The Best Places to Visit in Tuscany, Italy for a Memorable Roadtrip

Best Places to Visit in Tuscany

Choosing the ultimate Best Places to Visit in Tuscany can be a difficult task, with so many wonderful little villages to explore during your road trip.

Who hasn’t dreamed of driving an adorable Fiat 500 through the lush, green, rolling hills of the Tuscan countryside, passing by sprawling vineyards and Tuscan mansions, as iconic Cypress trees dot the landscape?

Best Places to Visit in Tuscany

There’s a reason Tuscany is a location in so many romantic movies – it really is a stunningly beautiful area of Italy, full of charming scenery, quaint little walled towns to explore, and elegant vineyards where you can enjoy sampling some of the world’s best wines.

If you’re putting together your own Italian itinerary, this guide will help you discover the absolute best places to visit in Tuscany!

Quick Links to Best Places to Visit in Tuscany:


This walled town in Tuscany is known for its perfectly rounded walls sitting high on a hilltop. Monteriggioni’s fortified walls are still intact and walkable, and its tightly-woven cobblestone streets are a joy to explore. It also features 2 gates, the Franca or Romea Gate facing Rome, and the Florentine Gate, which heads towards Florence. Monteriggioni’s castle walls provide panoramic views of the surrounding Chianti region and Val d’Elsa. This is a great destination to stop at during your Tuscan road trip! Learn more on this guide to Monteriggioni.

est Places to Visit in Tuscany

Best Things to Do in Monteriggioni:

  • Attend the The Medieval Festival of Monteriggioni, should you arrive in July
  • Go for a walk along the walkways on the walls, as if you were soldiers on patrol
  • Visit the Church of St. Mary of the Assumption, built in 1213
  • Visit the elegant Church of Santa Maria in Castello
  • Try on armors at the ‘Monteriggioni in Arme’ Museum

Best Places to Visit in Tuscany

San Gimignano

San Gimignano is sometimes known as Italy’s “Medieval Manhattan”. This name makes sense, as San Gimignano has a skyline of fourteen stone towers soaring dramatically above the Tuscan countryside. Originally there were actually 72 towers, each built competitively by San Gimignano’s patriarch families to display of their wealth. As beautiful as these towers are, there is plenty more to see and do in San Gimignano!

Best Places to Visit in Tuscany

Best Things to Do in San Gimignano:

  • Explore La Rocca di Montestaffoli, the remains of a 14th century fortress above the town
  • Climb to the top of the Torre Gross, the only tower open to the public and San Gimignano‘s tallest tower (at 54 meters / 177 feet)
  • Drink Vernaccia di San Gimignano wine (so famous it was even mentioned in Dante’s Inferno)
  • Enjoy award-winning, uniquely-flavoured gelato at the world-famous Gelateria Dondoli, located right in the center of Piazza della Cisterna. So easy to find – just look for the large lineup!
  • Wander the streets and ogle the beautiful Italian designer goods
Best Places to Visit in Tuscany
Line up for gelato at the Gelateria Dondoli (spoiler: it’s worth waiting for!)

Best Places to Visit in Tuscany


Siena is a well-known historic city, famous for its Palio Horse Race that happens twice a year. It is picturesque and charming, with narrow streets flanked by stunning brick buildings. Listed as a world heritage site by UNESCO, there is certainly a lot to see and do in Siena. Here are a handful of my recommendations:

Best Places to Visit in Tuscany

Best Things to Do in Siena:

  • Visit Piazza del Campo, one of the biggest medieval squares in the world
  • Enjoy the Palio Horse Race, if you can plan your visit on July 2 or August 16
  • Climb the 400 steps up the Torre del Mangia for a spectacular sweeping view
  • Marvel at the black and white masterpiece of the Cathedral
  • Visit the Complex of Santa Maria della Scala, which was once an important civic hospital dedicated to caring for abandoned children, the sick, and the poor
  • Sample traditional food and wine in Siena. Food: wild boar, pappardelle pasta, local sausages, ribollita soup, and for wine: Chianti, Brunello di Montalcino, Montepulciano and Vernaccia di San Gimignano


Pienza, a UNESCO heritage site, is incredibly charming, chalk-full of ivy-draped walls and perfectly potted plants framing the cutest of doorways.

On the drive into Pienza, you’ll be so engrossed with the landscape of rolling hills dotted with rows of cypress trees of the Val D’Orcia that you might be tempted to pass through Pienza without stopping, but this charming Tuscan village is completely worth a visit – especially for those of you that are cheese-lovers! Pienza is well-known for its delicious Pecorino cheese, which is a sheep’s milk cheese full of tasty varieties. Some shops even let you pop in and sample varieties before you purchase!

Best Places to Visit in Tuscany

Pienza was designed to be a Utopia of sorts. During his pontificate, Enea Silvio Piccolomini (more widely known as Pope Pius II) took charge of rebuilding Pienza according to his ideals of the “perfect city” based on the humanist values of the time, and you can feel a beautiful synergy in his design of this village.

Best Places to Visit in Tuscany

Best Things to Do in Pienza:

  • Sample Pecorino cheese at one of the many local artisan cheese shops in town
  • Pair it with some local Tuscan honey from a local specialty shop
  • Visit a cheese farm to witness Pienza cheese-making
  • Explore the ancient walls of Pienza, which have been declared a World Heritage Site
  • Visit Palazzo Piccolomini, one of the main architectural feats in Pienza
  • Visit the Cathedral of Santa Maria Assunta, a beautiful geometric church built in 1459 that has remained virtually the same since, due to changes being forbidden

Best Places to Visit in Tuscany


Montalcino is a quiet and beautiful Tuscan village that has undergone few changes since medieval times, where it was once a strategic point along the road to Rome. This village offers stunning, sweeping views of the Asso, Ombrone, and Orcia valleys.

