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The Most Magical Hill Towns in Tuscany

Tuscany. Cypress trees lining winding driveways that ascend mossy velvet slopes leading to sumptuous wine cellars, where you can sip the wine as you look out on the vineyard it came from.

If that’s the only picture you have of Tuscany, you’re in for a surprise! Embedded across the region’s hilly landscape, you’ll find delightful towns that still revel in their medieval splendour. Car-free zones, steep and narrow cobbled lanes, red rooftops, large piazzas and ancient Etruscan caves, these towns were key players in Italian politics, religion and history. Today, they make the perfect base for your Tuscan trip, as most of them are within an hour’s distance apart. The food here is rich, rustic and pure – caves of locally made wines, sausage, cheese and honey lie in wait. The people, among the friendliest we’ve seen in Italy, and that’s some serious competition. The slow life in these towns gives birth to creative arts. Hidden in these lanes are workshops creating some of the finest pieces we’ve seen – Mosaics, Linen, Plaster, Paintings, we can see why this region has inspired so many. So tear yourself away from the more popular Pisa and Lucca like we did, and let these hill towns seduce you in every way.

Hill Towns in Tuscany

Hill Towns in Tuscany

The Most Magical Hill Towns in Tuscany

1. Siena:

The town that inspired the Crayola shade and now Instagram filter by the same name, is a beautifully rusty-brown tinged panorama of tiled roofs and cobble stone courtyards. At its centre is one of the most beautiful piazzas we’ve seen – Il Campo, with it’s sloping surface it makes the perfect spot for picnickers to rejoice and we enjoyed watching them over a sumptuous meal at Al Mangia Ristorante. Later at night, Charles was invited to the Etruscan cave at the back of the Taverna San Guiseppe (where we enjoyed a long gluttonous dinner). I could return to Siena just for the food! Check out our stay at the historical Residenza d’Epoca Palazzo Coli Bizarrini which was so much more than a hotel in Siena.

Hill Towns in Tuscany, Siena

Hill Towns in Tuscany

Hill Towns in Tuscany

2. Montalcino:

We were so glad to have friends who were driving us around, or we’d never have gotten to this cute town perched at the top of a winding road. Great for a day of walking around, we were thrilled there was none of the tourist crowd of Siena, just a couple of day trippers like us. We stepped into a couple of wine boutiques, shopped for our dinner at the wonderful open air markets, and then came upon the stunning Fortezza. Within this medieval ruin, sat the Enoteca where we spent most time. Picking the right Brunello di Montalcino was no mean feat after all. The Col d’Orcia remains my favourite Italian wine till date.

Hill Towns in Tuscany, Montalcino

Hill Towns in Tuscany

Hill Towns in Tuscany

3. Montepulciano

We were so glad we decided to stay here for a couple of days. Getting to Montepulciano from the train station would have been impossible without our AirBnB host (who is now a friend) helping us out. The higgeldy piggeldy cobbled streets were narrow and rather steep, so we got quite the workout walking around town. Remember the twilight episode shot here? There was a definite sense of rustic Medieval life after dark. The piazza here with it’s Medici well and old town hall was empty, as was the bizarre Museum of Tortura. It was a rainy weekend, and we loved opening our windows to the morning fog over the rooftops. We were the only ones insane enough to sit on the terrace of the Cafe Poliziano watching the beautiful but rainy Tuscan countryside. Befriending a plaster artisan, watching an artist create mosaic masterpieces was definitely a morning well spent as we walked around town.

Hill Towns in Tuscany

Hill Towns in Tuscany

Hill Towns in Tuscany

4. Monticchiello

This town happened to us quite by serendipity, and we were driven there by new friends who were locals. Just in time for a short stroll through town, we huffed and puffed our way while watching centenarians stooped over the sticks making the climb rather deftly. Wild gesticulating to converse with an old linen store-keeper, discovering a new artist’s display at the fort on top, it was a strange mix of fortunate circumstances which ended with a beautiful sunset enjoyed over excellent gelato with our new friends in town. All of this, overlooking the stunning Val d’Orcia (remember the dream sequence from Gladiator? Yep, that place.)

Hill Towns in Tuscany

Hill Towns in Tuscany

There were so many other towns that we’ve heard so much about, but to cover all of them in the way it should be done- slowly, would require us to spend much much longer in Tuscany. Have you been to Assissi, San Giminiano, Orvieto, Civita or any of the others? Which one’s are your favourites? (Because we know it isn’t possible to narrow it down to any one favourite of all the Hill Towns in Tuscany.

 

 

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“The Most Magical Hill Towns in Tuscany”

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