Tuscany Day Trip From Rome: Wine & Medieval Towns

Experience Tuscany’s medieval towns and vineyard lunch on a small group day trip

• Get off the beaten path in the medieval villages of Tuscany.
• Sit down to a traditional, homemade Tuscan lunch.
• 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.

Awaken all your senses on this magical day trip, which whisks you away from the busy streets of Rome and out to the tranquil medieval towns and verdant vineyards of the Tuscan countryside. From the storied cobblestone streets of Pienza (a UNESCO World Heritage site) to an ancient wine cellar in Montepulciano and beyond, this perfectly planned day trip will immerse you in one of Italy's most enchanting regions. With all transportation and logistics handled, all you have to do is show up ready to eat, drink, and explore. 

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. 

• Fortress of Montalcino, Via Ricasoli, Montalcino, Province of Siena, Italy
• Tuscany, Italy
• Val d'Orcia S.r.l., Via Dante Alighieri, San Quirico d'Orcia, Province of Siena, Italy
• Pienza, Province of Siena, Italy

Before you travel, please read the "Know Before You Go" section for essential information, requirements, and possible disruptions regarding your tour.