Quintessential Tuscany: Wine Tasting and Hilltowns from Rome

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.

After a comfortable ride via private transport, the first stop on our Tuscany day trip from Rome is the picturesque town of Pienza, which is bursting with artisanal food, wine, and craft stores. Taste the world-famous pecorino cheese along with other regional products at a small business, see beautiful ceramics, and start to learn about typical Tuscan delicacies like wild boar ragu. You'll have a bit of free time to spend at your leisure, but we recommend visiting the town’s church and soaking up some more views over the rolling hills of Val d’Orcia.

Sample the best of Tuscany's famous food on a picturesque farm.

Don't eat too much in Pienza, though—the next stop on your Rome to Tuscany day trip is a local farm for a sumptuous lunch. Take a brief stroll to see what is growing or being raised that season before sitting down for a farm-to-table lunch featuring seasonal delicacies and the best of what Tuscany has to offer. Because the menu changes according to what's in season, we can't guarantee the specific dishes in advance—but rest assured that you are going to enjoy a proper Tuscan feast!

Climb the walls of a medieval castle for stunning views over Tuscany.

Tuscany is famous for its castles, and your next stop is one of the best. Perched high on top of a hill, Montalcino Castle offers perhaps the best views in Tuscany. With special access, you’ll climb the lookout towers and patrol the castle walls with your Walks tour leader to show you the way.

Enjoy world-famous wines right at the source in Montalcino.

One crucial part of your Tuscan experience awaits: the wine! Tuscany is world-famous for its wines, and none is more renowned than Brunello di Montalcino. Sample some of the best at an award-winning vineyard for a guided tour of the vines and wine cellar, plus a guided tasting flight. Go on—we dare you to leave without a bottle or two stashed in your bag.

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 castles, wine, cheese, and perfect hill towns. Our Rome to Tuscany day trip offers a truly Italian experience that will leave you craving Tuscany long after you’ve returned home.