Tuscany Day Trip from Rome with Winery Lunch & Medieval Towns

Go beyond the Eternal City on this Rome to Tuscany day trip.

Tuscany is a can't-miss stop on many visitors' Italian itineraries. But trying to make your way there on your own means spending more time worrying about logistics and less time enjoying yourself. On this Tuscany day trip from Rome, we'll handle all the details, including the itinerary and transportation, so you'll be all set for one of the most memorable experiences of your time in Italy.

Explore ancient Tuscan hill towns, both small and large.

Hop aboard your private bus and enjoy a comfortable and picturesque ride to Val D'Orcia, a region of Tuscany most famous for its impressive landscapes. Surrounded by the rolling green hills and twisting roads lined with cypress trees, it will feel like you're in a scene from the movie "Under the Tuscan Sun".

The first stop on our Tuscany day trip from Rome is the beautiful village of Monticchiello. This tiny town makes for the perfect once-in-a-lifetime photo op to kick off your unforgettable day.

From there, it's off to Pienza, which is bursting with artisanal food, wine, and craft stores. Taste the world-famous pecorino cheese at a small business, see beautiful ceramics, and start to learn about typical Tuscan delicacies and regional products.

Sample the best of Tuscany's famous food at a picturesque winery.

The next stop on your Rome to Tuscany day trip is a local family-run winery in Montepulciano. Stroll through the lush vineyards where the grapes are grown and then step into the breathtaking ancient wine cellar with tall arches like a cathedral. Learn about the winemaking process and how the cellar is engineered to maintain a constant temperature and humidity to age the wine. You'll also sit down to a sumptuous pasta lunch featuring seasonal delicacies and the best of what Tuscany has to offer. (And yes, that includes plenty of the region's incredible wine!)

Marvel at a masterpiece of the Italian Renaissance.

Tuscany is famous for its landscapes and architecture, and you'll experience both as you relish some free time to explore the historic town of Montepulciano on your own. Before heading back to Rome, you'll also stop outside the Temple of San Biagio, a gorgeous Renaissance church nestled among the hills just outside the town that will transport you back to the sixteenth century.

With so much to see in this incredible region, stating that we’ve found the best of Tuscany is a bold claim—but one we’re sure you’ll agree with after a delicious day of medieval villages, wine, food, and stunning landscapes. This Rome to Tuscany day trip offers an essential Italian experience that will leave you craving Tuscany long after you’ve returned home.

Please note that this description is an example and your experience may vary depending on the season, day of the week, and group size. Regardless of where your tour goes, you always have an excellent experience.