As one of the most popular regions for a villa holiday, Tuscany is a firm favourite with our Bookings For You guests. But with so many incredible towns, cities and villages in the region, it’s hard to know the best place to choose as a base. Here is our pick of the top five towns in Tuscany to use as a base for your 2025 Tuscany villa holiday.
1. Cortona
While Cortona may have been made famous by Frances Mayes’ book Under the Tuscan Sun, there is so much more to this Tuscan gem. Elevated 600 metres above sea level, the views from Cortona are arguably just as impressive as the town itself. Dating back as far as the Etruscan period, Cortona is steeped in history, and visitors are richly rewarded when they visit.
Discover our Cortona travel guide for more inspiration on what to see and do in this magnificent Tuscan city.
2. Lucca
Lucca is compact enough that it is easy to discover in a day. However, if you stay longer, you’ll be extremely thankful that you did! The city is probably most famous for its walls, but within them, there are some real gems to discover. Affectionately known as the ‘city of one hundred churches‘, we always lose count of the number of religious buildings we see each time we visit Lucca! But the number of wonderful restaurants in Lucca is just as impressive. And trust us, you will be grateful for the chance to sample more of them than any 24-hour visit will allow.
Read our Lucca travel guide for more inspiration on what to see and do in this wonderful Tuscan city.
3. Volterra
Volterra may be slightly more off the beaten track than both Cortona and Lucca, but it certainly makes up for it with its charm. Today, Volterra is recognised mostly thanks to Stephenie Meyer’s popular Twilight series of books. However, just like Cortona, its history dates back to the Etruscan period and there are a number of Etruscan and Roman remains to discover. These include the Etruscan Acropolis at the top of the town and the 1st century Roman theatre lower down. But its more recent history is pretty impressive too. Volterra is home to one of Europe’s oldest museums, along with what is believed to beTuscany’s oldest town hall.
Check out our Volterra travel guide for more inspiration on what to see and do in this magical Tuscan city.
4. Montepulciano
Tucked in the rolling hills of southern Tuscany, Montepulciano is surrounded by the dramatic landscape of the Val d’Orcia. A wonderfully charming hilltop town filled with cobbled streets, pretty piazzas and a mix of Renaissance and Gothic architecture. Yet despite its charm, Montepulciano is possibly more well-known for what grows in the fields that surround it than anything you will find within its ancient walls. Here, the sangiovese grapes have been used for generations to create one of Tuscany’s greatest red wines: the Vino Nobile di Montepulciano.
Discover our Montepulciano travel guide for more inspiration on what to see and do in this stunning Tuscan city.
5. Pienza
Pienza has had UNESCO World Heritage status for nearly 30 years now, quite remarkable for a tiny village in the heart of the Val d’Orcia. We don’t think Italian villages get much prettier or more perfect than Pienza. What’s more, we think Pienza is home to some of Italy’s most charming streets with very loveable names too. The Via dell Amore (Street of Love) and the Via dell Bacio (Street of the kiss) mustn’t be missed! While it won’t take long to explore Pienza, you certainly won’t tire of meandering through the same gorgeous streets day after day.
