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!! Exploring Tuscany by car is simply marvelous and I’d love for you to enjoy and bookmark this 3 day itinerary for your future trip to the region.
Exploring Tuscany: A 3 Day Itinerary
There are many ways to see Tuscany but only after being in the car did I realize, it was the best ways to see unusual explored towns. Hiring a car is the best idea because you will end up seeing all the parts of Tuscany not connected by train. went on a lovely winter afternoon and while most people prefer to see Italy in all it’s glory in the summer, I think Italy is the the countryside is equally pretty!
Day 1: Radda in Chianti
Your first stop should be the Tuscan town of Radda in Chianti, a medieval town well placed between Florence and Siena. Radda in Chianti is a popular summer destination for everyone but in winter you can count the number of people on the street.
The tiny hamlet is surrounded by distinctive walls and houses the municpal building called Palazzo del Podestà. The ancient palazzo has prison cells from the 17th century. If you go inside and simply ask for a tour of the jail cells, there’s a lift that takes you to the lowest part of the Palazzo. You would be able to see the low lying cells where they kept the prisoners and as eerie as that sounds, it will something unique to see in Tuscany. I could barely breathe as it was something completely out of my comfort zone!!
Radda in Chainti is very charming and full of boutiques and restaurants. While walking around town, I met an elderly lady working on her embroidery. She was busy stitching when I arrived in her store and simply smiled when I bought a pretty necklace from her. Her store was right next to Palazzo del Podestà so she was right in the centre but there was not a single tourist apart from me.
Also in Radda in Chianti is a modern art studio called Decori nel Tempo. Owned by a young couple who are passionate about pottery and hand painting, Decori nel Tempo keeps the symbol of Chianti alive in all their designs. (its a black rooster!)
Day 2: Pienza and Montepulciano
On the second day, drive 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 a dream to be there and watch the green unfold in different ways.
One of the most popular towns in this part of Tuscany is Pienza which 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, Pienza is busy and on Sunday I didn’t find a place for available for lunch. So I opted for a meat and cheese platter (because why not!) at the Bar by the Duomo. Pienza is extremely picturesque and smells heavenly of pecorino cheese! (but all in all a very touristy town!)
Pienza is also very close to the Tuscan town of Montepulciano which has a unique central piazza and delicious wine. Montepulciano is like stepping in a movie set where there are griffins and lions on the coat of arms. The historic centre is quite a climb but simply worth it. Caffè Poliziano and it’s little balcony is a great place to sit and have your drink!! This is a one of a kind Torinese styled Cafe.
The wine cellar of Cantina De’ Ricci are an excellent place 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!
Day 3: Siena
Driving in Tuscany is simply beautiful and right out of a fairy tale. On day 3 you should visit the old town of Siena. I booked a tour with Federica Fiscaletti from TouringSiena who had also given a cultural tour to Barack Obama and Michelle Obama a tour in 2017!! It was an honor to be on a tour with her! She is passionate about Tuscany and very flexible. She even customized the tour as per my time and needs! (Thanks Luisa!) Since I only had a few hours in Siena, she accommodated to ensure I saw something new (I had visited Siena earlier in 2015 as well). Federica is extremely informative and told me about the Palio and the different examples of enmity between Siena’s contrade.
She took me towards a side of Siena mostly missed by tour guides and told about Bottini, an old system of tunnels. There are guided tours of this historic system tunnel system, check out La Diana, a voluntary organization giving tours of the Bottini.
Siena is such a wonderous place to walk around and enjoy. Stop for lunch in the centre of Siena at Osteria La Mossa and try their Tuscan wines and pappardelle. Enjoy the old styled slow service and exceptional food!
In 3 days, my friends and I explored Tuscany at our own pace. As you can probably see, there was no rush. We started in the morning to visit these towns and left the rest of the evening for relaxation and enjoying 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.
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www.8rent.aeAugust 6, 2019 at 9:58 pm
Thankfulness to my father who told me on the topic of this weblog, this web site is
Image Earth TravelJuly 11, 2018 at 12:24 am
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!
ItalophiliaJuly 11, 2018 at 12:08 pm
I think people really mistake Italy for being a summer country. There is so much to do in winter too. Calabria is getting popular!!
ejsnaJune 21, 2018 at 3:35 pm
Oh, dear Ishita, you’re doing great!😘
ejsnaJune 20, 2018 at 7:50 pm
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!
IshitaJune 20, 2018 at 9:53 pm
Thank you dear 🙂 So happy to know that. LOL!! Haha.. are you planning to shift? 😉
ejsnaJune 20, 2018 at 10:20 pm
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!
IshitaJune 21, 2018 at 12:04 pm
No I meant settling in Italy 🙂 that’s cool! Enjoy your travels
ejsnaJune 21, 2018 at 1:49 pm
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!
IshitaJune 21, 2018 at 2:13 pm
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 😉
Victor TribunskyJune 18, 2018 at 2:53 pm
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.
IshitaJune 18, 2018 at 2:55 pm
Happy to have Victor …I loved winter in Italy. very special…:)
pamelaallegrettoJune 16, 2018 at 1:57 am
It’s always a delight to read your blog posts. Although, they do make me feel quite homesick.
