If you’re looking to take a road trip in Italy, one of the most icon regions to do it is Tuscany. The 10-day itinerary that I’m going to share in this article will take you through some of the top sights as well as less touristy spots.

Tuscany-pinterest

My knowledge of Tuscany has always been limited to Florence, hence a visit to this fantastic corner of Italy was long overdue. I must say that it’s been quite a challenge to draft an itinerary due to the enormous amount of things to see and do here, so I decided to focus on central and eastern Tuscany and leave the coast to another trip (Isola d’Elba alone would probably require a week!).

Tuscany itinerary overview

Day 1: Lucca

Day 2: Volterra, San Gimignano

Day 3: Monteriggioni, Chianti, Siena

Day 4: Siena

Day 5: Crete Senesi, Montalcino, San Quirico d’Orcia

Days 6-7: Val D’Orcia

Day 8: Montepulciano, Cortona

Day 9: Valtiberina (Monterchi, Anghiari, Sansepolcro)

Day 10: Arezzo and back home

Day 1: Lucca

Tuscany-LuccaThis Tuscany road trip starts in Lucca, a pretty town often overlooked in favor of nearby Pisa’s Leaning Tower. Hometown of opera composer Giacomo Puccini, Lucca is a truly fascinating place with a wealth of impressive architecture, fine art and cheerful cafes.

  • Don’t miss: the unique Piazza dell’Anfiteatro, the imposing Cathedral of S. Martino, the Guinigi Tower with its unusual rooftop garden and a walk or bike ride along the ancient walls
  • Stay at: Affittacamere Il Cactus, a cozy guest house close to the town centre, with lots of parking space and free bicycles for touring around
  • Eat: try the local delicacies offered by La Bottega di Anna e Leo, a small trattoria right in the historic centre

Check out my article on what to do in Lucca for more information.

Day 2: Volterra and San Gimignano

 

Tuscany-VolterraAbout 1.5 hour drive from Lucca, Volterra is a pretty hill town founded by the Etruscans more than three thousand years ago. From Piazza dei Priori, one of Italy’s most beautiful medieval squares, it’s a delightful maze of narrow streets and alleys lined with ancient buildings and small craft shops selling alabaster, the stone Volterra is famous for.

  • Don’t miss: Piazza dei Priori (where that Twilight scene was filmed…), the Etruscan Museum and Via Porta all’Arco (also known as “Artisan Lane”) with lots of artisan shops and workshops

Tuscany-San GimignanoI then headed east towards San Gimignano (about 45 minutes away), which is often referred to as the “Italian Manhattan” due to the amazing medieval towers that punctuate the sky of this atmospheric corner of Tuscany. This lovely town brims with splendid palaces and churches and although it’s way more touristy and crowded than Volterra, I really enjoyed exploring its streets. It’s no surprise that it’s been declared a Unesco World Heritage site!

  • Don’t miss: the Basilica of Santa Maria Assunta, with an impressive series of frescoes by illustrious painters of the Sienese school, and a walk up to Torre Grossa, the tallest tower in town, to enjoy the fantastic views
  • Stay at: Antico Casolare, an excellent b&b just outside the city walls, with spacious rooms, parking space and an astonishing view of San Gimignano from the garden
  • Eat: lunch at Sosta sulla Francigena with its fantastic terrace overlooking vineyards and green fields, taste some of the best gelato in the world at Gelateria Dondoli, and have a glass of Vernaccia, the local white wine

Day 3: Monteriggioni, Chianti, Siena

 

Tuscany-MonteriggioniMy first stop on the way to Chianti was Monteriggioni, a sleepy hilltop village surrounded by thick stone walls. This place is really tiny, with lots of cute craft shops and cafes. Avoid peak times when the village is packed with group tours; I arrived around 9am and had the place all to myself – although it must be lovely also at night with those cozy bars and restaurants all lit up!

From Monteriggioni it’s a 20-minute drive to reach Castellina in Chianti, the gateway to my tour of the wine region of Chianti. Castellina is a lovely hilltop village with a fascinating vaulted passageway (via delle Volte) that sneaks through the medieval town walls.

