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Road Trip Plan for Tuscany: 14 Days

Road Trip Plan for Tuscany: 14 Days

Road Trip Plan for Tuscany: 14 Days

Are you busy planning an awesome road trip in the beautiful Toscana

You are probably wondering and stressing a bit about what to do exactly and where to go to....

Well, I have good news for you my friend! 

I just came back from a 14 day road trip in Tuscany and it was just amazing!

So now I would like to share all the details with you!

Itinerary for 14 days drive in Tuscany

Road Trip: Tuscany in 14 days  Map

Road Trip: Tuscany in 14 days  Map

Day 1: Fly to Pisa and pick up a rental car at the airport (we used Goldcar and we were really satisfied with their service). Pisa is a great start for your road trip, it has an airport and you can easily make a round trip in Tuscany and come back to Pisa to fly back home (without driving through the same places). 

Here you have 2 options, either visit Pisa now or on the way back, when you are returning home, we decided to visit Pisa on the way back. 

After picking up the car you can drive to Lucca. It's worth it spending the day in Lucca. The city is very nice and there are lots of things to see. You can spend the night either in Lucca or somewhere close. We stayed a little bit outside of Lucca in a very small village called Castelvecchio (Capannori).

A beautiful market in Lucca

A beautiful market in Lucca

Before starting with the itinerary, I would like to give you a friendly advice: learn a little bit of Italian before you go...If you know a bit of words and phrases it will be definitely easier to get around, especially if you are planning to visit places that are not so touristy.

Day 2: Drive to Pistoia and walk around the centre. It's not very big but it's still nice and worth a visit. If you want to do something different and avoid a bit the touristy areas, you can drive in the mountains and spend some quality time in the nature. The air is very fresh and clean, plus we were there in October so the views were stunning!

Sunny Pistoia

Sunny Pistoia

Don't forget to learn some useful Italian phrases that will help you get around! 

Day 3: Drive to the Chianti area also known as the "Wine region" in Italy. The landscape is just amazing, with vineyards and olive trees just everywhere and a lot of picturesque small villages. It's best to spend 3-4 days in Chianti, there are a lot of things to do: you can go wine tasting, you can visit all the small towns (there are many churches and museums that are definitely nice to visit), you can just drive around and enjoy the stunning views or be busy eating some delicious Tuscany food and drinking lots of Chianti!

A good location for housing is somewhere close to Greve in Chianti. From there you can easily access all the small villages and also go to Florence, which is just a 45 min drive away. It's definitely nice to rent a house or an apartment with some outdoor area where you can also cook something and drink a glass of red wine while looking at the beautiful vineyards.

The view from our garden

The view from our garden

Day 4: Spend the day in Firenze (Florence). There are a lot of things to see and do in Firenze: you can visit some of the main museums and art galleries like the Galleria dell'Accademia where you will find Michelangelo's famous David, you can visit the Uffizzi, where you can admire some of Italy's greatest masterpieces. Palazzo Vecchio and Palazzo Pitti are also a must see, Ponte Vecchio and Piazza del Duomo can't be missed! If you want to enjoy a beautiful view of the city you should go to Piazzale Michelangelo.

View from Piazzale Michelangelo

View from Piazzale Michelangelo

View from Piazzale Michelangelo

View from Piazzale Michelangelo

A very nice place for lunch is Da Vinattieri: a small sandwich shop that sells delicious schiacciate (typical tuscan bread). We ate there for the first time in 2011, when we were visiting Florence an we found it by accident, so this year we decided to go back and see if it was still there...Luckily the tiny shop is still there and it's still offering amazing food! 

Useful tip: When parking the car I would strongly suggest that you leave at the Parking Parterre, where the maximum daily cost is 10 euro. It's a 15 minute walk from the Duomo, so it's not very fast. In Florence, like in most of the cities in Italy you can't enter the city centre with your car because there is the ZTL (Zona Traffico Limitato) and you need a special permission. If you do it, you will get a fine, which obviously is not great. 

Day 5: It's time to explore the Chianti area. Visit Greve in Chianti, a lovely little village where is nice to drink a coffee or if you like meat you can visit the Antica Macelleria Falorni, situated in the main square. Very close to Greve, just a couple of kms away is the Castello di Montefioralle which is also worth a visit. 

Greve in Chianti's main square

Greve in Chianti's main square

Chianti's vineyards

Chianti's vineyards

Useful tip: If you are looking for a nice place to have lunch or dinner, definitely go to L'Osteria Rifugio del Chianti, a little restaurant with incredible delicious food, very reasonable prices and more than wonderful service!

Day 6: Continue exploring the Chianti region. You can drive first to Volpaia (my favourite village in Chianti)! The drive to Volpaia is very scenic and it's one of the most beautiful we saw during our trip:

The scenic drive to Volpaia

The scenic drive to Volpaia

Continue driving to Vertine and Gaiole in Chianti, two small towns that are nice to see and great for a short break (you can drink an espresso or a glass of Chianti)! The two castles: Castello di Brolio & Castello di Meleto are very beautiful and if you have some extra time try not to skip them.

Day 7: Next stop is Montepulciano! For those of you that don't recognise the name, this is a lovely small town not so far from Siena and it's famous for it's wine production. Best to spend there 1-2 nights. 

Piazza Grande in Montepulciano

Piazza Grande in Montepulciano

There are lots of things to do in Montepulciano but the one thing you shouldn't miss is wine tasting! There are wine cellars all over Montepulciano and the wine is just amazing...I recommend visiting the Cantina De'Ricci, it's the oldest cantina in the city, their wine is delicious and you can visit it for free!

