Discover the best small towns to visit if you’re based in the Arezzo area. From all-time favourite Cortona and Montepulciano to Medieval hamlets and hidden gems like Loro Ciuffenna and Castiglion Fiorentino. These are scenic ancient towns – located not more than an hour from Arezzo, in Eastern Tuscany – that offer interesting sights, a few small museums and a pleasantly tranquil atmosphere.

10 Picturesque Small Towns to Visit near Arezzo

1. Montepulciano

Famous for being the place where the revered Nobile di Montepulciano Wine is produced, the hilltop town of Montepulciano overlooks the Valdichiana, offering splendid views, one of Tuscany’s most handsome squares, plenty of lovely shops and restaurants where you can try out the local fare. And, of course, wine lovers will find paradise in any one of the cellars that offer exclusive wine tasting experiences.

hilltop towns tuscany
Montepulciano, the main square

2. Cortona

If you’ve ever read “Under the Tuscan Sun” you’ll have heard of Cortona. A town that is undoubtedly one of the highlights of Tuscany . History buffs can explore the Etruscan Museum, awe at the massive Etruscan walls that still embrace the town, enjoy 15th century art in the Museo Dioceziano, and look out for the Medieval houses in Via Jannelli. The views over the Valdichiana and the lively atmosphere, that reigns all year round, will do the rest.

=> Top 20 Experiences in Tuscany

3. Anghiari

One of the most scenic walled towns in Tuscany, Anghiari is a Medieval gem that is welcoming and full of surprises. It has always been renowned for its artisans’ skills. Still today the picturesque streets of Anghiari are lined with pottery shops, antique sellers and restoration workshops. Highlights include ancient churches and the Museo delle Arti e Tradizioni Popolari (Artcrafts and Folk Traditions Museum).

Nearby => If you love art, don’t miss to visit the Piero della Francesca works in San Sepolcro and Monterchi => see our Piero della Francesca itinerary.


4. Castiglion Fiorentino

Leaving the well-trodden tourist trail behind, we explore the delights of Castiglion Fiorentino, still surrounded by Medieval walls. The main access is though Porta Fiorentina, the massive stone door restored in the 19th century. The heart of the town is the Piazza del Municipio, with the elegant Renaissance loggia, and sights include the Medieval Church of San Francesco, the tower (Cassero), and the Pinacoteca with a collection of paintings from 14th to 17th century.

5. Poppi

We have a soft spot for Poppi, the main town of the Casentino area, located 35 kilometres north of Arezzo. Dominating this small hilltop town is the striking Conti Guidi Castle, that has an impressive history and is visible from kilometres away as you drive around the valley, giving Poppi a very impressive silhouette indeed. The castle itself is well worth the trip to this out-of-the-way part of Tuscany, and if you spend a few days in the area you can explore the Casentino area with its suggestive forests and monasteries.

=> See the Best of Tuscany in 3 Days: a complete Itinerary

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Poppi dominating the Casentino Valley

6. Lucignano

Located in the Valdichiana, between Siena and Arezzo, Lucignano is a favourite destination for couples. Its top attraction is the renowned Tree of Love, that tradition claims brings good luck to anyone who is in love. It’s a masterpiece of Gothic jewellery in the shape of a tree, decorated with coral and rock crystal, hosted in the Palazzo Comunale Museum. In Lucignano, make sure you visit the frescoed Church of San Francesco and the Collegiata.

Nearby => the fortified Medieval hamlet Gargonza Castle is an enchanting place to spend the night or have a meal.

=> Find out The Top Romantic Destinations in Tuscany!

7. Loro Ciuffenna

Located in the Valdarno, near the motorway that goes from Florence to Arezzo, Loro Ciuffenna is a picturesque pastel-coloured village with a serene timeless atmosphere. Ciuffenna is the name of the river that crosses the town and provides water for the mills that dot the area. Among these is one of the most ancient water-mills in Tuscany, is still in use today for grinding the local chestnuts (to make the traditional chestnut flour). Visit the small art museum that hosts the works by local 20th century artist Venturino Venturi.

Nearby => Don’t miss to visit the delightful Romanesque country church Pieve di Gropina. Il Borro Relais (owned by the Ferragamo family) for a unique wine experience.

small towns to visit near Arezzo
Loro Ciufenna – Image by Grzegorz Golebiowski Wikipedia

8. Bucine

One of Tuscany’s “CittàSlow”, Bucine is a place where ‘the good life’ is taken seriously. This whole area of Valdambra is well-known for the quality of the food, the serene landscape and ancient pievi (country churches), witnesses of a rich past. It’s a way to get away from it all and rediscover a more gentle rhythm of living. Attractions in the area: Pieve San Giovanni Battista a Galatrona, Galatrona Tower, Chiesa di San Pietro di Badia a Ruoti, town of Ambra and San Pancrazio.

9. Ortignano Raggiolo

A tiny village near the Pratomagno mountain range, surrounded by chestnut trees woods. The stone houses embrace the small square with the Church of San Michele, an ancient edifice with a Gothic-style facade. Atop the village you can see the ruins of what’s left of the Medieval Count Guidi Castles. Intrepid travellers come here to find peace, silence and to hike in the woods.

=> Discover 12 Amazing Hilltop Towns in Tuscany and some Fairy-tale Places in Tuscany to explore.

small towns to visit near Arezzo
A view of the Valdambra – Image by DeBlu68 Wikipedia

10. Foiano della Chiana

The small town of Foiano della Chiana is famous for its traditional Carnival that takes place every February. The amazing allegorical floats compete with the one in Viareggio, and animate the streets of the town with parade that has its origin in the 16th century. The historic centre has some interesting churches: Church of San Francesco, Collegiata di San Martino, Chiesa San Michele. While you’re there try the Chianina (the top-quality local meat variety) and the Chianti Colli Aretini red wine.

Nearby => Shopping enthusiasts must visit the renowned Outlet Valdichiana, with famous brands that offer great discounts.

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=> Best Tuscan Traditional Festivals