I spent the rest of the day driving through rolling hills and suggestive grapevine fields, stopping by some of the most beautiful villages of this area: Montefioralle, one of the quietest and most authentic hamlets around Chianti as well as a photographer’s paradise, Greve in Chianti, the region’s main town, Radda in Chianti with its picturesque Palazzo del Podestà, and the market town of Gaiole in Chianti.

Tuscany-ChiantiAfter many wine purchases and one of the longest photo sessions ever (I simply couldn’t stop taking pictures!), I spent the night in Siena in order to have a full-day exploration the following day.

  • Don’t miss: forget maps and guidebooks, enjoy the food and wine and admire the stunning Tuscan countryside
  • Stay at: Borgo Grondaie, a gorgeous hotel in a very handy location for those traveling by car, near the station and with lost of parking space (the walk to the town centre is around 30 minutes, though)
  • Eat: Antica Macelleria Falorni, a traditional butcher’s shop in Greve, selling excellent food and wine that you can consume at one of their tables or on a picnic (they even have a fantastic cheese cellar!)

Day 4: Siena

 

Tuscany-SienaOne of the top sights in Tuscany, Siena is a charming, elegant town filled with superb examples of medieval architecture and rich artistic treasures. One of the most fascinating aspects of Siena is that it is divided into 17 neighborhoods called contrade, each with its own constitution, traditions and history – and locals have a really strong sense of belonging to their own contrada!

  • Don’t miss: the astonishing Piazza del Campo, the Civic Museum with the fantastic frescos showing The Allegory of Good and Bad Government, the Torre del Mangia (500 steps!), the Cathedral of Santa Maria Assunta and the Complex of Santa Maria della Scala (check out special tickets and passes here)
  • Eat: try the tasty panini of Gino Cacino, buy some sweet treats at Antica Drogheria Manganelli and have dinner at Osteria La Chiacchiera

Day 5: Crete Senesi, San Quirico d’Orcia

 

Tuscany-Crete-SenesiTime to venture through what I reckon to be the prettiest drive in Tuscany, Crete Senesi. The name of this area derives from the distinctive clayish colouration of the soil which gives the landscape a lunar appearance. It’s a fantastic roller-coaster series of hills covered in wheat fields, cypress-lined roads and olive trees. I finished the day at San Quirico d’Orcia, the town that I used as a base to explore Val d’Orcia in the following two days.

  • Don’t miss: the pretty hamlet of Asciano, the stunning Abbey of Monte Oliveto Maggiore with the cute little village of Chiusure and the delightful historic centre of Buonconvento
  • Stay at: Agriturismo La Buca di Bellugi, a charming farmhouse immersed in the Tuscan countryside
  • Eat: lunch at Locanda Paradiso in Chiusure and dinner at Al Vecchio Forno in San Quirico

Days 6-7: Val d’Orcia

 

Tuscany-Vitaleta-ChapelVal d’Orcia is a land rich in history and scenic corners, home to some of the prettiest villages in Tuscany, with rolling hills in all shades of green and yellow punctuated by rows of vineyards, cypresses and stone farmhouses.

  • Don’t miss: the dreamy Vitaleta Chapel in San Quirico, the ancient Roman baths of Bagno Vignoni, the fortified citadel of Castiglione d’Orcia, the beautiful Pienza, that was regarded as a perfect example of urban planning back in the Renaissance, Montichiello, a quaint hamlet famous for the theatre pieces that locals write and stage each summer in the main piazza, and the lovely little wine village of Montalcino
  • Eat: have some excellent local food at La Cisterna nel Borgo in Castiglione d’Orcia and Sette di Vino in Pienza, and don’t forget to indulge in the tasty pecorino cheese Pienza is famous for!

Day 8: Montepulciano, Cortona

 

Tuscany-MontepulcianoA 30-minute drive took me from San Quirico to Montepulciano, another beautiful Tuscan medieval gem. Montepulciano is famous for its elegant palaces, ancient churches and excellent wine. I covered the main sights in a couple of hours and then I drove eastwards to Cortona. I spent the rest of the day there, venturing along its tiny alleys fabulously lost in time.

