Winter in Tuscany: 3 Italian Hill Towns Worth Seeing

Winter in Tuscany: 3 Italian Hill Towns Worth Seeing

This past winter we spent some time in Tuscany during our Italy road trip. While we already wrote a post on our all-time favourite town, Montepulciano, Italy, however there are hundreds of beautiful hill towns to explore! Winter was a great time to visit because it wasn't as crowded as in the summer. It could be chilly at times, but the sun still shone brightly most days.

So whether you are there to explore, relax, or visit a Tuscan winery, here are three Tuscan hill towns we thought deserved a mention.

Montefollonico, Italy: Tiny But Charming and Delicious

Montefollonico is a tiny walled town just a stone's throw away from Montepulciano. You can see it in the stunning panoramic views from Montepulciano, and from Montefollonico you have views of Montepulciano as well! Since this town is very tiny, you won't find much happening here but it is a very charming town to explore.  However, it might surprise you to learn that this tiny Tuscan town is home to a Michelin star restaurant, La Chiusa.

If you want a more quiet, laid back place to use as a home-base for your Tuscany vacation, look no further than Montefollonico. There are several vacation rentals and Airbnbs available in town, and you are just a very short drive away from many famous Tuscan towns.

 Part of the fortifications of Montefollonico

Part of the fortifications of Montefollonico

 Just one of the many interesting doorways in Montefollonico

Just one of the many interesting doorways in Montefollonico

 Typical street in Montefollonico

Typical street in Montefollonico

San Gimignano, Italy: The Town of Fine Towers

Try this tour - Taste of Chianti: Tuscan Cheese, Wine and Lunch From Florence

Perhaps the most famous of the three Tuscan hill towns mentioned in this post, San Gimignano is much bigger than Montefollonico and Montepulciano. It is home to 13 towers that are still standing of an original 72 dating back to the 14th century. In those times, all the wealthy families built towers to show their economical power.

Unfortunately even in the winter we felt the consequences of the fame of this town. It was much more crowded than anywhere else we had visited in Tuscany. However, regardless of its popularity, you can still find quaint back streets and alleys that aren't flooded with tourists.

 View from our hotel room balcony in San Gimignano

View from our hotel room balcony in San Gimignano

We chose to stay in Albergo La Cisterna, which is conveniently located right in the main piazza in town, which was great for sightseeing. However due to the crowds gathering outside we found it a little noisier than we'd like. Their onsite restaurant was also very mediocre. The views from our balcony made up for the noise though.

 Evening view from our hotel balcony in San Gimignano

Evening view from our hotel balcony in San Gimignano

 Piazza Della Cisterna in San Gimignano

Piazza Della Cisterna in San Gimignano

 Piazza Della Cisterna in San Gimignano

Piazza Della Cisterna in San Gimignano

 View looking in from the city walls in San Gimignano

View looking in from the city walls in San Gimignano

 View looking out from the city walls in San Gimignano

View looking out from the city walls in San Gimignano

 Typical street in San gimignano...look towards one of the gates

Typical street in San gimignano...look towards one of the gates

Montalcino, Italy: Best Place to Wine and Dine

More famous for its wine than for the town itself, Montalcino is still a very intriguing place to visit with remarkable views, churches, and fortress. It is also home to the restaurant where we had the best meal of our lives!

The day we visited, there was an extremely cold wind, so it was difficult to enjoy exploring the town, but the next morning was nice and sunny and while still cold, much more pleasant to walk around.

While strolling around the cobblestone streets, it is very apparent this is a wine town, with several wine shops (enoteca) on every corner. Make sure to stop in at least one to sample their famous (and expensive!) Brunello di Montalcino.

 View from our hotel room window in Montalcino

View from our hotel room window in Montalcino

 Our hotel, Albergo Il Giglio in Montalcino

Our hotel, Albergo Il Giglio in Montalcino

We stayed at Albergo il Giglio in Montalcino, which boasts impressive views of the valley below and has its own Michelin star restaurant. We didn't dine in their restaurant due to the immense amount of pork on the menu that evening, but it has very good reviews.

 Piazza del Popolo in Montalcino

Piazza del Popolo in Montalcino

 View from the fortress at the top of Montalcino

View from the fortress at the top of Montalcino

 Delisa trying to stay warm in Montalcino despite the icy winds!

Delisa trying to stay warm in Montalcino despite the icy winds!

 A side street in Montalcino in the warm morning sunshine

A side street in Montalcino in the warm morning sunshine

 The fortress at the top of Montalcino

The fortress at the top of Montalcino

The highlight of our visit to Montalcino was our dinner at Drogheria Franci, which is the best meal we've ever had. We wish we had taken photos of every dish, but always feel embarrassed about taking pictures of the food in restaurants. Plus we usually get excited and dive in immediately and forget to take a photo first. 

 Fresh White Truffle Pasta from Drogheria Franci

Fresh White Truffle Pasta from Drogheria Franci

We started with a delicious cheese plate accompanied by a glass of the famous Brunello di Montalcino. For the main course, Marcin had a sea bass dish, and I had a pumpkin and amaretti risotto, both of which were delectable. But the true star of the meal was the fresh white truffle pasta.

After we ate our main course, our server brought out the freshly made pasta simply dressed with butter, and a fresh white truffle. He weighed the truffle on a scale first, then delicately shaved it atop each of our pasta dishes, then weighed the truffle again since they charge by the gram. 

Try this tour - Montalcino Truffle Hunting

Even though our bank account suffered a little from this meal, it was worth every penny and we still drool every time we think about that truffle pasta. The tiramisu we had for dessert was also delicious, but just could not compare with the truffle pasta. We would definitely eat there again next time we are in Montalcino.


 

While there are many, many more towns in Tuscany we need to explore, these were the top three we wanted to share from our latest trip. 

Try this tour - Tuscany 1-Day Sightseeing Tour

Have you been to Tuscany? What was your favourite hill town? Do you have an unforgettable meal you'd like to share? Let us know in the comments!

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 Winter in Tuscany: 3 Italian Hill Towns Worth Seeing
 Winter in Tuscany: 3 Italian Hill Towns Worth Seeing