From Rome: Tuscan Medieval Towns & Winery Tour with Lunch

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Tours Culture & history Day trips Culinary & nightlife Day Trips From Reseller exclusions Day Trips To Nature & adventure Sightseeing Tours Nature & Panorama History & heritage Food & drinks Medium-risk activities

Get swept away by the magic of Tuscany's rolling vineyards, historic towns, and incredible food and wine. Join a once-in-a-lifetime day trip from Rome and visit the charming Pienza and Montepulciano.


  • Get off the beaten path in the medieval villages of Tuscany.
  • Sit down to a traditional lunch in a historic wine cellar.
  • Visit the beautiful towns of Pienza and Montepulciano.
  • Tour a local vineyard and taste regional wines.
  • Explore in a small group of just 18 guests maximum.


Your Tuscany day trip starts early so you can make the most of your time. Board an air-conditioned minibus in central Rome that will whisk you away from the busy city straight into the heart of Tuscany. Your first stop is at Monticchiello, a stunning little hillside town that makes for a once-in-a-lifetime photo op. From there, it's a short drive to your next stop: Pienza. Your expert tour guide will lead you on an introductory stroll of the town, which is famous for its Pecorino cheese (and yes, you'll get to try some for yourself!). Next, sit back and relax on a scenic drive to Montepulciano, home to your next stop: a stunning family-run winery complete with lush vineyards and a historic cellar you have to see to believe. Enjoy a guided visit of both and sit down to a homemade lunch with wine pairings for an only-in-Tuscany experience you won't soon forget. After lunch, you'll have some free time to explore the charming streets of Montepulciano at your own pace. Before returning to Rome, you'll make one additional stop at the historic San Biagio church just outside Montepulciano. Marvel at the breathtaking Italian Renaissance architecture as your guide points out all the fascinating details that are easy to miss without an expert eye. Last but not least, settle in for the relaxing trip back to Rome as evening falls. You'll be back in the Eternal City with plenty of time to grab dinner.


Roundtrip transport from Rome Tour guide Driver Homemade lunch Wine tasting Local cheese tasting

Important Information

  • Unfortunately, we are unable to accommodate guests with mobility impairments, wheelchairs or strollers on this tour.
  • Please notify us if you have food allergies or other special requirements and we will do our very best to accommodate you.
  • Although the places we visit on this tour accommodate strollers we don't always have enough room in our transport vans to accommodate them. Please notify us after booking if you are traveling with an infant. Also contact us after booking if you require a car seat.

Easy cancellation

Cancel up to 24 hours in advance for a full refund


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