7 of Tuscany’s Most Unmissable Towns

by Chris Allsop  |  Published October 30, 2018

Tuscany is so overburdened with beguiling destinations that to stop at just Florence and Siena is to do yourself a disservice. Instead, hire a vintage Fiat 500 and explore the galaxy of gorgeous towns enfolded in its rolling hills – here are seven of our most unmissable. 

Head into the hills to find some of Tuscany’s most engaging sites (Photo: Chris Allsop)

San Gimignano

Known as ‘the Town of Fine Towers’, San Gimignano has a postcard skyline silhouette better suited to a modern metropolis than a medieval town. While only thirteen tower-houses remain standing, in its medieval heyday there were somehow a total of 72 crammed inside of its stone walls, each an ostentatious display of wealth by a powerful local family. This medieval  ‘Keeping up with the Joneses’ is a useful metaphor for medieval Italy as a whole, where wealthy city-states packed into the peninsula vied jealously against their neighbours. Walking San Gimignano’s ancient streets  summons a sense of that past, and it’s little wonder the town, situated roughly in the middle between Siena and Florence, has been a UNESCO World Heritage Site for nearly thirty years.

Where to Stay: Hotel la Cisterna (

This well-kept three-star (with an admittedly unfortunate name) is superbly situated on the main square of town. Friendly staff and well-kept rooms – most decked out in charming, slightly dated Florentine style – make for a great stay (if not the cheapest the town has to offer). Ask for a room with a balcony and a view of the hills, if available.


It’s hard not to like Montepulciano, a long strip of Tuscan stone perfection south of Siena containing a scattering of peaceful squares and ancient palazzi. Its positioning, at 600m, ensures textbook Tuscan views from your B&B balcony as you sip a glass of the eponymous Vino Nobile. While most of the towns on this list will probably act as brief visits or stop-offs en route to the next thing, Montepulciano offers a deeper trove of interest; besides the possible winery tours, the town offers much for the Renaissance admirer to nosy into (not to mention fans of vampire-romance slush, Twilight, which was partly filmed here). Montepulciano also acts as an excellent base for exploring the UNESCO Val d’Orcia countryside (essentially unfiltered Tuscany).

Where to Stay: Trattoria di Cagnano B&B (

Found on a street corner in the centre of town, this is a great value B&B for its location. Rooms are cheerful and clean with just enough frills, while the staff are friendly and the traditional trattoria situated downstairs makes for tasty eats with a side of good people watching (at the outside tables).

The view of Monteriggioni (Photo: Chris Allsop)


Famous for its intact medieval wall sprouting 14 guard towers, Monteriggioni sits on its strategic hill-top looking not entirely unlike a Da Vinci’s stab at a flying saucer. Circular and imposing, the town was originally built as a defensive fortress on the approach to Siena. Today it’s a UNESCO heritage site with its main Piazza Roma filled with tourists, artisan shops and gelato. Naturally the thing to do is walk the walls (the cost is €2.50) and imagine yourself as sentry trying not to be distracted by the pretty hills as the enemy approaches (currently only the north side of the ramparts can be walked due to renovations (check for updates)).

Where to Stay: Agriturismo Ebbio (

There is a perfect pleasant B&B overlooking Monteriggioni square, but with such stunning countryside visible from the walls it might be a missed opportunity not to stay at Ebbio agriturismo –  a working organic farm about ten minutes-drive from the famous walls. With structures dating back to the 13th century, expect a warm welcome and elegant, rustic accommodation. The meals also cater for vegetarian-friendly travellers.


For the lover of Renaissance architecture, UNESCO-stamped Pienza – located in the Val D’Orcia about 15 kilometres from Montepulciano – is pretty pickings indeed. Pope Pius II ensured his local legacy when he converted the anonymous village of his childhood into a template for humanist urban reorganization (unfortunately for him, he died before the task was complete). There’s more than enough beautifully preserved Renaissance architecture here for a day’s visit, leaving a little time to idle along the romantically named streets (‘Via dell’Amore’, for example) or, if you’re defiantly single, pick up some of the renowned pecorino instead. Being of such cultural, architectural, and romantic importance, Pienza does become crowded on weekends.

Where to Stay: La Bellavita Pienza (

Good value B&B with clean and comfortable rooms that can get a bit more lux if desired. Well positioned near the town’s historical heart, views from the windows include Pienza’s splendid renaissance buildings as well as the surrounding countryside. That all-inclusive panorama gets even better on the cosy rooftop terrace where you can take breakfast or, for sunset, your bottle of Montepulciano.

The view from Lucca’s Guinigi Tower (Photo: Chris Allsop)


Enclosed within massive and intact medieval walls, Lucca was made into one of the richest cities in Tuscany by its canny merchant class.  While you’ll find a maze of unusual churches, high-end boutiques and inviting cafes at ground level, Lucca saves its best for slightly higher up. Hire a bike and cycle along the top of the wide medieval walls. Small, shady parks coalesce in the corners of these graceful fortifications, where locals play chess, work on laptops, or apparently profess passionate declarations of undying amour no matter how many families are picnicking nearby. Be sure to hike up Guinigi Tower (entry is only a few euros) as its panoramas at its arboreal summit are glorious.

Where to Stay: Hotel Palazzo Alexander (

Eye-popping décor and good value rooms are a winning combination at Hotel Palazzo Alexander, a family-run hotel located within Lucca’s centre and yet managing to feel somehow secluded. The staff are gracious and attentive, and on point with their local restaurant suggestions.

The view from Castellini in Chianti’s museum rooftop. (Photo: Chris Allsop)

Castellina in Chianti

A must for the wine drinkers, this handsome, sun-bleached town is – as the name attests – buried in the vine-stitched hills of the Chianti wine region. The wine, which became synonymous with cheap bulk production has since refined its act to become one of the most reliably tasty, good value drops in the world. Naturally the town has an abundance of genial wine shops offering tastings of Chianti Classico – just the thing to put you in the mood for a wander of its medieval defensive walls with expansive views of the hills. The town also has an interesting, if rather bijou, museum housed in a stout 14th century fortress covering some of Castellina in Chianti’s 3,000 year-old history.

Where to Stay: Villa Cristina (

A family-run B&B a short walk to the town’s historic, wine-filled centre, Villa Cristina offers light-filled doubles, splendid views, tasty cakes, and a swimming pool – all for one of the most competitive prices around.


As you approach Pitigliano, a town located near Tuscany’s southern border in the undeveloped region of Maremma, its stone buildings seem to rise organically from the volcanic plateau on which this 2,000 year-old town sits. It’s a breath-taking introduction to this off-the beaten track gem known as ‘Piccola Gerusalemme’ or Little Jerusalem for its long-standing Jewish community. Its warren of an old town is easily explored in a half day visit (longer if you get lost…). Fabulous views are found on the walkable defensive walls and be sure to explore the Jewish Quarter and its chequered history.

Where to Stay: Albergo Guastini (

With something of a monopoly as the only hotel located in Pitigliano’s old town, you might think that Albergo Guastini could charge high and deliver low. Fear not – solid value rooms are backed up by quality service and a restaurant with awe-inspiring views of the town’s defensive walls.