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Must-See Towns of Tuscany

If you ever have the opportunity to visit Tuscany, take it. The vast, hilly, wine-filled countryside of Italy is a step back in time: ancient hilltop towns surrounded by walls, cobblestone streets, a culture of food, family, art, and music. I'm going to share with you three of the towns I had the pleasure of visiting during my time in Tuscany.

Cortona

Cortona was the perfect home base for our time in Tuscany. Most well-known as the Under the Tuscan Sun town, its piazzas are always full of friendly people, sitting on the steps chatting or sipping on an afternoon spritz at one of the many cafés. Its streets are home to numerous family-run restaurants and independent shops selling chic clothing, Italian wine and olive oil, hand-crafted leather goods, and more. 

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Siena

This much larger town is rich with history and beautiful architecture. Its main town square, Piazza del Campo, is known for being the location of the bi-annual Palio horse race and is also a UNESCO World Heritage Site. I recommend having a seat of one of the many cafés lining the circular piazza, having a coffee, and doing some people-watching.

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Once you've had your fill of that, head on over to Duomo di Siena, a Gothic cathedral and architectural work of art filled with many more pieces of art by some folks you may have heard of - Michelangelo and Donatello, among others. I marveled at the insides for an unexpectedly long amount of time.

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Next, wander over to Duomo Nuovo, purchase a ticket, and climb up to the Panorama del Facciatone viewpoint via 131 steps (complete with narrow spiral staircase - maybe not the best activity for the highly claustrophobic or acrophobic). The 360 degree views from the top are astounding and well-worth the climb. You'll look back down on the Duomo di Siena, over to the Torre del Mangia (super tall, skinny tower) and Piazza del Campo, and down on the many beautiful rooftops surrounding you. Take a million pictures before heading back down.

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Walk back to Piazza del Campo, pick a restaurant (any restaurant) and enjoy a delicious pizza and an Italian beer and relax for the rest of the afternoon.

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Montepulciano

This medieval hilltop town is known for its red wine, vino nobile, and rightfully so. Reds from the Montepulciano region are my favorite Italian wines. I learned this after a fun and informative wine tasting and cellar tour, which I highly recommend doing while in town.

When visiting, you'll park in one of the many parking lots surrounding the town and will have to walk up the very steep streets until you reach the main square. We spent the day mostly wandering the pretty streets and taking photos, having lunch at a nice restaurant along the wall (thusly with sweeping views of the surrounding landscape), and trying wines. I definitely recommend walking through the cellar on a self-guided tour of Cantina De Ricci and then partaking in their tasting. Then every time you see a Montepulciano wine on a menu in the future, you'll get really excited that you've tasted it at its source. Or maybe that's just me (but probably not).

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Another charming town that we passed quickly through and didn't get to spend enough time in was Lucca, which I recommend at least a walk-through as it is one of the more unique places I saw, being flat yet still surrounded by a very large wall that you can walk on top of. 

Tuscany is one of those places I could return to time and time again and never tire of. Its sun and food and classic beauty and architecture and food (yes, I said food twice) foster a specific feeling of contentedness that I haven't found elsewhere. 

If you have any questions or want to share your experiences or other Tuscan towns that we need to visit, please feel free below!