  • Don’t miss: Piazza Grande and the Church of S. Agostino in Montepulciano, the Basilica of S. Margherita and the Eremo Le Celle in Cortona
  • Stay at: Locanda Pane e Vino, a lovely b&b in the heart of Cortona, with stylish rooms and a cute little garden
  • Eat: savour the genuine cuisine of Trattoria Dardano and the delicious snacks and craft beers of Birrificio Cortonese, both in Cortona

Day 9: Valtiberina

 

Tuscany-MonterchiFrom Cortona I drove through winding roads into to the heart of Valtiberina, a beautiful yet mysterious corner of Tuscany at the border with Umbria. Valtiberina is still quite unknown to tourists, despite being the birthplace of illustrious artists such as Michelangelo and Piero della Francesca, and boasting fascinating medieval hamlets.

  • Don’t miss: Monterchi, with its unique Scale Museum and the extraordinary display of Piero della Francesca’s “Madonna del Parto”, the magnificent old town of Anghiari, with its stone houses and artisan workshops, and the village of Sansepolcro, Piero’s hometown, with a Civic Museum that hosts some oh hist masterpieces
  • Stay at: B&B Dolce Rosa, a newly opened guesthouse just a stone’s throw from Sansepolcro’s cathedral
  • Eat: have lunch at Al Cantuccio in Anghiari, while in Sansepolcro you shouldn’t miss the sweet delicacies of Pasticceria Chieli and a dinner at Enoteca Guidi, a favourite with both locals and travelers

Day 10: Arezzo and back home

 

Tuscany-ArezzoAbout 40 minutes from Sansepolcro, Arezzo is the capital city of eastern Tuscany. Although it gets far less attention than Florence and Siena, this beautiful town has plenty to offer, with a rich art and architecture

  • Don’t miss: the impressive Piazza Grande and the Bacci Chapel in the Basilica of S. Francesco with the fresco cycle “Legend of the True Cross” by Piero della Francesca.
  • Eat: try the gourmet sandwiches of La Bottega di Gnicche, where you can also stock up on some excellent food souvenirs to bring home with you

From Arezzo I took the fast road back home, but if you have more time then you could add a couple of days in Florence (about an hour away).

USEFUL TIPS

  • Tuscany is a foodies’s paradise, especially if you like strong flavors; don’t leave without trying crostini (crunchy slices of bread served with liver pate), pecorino cheese, pici pasta, ribollita soup, and some world-renowned Chianina beef meat
  • This part of Italy is filled with tourists practically all year around but I recommend taking this trip either in April-June, when there are mild temperatures and beautiful blooming fields, or in September/October when the calendar is filled with food festivals and grape harvest events

 

Until next time,

Tags: , , , , , , , ,

4 Comments

Danielle 22 January 2018 at 21:22

Wow! This sounds like an amazing trip! Thank you for the tips!

    admin 22 January 2018 at 21:49

    Amazing trip indeed! Hope this will be useful for a feature trip 😉

PossesstheWorld 23 January 2018 at 06:08

We stayed in Tuscany for the month of March 2017, in a small town Lucignano and visited many of these towns for market days, it is absolutely magnificent to see the spring foliage appear and to share the towns with mostly Italian people. Great post, it brought back many memories

    admin 23 January 2018 at 08:14

    That sounds fantastic! I missed Lucignano, I’ll write it down for my next trip 🙂

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Ciao! I’m Val

Ciao! I’m Val

Ciao! I'm Valentina, an Italian blogger with a huge passion for my country, its culture and traditions. My Italian Diaries is the online space where I share my expert knowledge of itineraries, activities and off-the-beaten path places to help you experience the best of Italy like a local.

READ MY STORY

Signing

CONNECT WITH ME


Shabby-Sheep-Design-discount
 

TOURS IN ROME PROMO CODE: MYITALIANDIARIES5

Subscribe

My Italian Diaries Newsletter

* indicates required

RECENTPOPULARTAG