5 Of My Favorite Hilltop Towns of Tuscany

There's something romantic and alluring about Tuscany, Italy. Maybe it's the rolling hills, breathtaking sunsets, vineyards, or the unique and beautiful hilltop towns. With their fortified walls and cobblestone alleys, these towns make you feel like you have taken a step back in time.

Here are 5 of my favorite hilltop towns in Tuscany.

1. Siena

During my initial visit to Italy, I first encountered the region of Tuscany through the town of Siena. It continues to be one of my favorite places. Although it's a sizable city and often attracts many tourists, you shouldn't let that stop you from adding it to your itinerary.

Siena is about 35 miles from Florence; many people visit this medieval town. If your itinerary permits the extra time, you will not regret a few days, and it makes a great home base while exploring Tuscany.

On your visit to Siena, stroll down the narrow alleys and enjoy the local community in the big central piazza of Il Campo. There are 17 unique and colorful districts surrounding the piazza, and not far from there is the very impressive Duomo. Siena is also the location of the famous horse race, the Palio, in which the competing districts race twice yearly in the Piazza del Campo.

2. San Gimignano

San Gimignano is a popular hilltop town known for its tall medieval towers, and it's a gem. Over 70 towers stood over the area as symbols of wealth and power. Today, there are 14 left standing. Don't let that number detour you from visiting, as there is more than the reigning towers to enjoy here.

A visit to the historical center or a climb up the Torre Grossa tower is a great way to get a feel for the town. But don't stop there. Enjoy the local gelato, explore the charming alleyways, visit the Duomo church, or find a local trattoria (restaurant) and enjoy a glass of Vernaccia di San Gimignano (the local wine).

Spending a day in this beautiful hilltop town will not disappoint.

3. Anghiari

This hilltop town is a bit off the beaten path but worth the visit.

Anghiari, located in the Province of Arezzo, offers beautiful views and architecture and is well-preserved by friendly locals and merchants. This small medieval town surrounded by its 13th-century walls feels ancient yet charming.

Anghiari is considered one of the "most beautiful towns of Tuscany" by CNN. If you plan a journey to Arezzo, I highly recommend stopping in Anghiari.

4. Cortona

Cortona is one of my favorite towns in Tuscany and a great place to stay for a few days to explore the region. Famous for its appearance in "Under the Tuscan Sun" by Frances Mayes, this rustic town feels like "slow Italy." It's a place where you can wander the narrow streets, enjoy a cappuccino, and become part of the local culture.

It has a slower feel, especially after the day-trippers leave town in the evening. The views out over the valley and of Lake Trasimeno are picturesque. The Piazza della Repubblica's main square is a great place to sit on some steps, relax, enjoy the local scene, and do some fine people-watching.

5. Montalcino (or Montepulciano)

Most people visit Montalcino, or Montepulciano, for the world-renowned Brunello dark red wine. If you are a wine lover, you will not be disappointed. Vineyards and the quintessential Tuscan beauty surround these two towns.

Montalcino is worth the visit with its hilltop location, charming old town feel, traditional Italian cuisine, and friendly locals.

The two towns are located about 26 miles from one another, should you want to plan a visit to both on the same day. There are great things to see along the way as well. Check out a local winery tour to immerse yourself further into the wine country.

Bonus Hilltop Town . . . Volterra!

Volterra is just a few hours' drive from the bustling city of Florence. It is a great day trip away from the crowds. It feels like this town doesn't get the credit it deserves. It isn't as busy as the more popular hilltop towns and is less traveled by visitors.

The town of Volterra is a great way to experience Italy's rich past. It feels like taking a step back in time.

I hope you enjoyed 5 of my favorite hilltop towns of Tuscany. Wherever the road may lead you, I wish you safe and enjoyable travels.

Ciao, my friends!

XOXO

Marla