IshitaJune 16, 2018 at 10:50 am
You are so kind! When are you traveling next??
a mindful travelerJune 14, 2018 at 6:16 pm
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 🙂
IshitaJune 15, 2018 at 10:48 am
Me too. And despite being so touristy it somehow retains the charm 🙂 How cool for you! I’ve seen that show. xx
a mindful travelerJune 15, 2018 at 3:15 pm
It was really cool. I watched it too back home at least 8 months after we returned, and recalled fondly of the the sets we saw. Good show. X
france55June 14, 2018 at 1:52 am
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.
IshitaJune 14, 2018 at 11:31 am
Thank you so much for reading. Those are some great places! x
hopelesswondererJune 14, 2018 at 12:06 am
this place looks adorable!
IshitaJune 14, 2018 at 11:24 am
Thank you 🙂
Drew YoungsonJune 13, 2018 at 6:29 pm
It is good point of view of the place where i live, i think it is well write article.
IshitaJune 13, 2018 at 6:30 pm
So happy you agree Drew 🙂
Tony StaffaroniJune 13, 2018 at 6:21 pm
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.
IshitaJune 13, 2018 at 6:31 pm
Just make a wishlist already 😂 I’m hoping for your return soon …! April 2019 😍😍 thank you for reading again x
beshelleyJune 13, 2018 at 4:26 pm
You make Italy come alive for me, a journey I may never get to make on my own. Thank you for wonderful pictures of Italian life.
IshitaJune 13, 2018 at 6:03 pm
You are so kind!! Thank you 🙂
TanjaJune 13, 2018 at 2:28 pm
I quite like Montepulciano and Siena:)
IshitaJune 13, 2018 at 2:57 pm
Good choices and thanks for sharing on Twitter 🙂
ravenhawks magazineJune 13, 2018 at 1:36 pm
Reblogged this on ravenhawks' magazine and commented:
IshitaJune 13, 2018 at 1:40 pm
Thanks for the share 🙂
karenincalabriaJune 13, 2018 at 12:32 pm
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.
IshitaJune 13, 2018 at 12:34 pm
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??
karenincalabriaJune 13, 2018 at 1:01 pm
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!
IshitaJune 13, 2018 at 1:03 pm
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 🙂
KellyJune 13, 2018 at 12:32 pm
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 😉
IshitaJune 13, 2018 at 12:33 pm
Aww thanks Kelly. I can imagine as I got nostalgic while writing only! There’s always so much to see :O
thewonderer86June 13, 2018 at 12:00 pm
Gorgeous! I especially love your first shot – the Tuscany of dreams!
IshitaJune 13, 2018 at 12:09 pm
I know right, that is quintessential Tuscany. Very dreamy!
unsavvytravelsJune 13, 2018 at 11:16 am
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 👍
IshitaJune 13, 2018 at 11:47 am
That must have been ab experience 😍😍 thanks for reading dear
Debra KolkkaJune 13, 2018 at 10:26 am
We often drive through this gorgeous part of Italy. I love it in any season.
IshitaJune 13, 2018 at 10:29 am
You are so lucky to be there so often!
IngridMadisonAveJune 13, 2018 at 9:51 am
Simply gorgeous! The food pictures are spectacular. Thanks for sharing! xx
IshitaJune 13, 2018 at 9:52 am
Thank you for reading. Have a lovely day Ingrid 😊
IngridMadisonAveJune 13, 2018 at 9:53 am
Same to you 💋
Lynette d'Arty-CrossJune 13, 2018 at 3:24 am
I agree that travelling in Italy is also great during the shoulder seasons – I in fact prefer it. And you went to Siena – I love that city. 🙂
Great photos. 🙂
IshitaJune 13, 2018 at 9:21 am
Thank you dear! It was my second time in Siena 😍
ShereeJune 13, 2018 at 2:47 am
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.
IshitaJune 13, 2018 at 9:20 am
Absolutely! Siena is such a treat always but since I had been there earlier, I chose other towns.
DarleneJune 13, 2018 at 2:01 am
Wow!! A great 3 days. The photos are incredible and you seem to find the best in every place you visit.
IshitaJune 13, 2018 at 2:02 am
Thanks so much 😍 🙌 it’s the people who help me to find these places.
ChrissyJune 13, 2018 at 2:00 am
Beautiful photography! Makes me want to travel to this destination! ✈️🍷😃😍
IshitaJune 13, 2018 at 2:00 am
Thanks so much Chrissy!
ChrissyJune 13, 2018 at 11:46 am
You’re welcome! 😁
Lyn DouglasJune 13, 2018 at 1:48 am
How simply fabulous Ishita. I have done it a few times now and love it, really it is the only way to explore Tuscany. Your photos are gorgeous. Lyn x
IshitaJune 13, 2018 at 1:49 am
Thank you Lyn! How are you?? Are you still abroad? Have a great day x
Lyn DouglasJune 13, 2018 at 1:57 am
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
IshitaJune 13, 2018 at 2:01 am
That’s wonderful! Enjoy 🙂 I’m doing good too. No travel to Italy yet but I’ll keep you posted.
Lyn DouglasJune 13, 2018 at 2:48 am
Please do, I am always interested in your trips to Italy