Tuscany Italy – A Wonderful One-day Road Trip through the Countryside

Italy is a beauty. This Mediterranean pearl in the shape of a boot and surrounded by aquamarine water, is packed with lovely travel destinations. Quite a large number of them make a perfect combination for a lovely road trip through the Italian countryside.

Tuscany in Italy is the place to be when it comes to good food, abundant amounts of wine, great sceneries and small medieval towns to fall in love with. All you need for a road trip.

The climate in Tuscany is pleasant almost the whole year. So, there is no excuse for not doing a road trip.

You will love Tuscany.

This travel guide brings you a nice scenic one-day route in Tuscany, Italy. One that will lead you through two beautiful medieval villages and two marvelous Italian cities through little roads in the countryside.

The beautiful countryside of Tuscany Italy. The beautiful countryside of Tuscany Italy.


A road trip itinerary through Tuscany, Italy


With earthy colored buildings and ancient city walls, an old medieval tower and an old castle. Montecatini Alto is a small, cozy and very picturesque town in Tuscany Italy.

Montecatini is located in the province of Pistoia in Tuscany, Italy. Situated right in the middle of the beautiful valley of the river De Nievole.

When you find yourself to be in the area, keep in mind that Montecatini Terme is one of the most important thermal bathing places in the all of Europe. It’s quite worth it to pay a visit to them.

Montecatini Alto, which is located just next to Montecatini Terme is the old part of the city.

History of Montecatini Terme

In the 14th century, a great discovery took place in Montecatini. Thermal waters were found in the area with therapeutical and medical benefits. The thermal water was also believed to have a positive effect on the looks of people who used the baths.

The revelation had quite a monumental value and would have a big impact on the growth of Montecatini Terme.

The first spa baths in Montecatini Terme were constructed in 1530. These thermal baths made the spa grow in popularity with the Italian people. Even the Medici family incorporated them into their Grand Dukedom.

A small village in Tuscany Italy. A small village in Tuscany Italy.

Things to do in Montecatini

The area around Montecatini is a true delight to explore. Either Montecatini Alto and Montecatini Terme are must-visit places on your road trip in Tuscany.

1. Montecatini Alto

The picturesque village of Montecatini Alto is located right next to Montecatini Terme in Tuscany, Italy. 

You’ll get magnificent views of vineyards and charming little streets to enjoy when you visit Montecatini Alto.

This small village once counted about 5400 inhabitants in old medieval times. Nowadays, only a few people still live in the town.

In the winter months, the town of Montecatini Alto looks almost deserted. This is quite a contrast compared to the summer when many tourists wander the streets of the old town.

You can either drive up to the town or you can take the funicular up.

2. Thermal Spa Baths of Montecatini Terme

The beautiful thermal baths will offer you a chance to enjoy the waters the Romans once loved. There are eleven thermal baths in Montecatini Terme. One of the biggest spas in the area is the Terme di Montecatini Spa.

One of the biggest spas in the area is the Terme di Montecatini Spa.

You can choose to tour the grounds, sample the famous waters and see the well-tended gardens for a small fee. You can also go for a nice swim in the baths or go for a nice spa treatment.

Tuscany Italy Countryside villageThe Tuscany countryside in a perspective from a small local village.

San Gimignano

In short, San Gimignano in Tuscany is a charming old village with fortified walls and a few medieval towers. A town you shouldn’t skip. 

Colours of pastel, adventurous small roads and the smell of delicious pizza are to be found in San Gimignano.

The village of San Gimignano is noted down as one of the more popular travel destinations in Tuscany, Italy.

San Gimignano in Tuscany Italy. San Gimignano in Tuscany Italy.

History of San Gimignano

In medieval history, the wealthiest and most powerful families from San Gimignano competed against each other by building the highest tower of the town. 

As a result, San Gimignano once had 72 of those massive towers, some were as tall as 50 meters.

Nowadays, only seven of the remaining towers stretch up under the Tuscan sun around Piazza del Duomo. You have the option to climb one of remaining towers on your visit to San Gimignano. The view from up there is truly astonishing.

All the rest of the old towers were destroyed over time by fires, assaults, and antiquity.

A medieval tower in San Gimignano on a road trip through Tuscany Italy A medieval tower in San Gimignano on a road trip through Tuscany Italy

Things to do in San Gimignano

Discover the village of San Gimignano and enjoy delicious Italian ‘gelato’ ice-cream in one of the small shops. The tiny streets in the village are a joy to explore.

1. Explore the fortress of La Rocca di Montestaffoli

In San Gimignano, you can walk up the hill to the ruins of a 14th-century fortress. The view from this fortress will give you a nice view over the whole village.

Lovely olive groves in the fortress provide shade from the sun and a great place to enjoy some nice snacks while enjoying the views of the Tuscan hills and the towers rising from the town center of San Gimignano.

