Hilltop towns. A Medieval atmosphere. Narrow stone lanes and lovely squares. Tuscany is filled with them. Here we look at five destinations that are perfect for a trip in autumn, when the colours of the Tuscan countryside do their best to impress us.

Which scenic small towns should you visit in Tuscany in Autumn?

SAN GIOVANNI D’ASSO. Try out the truffles in the magical landscape of the Crete Senesi

In the heart of the Crete Senesi, just 27 kilometres south of Siena, lies San Giovanni d’Asso. A village that hosts an important Truffle Festival each November. It’s heaven for lovers of this prize fungus, and for those who can’t get enough of it, there’s also a Truffle Museum in the castle that’s open all year round. Near the castle, the lovely Romanesque Church of San Pietro a Villore is well worth a visit.

scenic small towns to visit in tuscany in autumn

San Giovanni d’Asso is a perfect base from which to explore the surrounding Crete Senesi, a place with a singular and hauntingly beautiful landscape. Think low clay hills, vast expanses of grey, white and burnt yellow, and cypress trees casting long shadows over the fields.

Highlights: Truffle Museum inside the Medieval Fortress, Romanesque Church San Pietro a Villore, exploring the Crete Senesi. Nearby, the tiny Medieval hamlet of Lucignano d’Asso.

=> Love food? Check out the Best Autumn Food Festivals around Tuscany!

RADDA IN CHIANTI. Vineyards as far as the eye can see

While the new wine is being produced, the vine leaves put on their yellow and orange autumn shades. And Radda sits on a hill above it all, in the midst of a gorgeous landscape of woods and vineyards, offering magnificent views.

Once the capital of the historic Chianti League, founded to defend Florentine territories against Siena, Radda is today the capital of wine making. It’s amongst the most scenic towns in the Chianti area, filled with lovely shops and enoteche for wine tasting. Driving around this area in autumn is a delight.

⇒ Check out our Chianti driving itinerary.

Highlights: Main square Piazza Ferrucci with Palazzo del Podestà, Wine tasting in one of the local wineries, Driving along the Chiantigiana road.

chianti italy

ANGHIARI. Autumn delicacies and a Medieval feel

The scenic hilltop town of Anghiari is in the Valtiberina, north-east of Arezzo in eastern Tuscany. During the months of autumn it celebrates local food. And every year it hosts the Festival ‘Cento Gusti dell Appennino’  (usually it takes place on the last weekend in October, dates for 2023 haven’t been confirmed yet) and the Festival of San Martino and Bringoli (usually on the second weekend in November), during which you can try, among other things, the thick hand made spaghetti or ‘bringoli‘ with mushroom and meat sauce.

10 Things to do to enjoy Autumn in Tuscany!

Tuscany is very much about local specialities and seasonal delicacies. So to truly experience the Tuscan spirit there’s nothing better than to attend one of the food festivals, dedicated to locally produced products. And Anghiari has got much more on offer, for shopping and art enthusiasts.

Highlights: Anghiari boasts a lovely Medieval centre, with plenty of artisan shops. Palazzo Taglieschi hosts an interesting museum about the area.

⇒ Discover the best Autumn destinations in Italy!

=> See more trip ideas for November in Tuscany.


POPPI. A castle, and the best fall foliage viewing in Tuscany

The Foreste Casentinesi National Park is the perfect choice for travellers in search of autumn colours. You’ll find it in eastern Tuscany, near the border with Emilia-Romagna. An area covered in a thick forest of oaks, beech and maple trees.

Poppi, with its imposing Medieval castle, is the main town of the Casentino area. Visiting it in autumn is a real treat, because its already scenic position is highlighted by the colours of the surrounding woods.

Highlights: Conti Guidi Castle, Foreste Casentinesi National Park.

⇒ More ideas for a trip to Tuscany? Find out about more special autumn destinations in Tuscany, and the perfect 5 day itinerary.

=> Check out the Best Places to see Fall Foliage in Tuscany!


Barga, chestnuts and mushrooms in the Garfagnana

Another hilltop town blessed with a lovely location is Barga, in the Garfagnana area, in northern Tuscany. This is a mountainous area between the Apuan Alps and the Appennines. A land of verdant woods, small stone hamlets and charming lakes. Not to mention lots of delicious chestnuts and mushrooms.

If you visit Barga in autumn you have a chance to try some of the delicacies made from chestnut flour, for which the area is famous. Cakes, crepes with ricotta (‘necci’), and chestnut jam. Or maybe you favour porcini mushrooms and can’t wait for a sauce made with fresh funghi. A real treat.

Highlights: The splendid Romanesque Cathedral, explore the narrow streets of Barga and enjoy the views of the valley.

What to Wear in Tuscany in Autumn.

=> What to do in October in Florence: best events and festivals

And…in case you need more inspiration to plan your autumn trip to Tuscany, have a look at our article with more reasons why this season is so special in this part of the world.