Tuscany, the land of rolling hills, world-renowned winemakers, countryside villas, and fabulous cuisine. The region itself is actually quite large and diverse. Ranging from the pristine agricultural landscape of Val d’Orcia, fabulous stretches of beaches in Maremma, to Renaissance and Medieval hilltop towns like Montalcino. There are popular choices, such as the region’s capital, Florence, and the Leaning Tower of Pisa. All, of course, fabulous places to visit. But I always recommend venturing beyond the main cities and sites. These seven towns and villages are not only beyond charming, but great places to discover local life, tradition, and Italian cultural heritage.

charming towns in Tuscany


1. Montalcino –

Of course home to the famed, Brunello di Montalcino, this hilltop town is the perfect place to explore, shop, and witness sweeping views of vineyards and olive groves. Spend a few hours exploring the city center, then head off to one of Montalcino’s wineries for the full experience.

charming towns in Tuscany

2. Pienza –

This may be one of the most darling towns you could visit in Tuscany. From local, Pecorino cheese shops, quirky boutiques, wine tasting rooms, and of course, the walkway along the edge of the town that is the perfect spot to sit down for an espresso while admiring the panoramic valley views of Val d’Orcia.

READ MORE – Where to Eat, Drink & Explore in Val d’Orcia, Tuscany

3. Siena –

A historic town and UNESCO World Heritage Site, wander the narrow winding streets, stumbling between local shops and wine tasting rooms. The Cathedral is also a must-see while in Siena for a completely awe-inspiring experience. Siena is famously known for hosting the world-renowned horse race, Palio, which occurs twice a year on July 2 and August 16. If you are able to visit during this time, it is truly a lifetime experience.

4. Bagno Vignoni –

One of the smaller villages in Tuscany, but it sure makes up for what it lacks in size with character. This quaint town is quite unique considering the main square is centered around a once thermal pool that is fed from the nearby natural hot spring. Although it is no longer permitted to swim in, there are spa and wellness hotels in the town, lovely restaurants, and wine bars. If you are looking to stay in a quieter part of Tuscany, this the perfect escape full of fabulous food, wellness facilities and nearby wineries.

READ MORE – Luxury Hotel Edition: Albergo Posta Marcucci

where to stay in Tuscany

5. Volterra –

A Medieval hilltop town first inhabited by the Etruscans, and then the Romans. The red brick and orange rooftops create the perfect contrast with the surrounding greenery. From the ancient Roman theater, gorgeous Cathedral, 4th – 5th-century city walls, and peculiar layout of narrow streets, Volterra offers a fascinating look into the region’s history.

6. San Gimignano –

Considered a UNESCO World Heritage Site, this town of towers is a stunning example of medieval architecture and urban layout. This strategically placed town, between Florence and Siena, was once a major hub for pilgrims traveling along the Via Francigena from Canterbury to Rome.

7. Lucca –

Located in the northern part of Tuscany, Lucca was once an important meeting place for Julius Caesar during ancient Roman times. Today, enjoy yourself in Piazza dell’Anfiteatro, a square built on the remains of an ancient Roman amphitheater, hence the curved shape of the urban gathering point. Lucca is also conveniently located near Pisa and the beaches along the Versilia coast.

8. Porto Ercole –

Not the typical Tuscan landscape, this beachside town is located in Tuscany’s western region of Maremma. It is the best of both worlds for a summer escape to Tuscany, a peaceful escape, great wine, and ocean access. Think beachside bliss, stunning ocean views, and Super Tuscan wines.

READ MORE – A Summer Guide to Beaches in Tuscany

ready to experience your dream trip?


  1. Aletha Moffatt on April 10, 2019 at 3:05 am

    It’s a pity you don’t have a donate button! I’d without a doubt donate to this fantastic blog! I suppose for now i’ll settle for bookmarking and adding your RSS feed to my Google account. I look forward to brand new updates and will talk about this blog with my Facebook group. Chat soon!

    • Lexi Doerfler on April 12, 2019 at 5:54 pm

      That is so sweet, thank you! Well if you ever need help with planning a trip, you know how to find me.

  2. accounting breda on May 5, 2019 at 1:49 pm

    Wonderful items from you, man. I have remember
    your stuff prior to and you’re just too wonderful. I really like what you have acquired here, really like what you’re saying and the
    best way wherein you are saying it. You’re making it entertaining and you continue to care for to stay it wise.

    I cant wait to learn much more from you. That is actually a wonderful website.

    • Lexi Doerfler on May 8, 2019 at 6:16 pm

      Thank you so much. Love the positive feedback.

Leave a Comment

Read More Posts