Some old ruins in San Gimignano in Tuscany Italy. Some old ruins in San Gimignano in Tuscany Italy.


2. Climb the Tallest tower in San Gimignano

Torre Gross, the tallest tower of San Gimignano dates back to 1298. The tower is 54 meters (177 feet) tall and it’s the only tower in the village that is open to the public.

You can climb to the top of Torre Gross for great views over the Tuscany countryside.

3. Enjoy a delicious gelato

The world-famous Gelateria di Piazza is located right in the center of San Gimignano.

The gelato shop offers a nice variety of ice cream with many different creative flavors.

You’ll easily recognize the place by looking for a long a waiting line onto the street.

A crowdy street in San Gimignano on a road trip through Tuscany Italy A crowdy street in San Gimignano on a road trip through Tuscany Italy


Via Francigena is a historical pilgrim route that stretches out far from Western Europe to Rome. The trail itself passes many small towns and larger cities.

Monteriggioni used to be of those small pilgrim towns.

History of Monteriggioni

Monteriggioni is another fortified medieval town that sprouted under the rule of the old kingdom of Siena.

The settlement has fortified medieval city walls, drawbridges, a castle moat and massive gates. Exactly how a Tuscan medieval settlement should look.

The area around Monteriggioni is literally breathtaking. You will love the view on colorful vineyards, many olive trees and beautiful Mediterranian hills that surround the old village.

Many old battles were fought for Monteriggioni in medieval times. The strategic location of the settlement had a lot of economic value in old Tuscany, Italy. 

The town of Monteriggioni is also famous because Templars used to reside in the village.

But, once the Florentines captured the town it started to decay. Until it was rebuilt in the 20th century under command of Mussolini.

Things to do in Monteriggioni

Monteriggioni is located right in the heart of Tuscany and is surrounded by beautiful hills decorated with vineyards and fields full of grain and olive trees.

It’s quite pleasing to walk around in the medieval village of Monteriggioni.

One of the best things to do in the village is to walk along its fortified walls. You will have a great view here over the stunning colorful Tuscany countryside.

The beautiful countryside of Tuscany, Italy. The beautiful countryside of Tuscany, Italy.
A curving street in a small village of Tuscany Italy. A curving street in a small village of Tuscany Italy.


There are quite a few medieval cities in Tuscany. But, I found Siena to be the most beautiful one.

With small cobblestone streets, earthy colored buildings, a clear blue sky and a lot of romance and wonderful coziness, Siena makes a perfect travel destination in Tuscany to hang around for a couple of days.

I personally would choose Siena over Florence because it’s smaller and prettier.

Duomo di Siena of Cattedrale di Santa Maria Assunta in Siena on a road trip through Tuscany Italy Duomo di Siena of Cattedrale di Santa Maria Assunta in Siena on a road trip through Tuscany Italy

History of Siena

The Romans established the defensive military outpost of Siena In 30AD, which later blossomed into a busy trading post.

Whilst time flew by and Siena grew out to become a majestic medieval city, territories expanded and rivals sprouted.

So it happened that the empire of Florence eventually conquered the empire of Siena after many battles that were fought between the 13th and 15th century.

Siena was then added to the rival territory of Florence until the republic Italy was formed.

When this happened, Siena became part of the region of Tuscany.

The beauty and prosperity of the city today can be thanked to its great artistic heritage.

Heads of stone on a building - road trip through Tuscany Italy Heads of stone on a building – road trip through Tuscany Italy

Things to do in Siena

Many beautiful piazza’s and mighty churches decorate the city area. And, delicious food is served in the many small restaurants that are widespread in the city

1. Piazza del Campo

The famous Piazza del Campo is located right in the warm heart of Siena. It features a number of iconic monuments, including the mighty Torre del Mangia and the Fonte de Gaia.

2. Climb the Torre del Mangia

Rising high above the Piazza del Campo, the Torre del Mangia stands at 102 meters high.

The tower dates back to the 14th century and one was the second tallest building in medieval Italy. It was built to be the same height as the Siena cathedral in order to reflect the equal power of the church and the state.

The climb to the top of the Torre del Mangia sure is worth the experience of the unbeatable views of the city and its surrounding countryside.

You can’t miss this one when you’re in Siena.

Torre del Mangia in Siena on a road trip through Tuscany Italy Torre del Mangia in Siena on a road trip through Tuscany Italy

3. Duomo di Siena of Cattedrale di Santa Maria Assunta

There are many majestic cathedrals to be found in Tuscany, Italy. But none of them will be as great as the Siena Cathedral, which is one of Italy’s most noble Romanesque and Gothic Cathedrals.

The Duomo di Siena is of the city’s most valuable art treasures. Either the inside as the outside of it is amazing.

Explore the cathedral and take a close look at all the details of this majestic structure.

See more travel guides and articles about Italy.

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Roadtrip in Tuscany Italy
Roadtrip in Tuscany Italy

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