Don’t miss these charming villages in Tuscany, Italy 🥹

‼️The Tuscany road trip you will think about forever👇🏻

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This is the route I would actually do if you want medieval towers, hilltop towns, wine villages, cypress roads, Renaissance streets, and countryside views.

📍Volterra
Start here if you want Tuscany with an ancient, mysterious feeling. This town has Etruscan roots, a Roman theatre, medieval streets, and alabaster shops that make it feel completely different

📍San Gimignano
This is the famous medieval Manhattan of Tuscany, with 14 surviving towers still rising above the town. Go early or later in the day because this one gets busy, but the skyline is absolutely worth seeing once in your life

📍Certaldo Alto
This is one of the most underrated stops on this route. It is small, brick colored, quiet, and tied to Giovanni Boccaccio, the author of The Decameron. Take the funicular up

📍Montalcino
Come here for Brunello wine and fortress views. This is a good stop for wine tasting or a long countryside meal.

📍San Quirico d’Orcia
Beautiful and unreal close to the famous cypress trees, Chapel of Madonna di Vitaleta, Horti Leonini, and some of the most iconic Val d’Orcia landscapes.

📍Pienza
End here for the soft, golden, romantic version of Tuscany. Pienza was redesigned as an ideal Renaissance town, and will make you fall in love with Tuscany.

🚗 How to plan this route
Do not try to squeeze all of this into one rushed day unless you enjoy suffering beautifully.

Day 1 – Volterra, San Gimignano, Certaldo
Day 2 – Montalcino, San Quirico d’Orcia, Pienza

But if you have more time, make it 3 days and stay overnight in the countryside.

📌 Save this for your Tuscany trip because this route gives you the best mix of medieval towns, wine country, cypress views, and more.

Ask any questions👇🏻

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