See The Hilltop Towns Of Tuscany On A Day Trip From Florence

There are lots of things to love about Tuscany. From the fresh food and fine wines, to the artistic heritage and scenic landscapes, it’s easy to see why so many holidaymakers fall head over heels for this Italian province. 

The cultural gem of Tuscany is undoubtedly Florence and you certainly won’t be short of things to do and see if you base yourself in the city. Not only is it home to some absolutely stunning museums and monasteries, but it’s centrally located – meaning that you can easily visit some of the region’s historic hilltop towns during a day trip from Florence. 

Here are some of the best that you won’t want to miss.

San Gimignano

The silhouette of San Gimignano has deservedly risen to fame across the world: its fourteen iconic towers have gifted the town the nickname of ‘The Manhattan of the Middle Ages’. These thirteenth century constructions didn’t just serve a military purpose (their height granting a superior defensive position), but also doubled as a spectacular symbol and display of power and wealth. 

If that hasn’t already convinced you to add San Gimignano to your list of day trips from Florence, its historic centre should. Wandering these perfectly preserved medieval streets truly captures the imagination and transports you back in time. It’s an experience not to be missed.

Monteriggioni

Perched atop a low, oval hill, Monteriggioni is surrounded by high medieval walls. The hamlet was originally founded as a defensive outpost by Siena as a protection against attack from Florence. Today, you can stroll along the top of the defences and admire the iconic Tuscan scenery. Kids will also be thrilled with the Armoury Museum, where they can learn about the town’s old fortifications and weapons, and even try on a heavy medieval helmet. 

Certaldo Alto

Certaldo Alto is perfectly situated for a day trip from Florence. It lies just a half hour’s journey away, and is sure to charm travellers with its quaint appearance and relaxing atmosphere. 

Despite Certaldo Alto’s small size, there are still a couple of must-see attractions for you to discover. Fans of classical literature will be pleased to find the house which once belonged to Boccaccio, the medieval poet. The Palazzo Pretorio also has frescoes and other archaeological artefacts on display for you to peruse, and from the top you’ll be able to enjoy sweeping views over the hills.

Radda in Chianti

Wine lovers will delight in the vineyards and cellars of Radda Chianti. The rolling countryside here is truly breath-taking. 

This destination is best for holidaymakers who enjoy long strolls, picnics, and getting a taste of the local culture. There is little sightseeing to do, but that is more than made up for by the delicious wine and the views. For those travelling in May, this small town also hosts the Radda nel Bicchiere Wine Festival.

To really get the most out of your visits to these charming hilltop towns in Tuscany, your day trips from Florence are best booked with a reputable tour operator. Local guides can teach you more about Tuscan history, introduce you to aspects of their culture, and can highlight excellent recommendations for places to go, see, and eat during your stay.

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Mauro Bramante is the Director of WalkAbout Florence, an independent business offering unforgettable tours and excursions around Italy including great itineraries for a day trip from Florence. Whether you want to ride a Vintage Vespa, try the famous Chianti wine or get cooking with fresh local ingredients, Mauro's company promises excitement, adventure and above all, fun. If you're keen to experience the magic of Italy with the help of some passionate and knowledgeable tour guides, look no further than WalkAbout Florence for your next getaway.