very charming but my highlight of the visit was not the prison but meeting a lady doing her embroidery. She was busy stitching when I arrived in her store and it was a pleasure to see her doing work ever so smilingly.  Go and buy something from her like I did and don’t miss that smile! This store is right next to Palazzo del Podestà so you can’t really miss it. A few steps below this one is Decori nel Tempo– a modern art studio where the owners (a young couple) make pottery and hand paint them keeping the mark of the black rooster (a symbol of Chianti) alive in all their designs. Another great find!

There is no shortage of place to eat in this little town and I settled at the very popular La Bottega di Giovannino to gorge on some traditional pici pasta with wine.


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Day 2:

Pienza and Montepulciano

On the second day, I drove all along Val d’Orcia! An extremely popular Tuscan landscape dotted with the most prettiest scenery, Val d’Orcia is a UNESCO World Heritage Site since 2004. It is one of the most stunning strips of land I have ever seen in my life and it was really a dream to be there and watch the green unfold in different ways.

Check out this great tour of the Val D’Orciao

Pienza sits on a corner of the Val d’Orcia and is known for it’s pecorino (cheese made from sheep) and romantic streets. The town’s jaw dropping Cathedral and views of the valley are enough to give you a high. Even on a winter day, it was full of tourists! Despite there being stacks of pecorino everywhere, there was no place available for lunch. Maybe it was due to it being a Sunday but in any case I opted for a cheese platter (because why not!) at the Bar by the Duomo.

Exploring Tuscany: A 3 Day Itinerary
Exploring Tuscany: A 3 Day Itinerary
Exploring Tuscany: A 3 Day Itinerary
Exploring Tuscany: A 3 Day Itinerary

Wandering around the town of Pienza and it’s many stores was a lot of fun. You can spend as much time in it’s tiny streets but beware- it is a real touristy town. I want to go back again but all I want are those cheese boards! That smell was heavenly!

If you can’t hire a car, book this tour of Pienza and Montepulciano that stops for a wine tasting!

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My next stop was to the town of Montepulciano. I was told that there was a one of a kind Torinese styled Cafe in the town with a view to die for! While it was exceptionally chilly that evening, I took a peek at the famous  Caffè Poliziano and it’s little balcony. What a place to sit and have your drink!!

Exploring Tuscany: A 3 Day Itinerary
Exploring Tuscany: A 3 Day Itinerary

Other than that, Montepulciano is like stepping in a movie set where everything is about griffins and lions being the coat of arms. What a town!! Move along a little further from it’s historic centre (it is quite a climb) and visit the wine cellar of Cantina De’ Ricci to sample a few Tuscan specialties.

Sigore Ricci is a wonderful man and knows the land like no other. Book a tasting with him and his wife and you’ll surely come back with an appreciation for wine cellars and the Ricci family of Montepulciano!

Exploring Tuscany: A 3 Day Itinerary
Exploring Tuscany: A 3 Day Itinerary
Exploring Tuscany: A 3 Day Itinerary

Day 3:


On my last in Tuscany, I had the pleasure of seeing Siena with Federica Fiscaletti from TouringSiena. She gave Barack Obama and Michelle Obama a tour in 2017 when they visited Siena. I’m not only honored but also grateful for the experience. It was an honor to be with yet another passionate individual and hear of things you wouldn’t know from a guide book! Federica takes tours across Tuscany and customizes them based on your time and interest. I only had a few hours in Siena, so she was most flexible and accommodating to ensure I saw something new. (I had visited Siena earlier in 2015).

Federica is extremely informative and told me about the Palio and the different examples of enmity between Siena’s contrades. She took me towards a side of Siena mostly missed by tour guides and one of the highlights was the mention of Bottini- an old system of tunnels which you can visit as a guided tour in spring and autumn. This historic system was even mentioned by Dante in his writings. For more information on this intriguing tunnel system, check La Diana, a voluntary organization giving tours of the Bottini.

Exploring Tuscany: A 3 Day Itinerary

Nonetheless, a good time. I stopped for lunch bang in the centre of Siena at Osteria La Mossa and I was delighted to see more Tuscan wines and pappardelle for the day’s menu. Osteria La Mossa has a very old styled slow service but their food is exceptional!

