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Tuscan Fairytale Towns Perfect for A Road Trip

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@tripuntraveled

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𝐃𝐫𝐒𝐬𝐑𝐭𝐒 | Road Trips & Unique Places, Pienza
hilltop villages
medieval streets
cypress-lined roads
storybook towns
renaissance town
val d'orcia views
pecorino cheese
etruscan history
medieval towers
walled village
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5 places in Tuscany: Pienza, Volterra, San Gimignano, and 2 more. Every place is verified on Google Maps, featured in an Instagram post by 𝐃𝐫𝐒𝐬𝐑𝐭𝐒 | Road Trips & Unique Places.

Pienza

Pienza

Place

Discover this perfect Renaissance town, celebrated for its charming streets and panoramic Val d’Orcia views. Don't miss sampling some of the best pecorino cheese Italy has to offer while exploring. Enjoy a leisurely stroll and soak in the historical ambiance.


Volterra

Volterra

Place

Step back in time within this medieval gem, rich with ancient Etruscan history. Wander through stone alleyways for a more mysterious, old-world experience. Explore the ancient ruins and absorb the timeless atmosphere.


San Gimignano

San Gimignano

Place

Marvel at the famous medieval towers that give this town an unreal, cinematic appearance. From a distance, it's a sight to behold, and walking its streets feels like stepping onto a movie set. Climb one of the towers for breathtaking panoramic views of the Tuscan countryside.


Certaldo

Certaldo

Place

Discover this tiny, oft-skipped walled village, offering stunning panoramic views and charming brick streets. Its underrated historic center provides an authentic glimpse into medieval life. Take the funicular up for easy access and enjoy a quiet exploration away from the crowds.


San Quirico d'Orcia

San Quirico d'Orcia

Place

Experience one of the prettiest stops in Val d’Orcia, surrounded by quintessential Tuscan landscapes. Cypress roads and golden countryside create a dreamy backdrop for exploration. Visit during golden hour for truly magical photo opportunities.

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