It is a well-known and well-loved Tuscan village, known for its production of Brunello (one of Italy’s finest and prestigious of red wines), which is made exclusively from Sangiovese grapes grown in Montalcino.

An amazing pool amidst the vineyards at Canalicchio di Sopra
An amazing pool amidst the vineyards at Canalicchio di Sopra

Best Things to Do in Montalcino:

  • Visit the Abbey of Sant’Antimo and Fortezza di Montalcino
  • Discover history and wine at Palazzo Pieri
  • Visit the 9th century Bibbiano Castle
  • Ogle the artwork at Museum Civico e Diocesano
  • Visit Canalicchio di Sopra for an incredible Brunello wine-tasting experience in their vineyard (they have incredible accomodation options here as well)
Best Places to Visit in Tuscany
Wine tasting (Brunello) at Canalicchio di Sopra


This town south of Rome is known for its tuff stone, which is hardened volcanic magma and unique to this area of Italy. Pitigliano is positioned on a steep tuff bluff, and your first view of it will take your breath away.

The village is referred to as “Little Jerusalem”, not only because it looks ancient and bears a resemblance to Jerusalem, but also due to the long presence of Jewish community in the village.

Best Places to Visit in Tuscany

Best Things to Do in Pitigliano:

  • Visit the remains of the Etruscan city wall
  • Meander through Orsini-Park, created at the end of the 16th century and see statues and stone seats carved from the tuff
  • Wander the Etruscan Paths with walls more than 10 metres high, dug into the rock by the Etruscans. They wind down to the river valleys below
  • Visit the two impressive museums (archeology and art)
  • Visit the tiny, compact theatre that comes to life with music and theatre


Lucca is one of the most-loved cities in all of Tuscany and cannot be missed on any itinerary of this region! You can visit Lucca in a day, but if you want to really all it has to offer, consider staying overnight for a couple of nights and use it as a launching off place to discover the rest of Norther Tuscany.
This city is located at the foot of the Apuan Alps and isn’t a hilltop village, like the majority of Tuscany’s towns and cities. This can be a nice reprieve from all of the hill-climbing you will be doing as you explore Tuscany!

Best Places to Visit in Tuscany

Best Things to Do in Lucca:

  • Find a tower to climb – there’s plenty of options! Lucca’s skyline is full of historic towers offering stunning viewpoints (and if you only have time for one, choose Guinigi Tower)
  • Wander the streets – Lucca is very pedestrian-friendly, and this is the best way to get a feel for its charms
  • Visit the Chiesa di San Michele in Foro, one of Lucca’s most grande churches
  • Hang out in the Piazza dell Anfiteatro, which was once a was once a Roman Amphitheatre
  • Take a walk on the historic city walls
  • Visit the Basilica di San Michele in Foro, a stunning church in the centre of Lucca
  • Visit the expansive Communal Botanical Gardens of Lucca for a nature break

There’s absolutely no doubt about it that your road trip to Tuscany will be amazing regardless of where you do and do not decide to stop. There is so much to see and do, from lush rolling landscapes to ogle, elegant vineyards to visit and delicious wines to taste, traditional foods to try, and amazing architecture to find. There is so much history in this incredible part of Italy, full of medieval tales and stories, You can decide to spend as much or as little time in each of these villages and cities as you choose. Perhaps you just want to quickly wander around the walled cities and look up to the towers. Or perhaps you want your entire trip to be about wine and discovering the varietals in each area of Tuscany. Or maybe you’re hoping to make your own self-led food tour, or shopping trip. Any of these purposes make a fantastic itinerary through Tuscany.

We just wanted to soak it all in and let all of our senses be overwhelmed by this region of Italy, which seems to jump right out at your from a fairytale storybook. Enjoy your trip (and all the delicious wine and cheese you are about to savor!)

Map of Tuscany:

Here is a map showing where each of these areas are located, so you can plan your perfect road trip through Tuscany!

Car Rental Recommendation for your Tuscany Roadtrip:

I booked through Centauro Rent-a-Car, picking up the vehicle at the Rome airport and dropping it off at the Pisa airport. I highly recommend this company – their vehicles were beautiful, prices very affordable and staff friendly and adequate. The vehicle was also so extremely fuel-efficient – we spent such a low amount of money on petrol!

Disclaimer: The vehicle rental portion of this getaway was kindly sponsored by Centauro Rent-a-Car, and our wine tour and villa accommodation was kindly sponsored by Canalicchio di Sopra Wine Relais. However, as always, all thoughts and opinions are entirely my own. I will continue to promote only properties, destinations, products and services that I truly believe in 100%, and would wholeheartedly recommend to others. 


Best Places to Visit in Tuscany

Best Places to Visit in Tuscany

Best Places to Visit in Tuscany

Best Places to Visit in Tuscany

Best Places to Visit in Tuscany

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Questions or questions about Tuscany or any of the villages mentioned in this blog post? I’d love to hear from you – just leave me a comment below!


The Best Places to Visit in Tuscany, Italy for a Memorable Roadtrip

I’m Jenn, a photographer, travel writer, and content creator based out of the beautiful Canadian Rockies. I’m glad you’re here – now let’s explore!

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