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Exploring Tuscany: A 3 Day Itinerary
Exploring Tuscany: A 3 Day Itinerary

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Exploring Tuscany: A 3 Day Itinerary

As you can probably see, I wasn’t in any hurry to rush since I wanted to enjoy my time in Tuscany. Usually, I traveled to these towns until early evening and left the rest of the evening for relaxation and eating more Tuscan specialties. I hope this 3 day itinerary gives you a sense on some general ideas on places to see and eat in this part of Tuscany. If you have any specific questions or tips, let me know in the comments! You can book a car via AutoEurope


Where to Stay:

I stayed in Montestigliano and couldn’t have had a better base to be in the centre of Siena and Florence and yet a little far from city life. If you are looking for a place to stay in Siena, check these fabulous Airbnb apartments and also Grand Hotel Siena.



I received a tour from Federica Fiscaletti, a wine package from Cantina De’ Ricci and a discount from Osteria La Mossa in exchange for an honest view on this post. However, as always, all opinions are my own.

60 thoughts on “Exploring Tuscany: A 3 Day Itinerary

      1. I am doing OK thanks. Back in Australia. My friends from Hawaii are arriving here soon to stay with me for 2 weeks, I am so excited. Not sure where to next this year but next year is a big year of travel. Hope you are doing well also. x

  1. Outside of the main tourist season is always a great time to visit anywhere, far from the madding crowd. It’s a lovely itinerary and great photos but equally you could spend three days in Siena.

  2. Hey Ishita, I studied abroad in Siena and I felt the same way about getting lost in its history! There’s so much background knowledge that is necessary to understand the city. It would take a lifetime! Great post 👍

  3. Reading this was so much fun since I was just in Siena last week! It made me so nostalgic! We really fell in love with Tuscany, and now I have more place to add to my itinerary for next time 😉

  4. Nice visit and great photos to illustrate it. The first time I rented a car in Italy was last year, and you’re right, it’s so liberating. And there are so many places that you just can’t go without it, and you don’t have to try to figure out the impossible with trains and buses. However, I’ve had some interesting encounters on public transportation to places where tourists don’t take public transportation.
    Good idea to do some traveling on the off-season – great way to actually see who lives there.

    1. Grazie Karen. exactly. You can drive for hours without having to worry of stops, pack a few things to eat, picnic on the way. I am so glad I did it! How are you doing??

      1. I’m doing well, working on a book about Basilicata and have some traveling coming up in July – to Scandinavia and then to Asia for the first time for my nephew’s wedding in Japan!

        1. How wonderful!! So much to look forward to. Good luck on the writing, sounds very intriguing. I still have your book on my wish list 🙂

  5. Ah Toscana, I love it and miss it so! What an amazing 3 days you had there. I absolutely loved Montepulciano and now I want to see Pienza as well…one to add to the list for sure! Also, I need to see some of those black rooster creations at Ceramiche Rampini too! Great post and photos of the countryside and the food! 🙂 Makes me long to be there yet again.

  6. wonderful to read this post. This is my dream to visit more of Tuscany . I have been to Pisa, Lucca, Florence but not yet the places where you went. Great pics.

  7. I never tire of Tuscany. There are so many beautiful towns to visit. I loved Montepulciano. When we were there last, they were actually filming in the main square, the tv series about the Medici family with Dustin Hoffman. We missed seeing the cast as we were there over the weekend and the cast were on a break! Still got to see all the props and sets around the piazza though 🙂

  8. You are right, winter and spring are the best seasons for visiting Italy. I always escape summer. Thank you for the excursion. It was interesting to compare our impressions.

  9. Love, love, love Tuscany and hearing your stories and seeing the gorgeous places through the photos makes me so envious that being single have so much perks when it comes to moving about. LOL!

      1. Shift as in parental status? Hahaha😂. My 16-year old went to Paris on her spring break and two weeks after she came home, she went to Milan and Venetiè leaving her cat for me to baby sit. I am now planning to go to Barcelona in the summer before she outdo me with her own travels! And yes, there’s the caaaaat!

          1. There’s a huge difference being a tourist and living in Italy but Tuscany is a picture-perfect place to retire! Other than that, I’ll suffice myself reading your Italian adventures and dream that I am there too. Cheers!

          2. Oh yes. From your past comment I thought you meant “moving about” meant shifting to Italy 😉 I didn’t know you meant me. PS- I am not single 😉

  10. Great post and photos!
    I much prefer the winter or out of tourist season for Italy as it has become just too popular. Even down in Calabria I’m starting to see more tourists than 2 years’ ago. The word is out!

    1. I think people really mistake Italy for being a summer country. There is so much to do in winter too. Calabria is getting popular!!

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