Tuscany Day Trip: Siena, Cortona & Montepulciano with Wine Tasting

Summary

Small group journey through Siena, Cortona and Montepulciano with farm lunch and wine

You’ll walk medieval streets in Cortona, taste fresh farm food under Tuscan sun, sip wine deep inside Montepulciano’s ancient cellars, and end your day wandering Siena’s glowing piazzas—all with stories from your local guide and time to just soak it in.

What’s the experience like?

We’d barely left Florence when our guide, Marco, started telling stories about the hills outside the van window—he even pointed out a row of cypress trees that looked straight out of a postcard (or maybe a movie, I guess). First stop was Cortona. The old stone streets really do twist and climb just like in “Under the Tuscan Sun”—I got lost twice and ended up buying a tiny jar of honey from a woman who smiled but didn’t say much. The air smelled like coffee and something sweet baking. I tried to say “grazie” with the right accent; she laughed anyway.

After Cortona, we rolled into this little farm where Cinta Senese pigs were snuffling around under olive trees. I’m not usually into farm tours but honestly—fresh bruschetta with tomatoes still warm from the sun? That’s something I still think about. We sat outside for lunch, tasting their own wine (stronger than I expected) while Marco explained how these hills show up in movies like “The English Patient.” There was this quiet moment when everyone just looked at the view instead of talking. It felt good.

Montepulciano came next—a walled town that looks almost too perfect from a distance. We had time to wander before meeting at an underground cellar for a proper wine tasting (the Nobile di Montepulciano is as earthy as they say). Someone in our group tried to find the spot from “Twilight,” but I was more interested in the cheese samples. The drive through Val d’Orcia after that was all golden fields and those skinny trees you see on postcards—at some point, I stopped taking photos because it felt better to just watch.

Siena was our last stop. By then my legs were tired but walking into Piazza del Campo as the sun slid down behind the rooftops made me forget it for a minute. Marco led us through backstreets full of chatter and laundry lines before letting us loose for an hour—enough time for an espresso and some people-watching by Palazzo Pubblico. The ride back to Florence was quiet, except for someone quietly humming an old Italian song near the window.

Step-by-step itinerary

Day 1 — Tuscan towns and wine tasting tour

• Meet tour leader at Porta Romana, Florence
• Travel 1.5 hours through Tuscan countryside
• Explore hilltop town of Cortona independently
• Visit local farm for tasting and stroll
• Travel 40 minutes to Montepulciano
• Explore Montepulciano and taste local wines
• Drive through Val d'Orcia and relax
• Visit medieval town of Siena and explore
• Return to Florence by 8:00pm

Top questions

How long is the Tuscany day trip from Florence?

The tour starts at 8:00am by Porta Romana in Florence and returns around 8:00pm—about 12 hours total including travel between towns.

Is lunch included on this Siena & Montepulciano tour?

Yes, there’s a farm lunch with local products like cured meats, bruschetta made from garden ingredients, and their own wine.

Are wine tastings part of this small group Tuscany tour?

Yes, you’ll have complimentary tastings at both a local farm and an underground cellar in Montepulciano.

How much free time do we get in each town?

You’ll have independent time to explore Cortona, Montepulciano, and Siena during stops—usually about an hour or more per town.

Does this tour include Val d’Orcia?

Yes, you’ll drive through Val d’Orcia after Montepulciano with time to enjoy its iconic landscapes from the comfort of your van.

Where does the tour start?

The meeting point is Porta Romana in central Florence at 7:45am for an 8:00am departure.

Is hotel pickup included?

No hotel pickup; you meet your guide at Porta Romana in Florence.

What kind of vehicle is used for this Tuscany day trip?

A comfortable private minivan with eight seats is used for transport between towns.

Are there any health or fitness restrictions?

This tour isn’t recommended for pregnant travelers or those with poor cardiovascular health or walking disabilities; moderate fitness is needed due to hilly towns.

What’s included

Your day includes travel by comfortable eight-seat minivan starting from Florence’s Porta Romana, guided stories along the way, stops at Cortona, Montepulciano (with entry to a 14th-century cellar for complimentary wine and cheese tastings), lunch at a local farm featuring their own products and wines among olive groves, free time to explore Siena’s medieval center and main piazza before returning to Florence by evening.