You should also enjoy the sunset while drinking a glass of wine at the bar E lucevan le stelle (the wine bar has an amazing view over the Val d'Orcia):

Panoramic view  from Piazza di San Francesco, Montepulciano

Panoramic view  from Piazza di San Francesco, Montepulciano

Useful tip: If you want to enjoy a nice meal in Montepulciano, make sure to always book a table...A great small restaurant is Osteria del Contethe food is really good, the house wine is simply delightful and the prices are very convenient. 

Day 8: Drive to Cortona: a small charming town, just 45 mins from Montepulciano. If you are staying in Montepulciano, you should definitely go for breakfast at Caffè Poliziano. It's the oldest bar in town and it offers all kinds of delicious pastries.

When you arrive in Cortona, there are lot's of things to do and see. The churches are really old and beautiful, Piazza della Repubblica & Pizza Garibaldi are also a must-see. 

Piazza della Repubblica, Cortona

Piazza della Repubblica, Cortona

If you want to enjoy a typical tuscan meal, stop by Trattoria Dardano! The place is quite small, so definitely book a table before going. 

Day 9: Our next stop is SienaSiena is not very big but it isn't small either, so it's best to stay for 1-2 days. The main things to see are: Piazza Campo, il Duomo, la Basilica di San Francesco and the Centro Storico.

Piazza Campo, Siena

Piazza Campo, Siena

View from Basilica di San Francesco, Siena

View from Basilica di San Francesco, Siena

Te Ke Voi? is perfect if you want a quick lunch: they prepare very nice focaccia; La Vecchia Latteria has one of the best gelato in town (be careful because 95% of the gelaterie in the city center offer low quality ice cream); Caffè Nannini is a lovely pastry shop where you can drink a good espresso or even a Vin Santo (dessert wine from Tuscany). 

Day 10: Scenic drive in the famous Crete Senesi (southeast of Siena). This is a must-see in Tuscany and it is just amazing...Start driving from Siena to Asciano:

Panoramic view : driving from Siena to Asciano

Panoramic view : driving from Siena to Asciano

Panoramic view: driving from Siena to Asciano 2

Panoramic view: driving from Siena to Asciano 2

When you have reached Asciano you can continue driving to Pienza

Beautiful street on the way to Pienza

Beautiful street on the way to Pienza

Another beautiful view on the way to Pienza

Another beautiful view on the way to Pienza

A typical Tuscan house

A typical Tuscan house

Your next stop is Pienza - my favourite little town in Val d'OrciaPienza is very famous for it's pecorino and if you planning a visit, make sure not to skip the cheese tasting! The best way of exploring Pienza is to walk around and get lost! Walking around Pienza and admiring the stunning views over the hills of Val d'Orcia is priceless! 

Pienza's centro storico

Pienza's centro storico

Pienza's "balcony" that  looks over Val d'Orcia

Pienza's "balcony" that  looks over Val d'Orcia

View from Pienza

View from Pienza

A really good restaurant is Trattoria da FiorellaI can honestly say that this place is one of the best ones we visited during our trip! Their homemade pici (traditional handmade tuscan pasta) were absolutely delicious...Definitely recommended!  

On the way back to Siena, you can stop by Montalcino and taste some Brunello di Montalcino, one of Italy's best wines!

Day 11: There are a couple of options here: you can either move to San Gimignano or you could go closer to the seaside...We were feeling a bit tired of all the driving and walking around, so we decided to go somewhere quite, closer to the sea, where we can get some rest and quality time with each other. We found a really nice small airbnb in Orciatico - a really small village where there is almost nothing, except beautiful nature! When I say nothing, I really mean it - there is no supermarket, no hotels and there is only 1 restaurant which is open only in the summer - great if you want to get away from all the touristy areas!

Our beautiful house in Orciatico

Our beautiful house in Orciatico

From Orciatico, which is the hometown of Andrea Bocelli, you can drive to Volterra, it's about 35-40 mins drive and it's really nice. The centro storico is beautiful, you can walk to the Piazza dei Priori and visit the Palazzo Vitia gorgeous private residence in Volterra!

Volterra

Volterra

Day 12: We decided that we have seen enough of the gorgeous small tuscan villages and thought visiting the seaside would be a good idea - and it was!

First, you can drive to Cecina and walk on the beach the lungomare (seafront) is very pretty:

Cecina's lungomare

Cecina's lungomare

Then you can continue to Piombino, a lot of the boats to Isola d'Elba depart from there. The city has an old historical centre and the coast is just beautiful...

Piombino's coast

Piombino's coast

On the way back, we stopped at Bolgheri, a beautiful small village, that is famous for its wine. You can go wine tasting, stop by for a quick coffee or simply go for a walk...

Bolgheri's castle

Bolgheri's castle

Day 13: One of our last stops was Livorno. The city is quite industrial but it's definitely nice for a day...If you like seafood, this is the place! There are lots of restaurants where you can enjoy some fresh fish meals. One of them is Stuzzicheria di Mare - it's also a shop, so if you want to buy something and cook it yourself, this is the place! Another one is Cantina Senese - you should book in advance because it's very busy. At first, it might seem very chaotic, only local people go there, but I can assure you that the food is amazing...and the prices are even better!

Livorno's lungomare

Livorno's lungomare

Day 14: Our final stop was Pisa... We didn't have a lot of time because we stopped on the way to the airport...Pisa is not very big but there are quite some things to do and to see! Make sure not miss the Leaning Tower and the Piazza dei Miracoli!

Pisa's  leaning tower

Pisa's  leaning tower

Our holiday in Tuscany was more than amazing! In my opinion, Tuscany is one of the most beautiful places in the world and if you have the chance to visit it, I promise you - there will be no regrets! 

For other helpful tips and info, check my blog post: How To Make Your Italian Holiday The Trip of Your Life?

I hope you find this blog post useful and please if you have any questions, don't hesitate to ask me! 

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