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Tuscan Road Trip: Hilltop Towns and Medieval Charm

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@tripuntraveled

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𝐃𝐫𝐒𝐬𝐑𝐭𝐒 | Road Trips & Unique Places, Pienza
road trip
medieval towns
hilltop villages
wine country
cypress views
renaissance architecture
countryside views
historical sites
wine tasting
tuscan landscapes
8 places on the map
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8 places in Tuscany: Pienza, Volterra, San Gimignano, and 5 more. Every place is verified on Google Maps, featured in an Instagram post by 𝐃𝐫𝐒𝐬𝐑𝐭𝐒 | Road Trips & Unique Places.

Pienza

Pienza

Place

Discover this ideal Renaissance town, known for its soft, golden, and romantic charm. Pienza's historic redesign will make you fall in love with Tuscany.


Volterra

Volterra

Place

Explore ancient Etruscan roots, Roman theatre, and medieval streets here. Discover unique alabaster shops, giving the town a distinct ancient, mysterious feeling.


San Gimignano

San Gimignano

Place

Experience the 'medieval Manhattan of Tuscany' with its 14 surviving towers. Visit early or late to avoid crowds and fully appreciate the iconic skyline.


Horti Leonini

Horti Leonini

Garden
Garden
star
4.4

Explore these beautifully preserved 16th-century Italian gardens, a perfect example of Renaissance design. Enjoy a peaceful stroll among its geometric layouts and ancient trees.


Montalcino

Montalcino

Place

Indulge in Brunello wine tasting and enjoy impressive fortress views. This town is perfect for a leisurely countryside meal.


Chapel Vitaleta

Chapel Vitaleta

Church
Church
star
4.6

Visit this iconic and picturesque chapel, set amidst the stunning Val d'Orcia landscapes. It's a prime spot for photography, especially with the surrounding cypress trees.


Certaldo

Certaldo

Place

Discover this underrated, small, brick-colored, and quiet hilltop town. Take the funicular up for stunning views and explore its connection to Giovanni Boccaccio.


San Quirico d'Orcia

San Quirico d'Orcia

Place

Experience beautiful, unreal landscapes near iconic cypress trees and the Chapel of Madonna di Vitaleta. Explore the Horti Leonini for a tranquil escape.

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