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Florence: Chianti Wine Tasting & Montalcino Day Trip

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Free cancellationExcellent quality

1/14

Duration10h

GroupUp to 8

LanguagesEN · IT

Mobile ticketAccepted

Rolling vineyards, three medieval villages, and lunch at a working Tuscan farm

You're picked up from your Florence hotel and driven through Chianti vineyards for a morning wine and oil tasting, then to a working farmhouse near Montalcino for a guided lunch with local wines and regional food, followed by walks through the medieval villages of Montalcino and Montepulciano, with return to Florence by evening. The minivan holds eight people maximum and includes WiFi, so you're not crammed in, and the driver handles all the navigation and timing.

10h

Step-by-step itinerary

Travel through Tuscany countryside
Taste Chianti wines and local products
Admire Monteriggioni village
View Crete Senesi clay landscape
Explore Val d'Orcia UNESCO site
Enjoy guided lunch and wine tasting
Visit Montalcino medieval village
Walk Montepulciano fortified town
Taste wine in Montepulciano cellar

The Experience

The minivan picks you up in central Florence and heads south into the Chianti hills before most tourists are awake. You're in a small group—no more than eight people—and the driver speaks English, though he'll stay in the minivan when you're walking through the villages; he's there to get you between places and point out what's coming, not to narrate the history. The first stop is a working vineyard in Chianti where you taste several wines—Chianti itself, plus vin santo with local cantuccini biscuits, and extra virgin olive oil on Tuscan bread. It's a real tasting, not a shop, and you're standing in the vines while someone explains what you're drinking.

After that, the drive gets scenic in a way that doesn't photograph well but stays with you. You pass Monteriggioni, a medieval village so small and intact it looks like a toy, then drop into the Crete Senesi—a landscape of bare clay hills that feels like another planet, then climb back up into the Val d'Orcia, which is a UNESCO World Heritage site and looks like every Tuscan postcard you've ever seen, except you're actually there. The road winds through cypress-lined valleys and past old stone farmhouses. Around midday you arrive at a historic farmhouse near Montalcino where lunch happens. It's a guided tasting: two courses, wines from the Montalcino region (Rosso di Montalcino, Brunello, Supertuscan), local cheeses and cured meats, homemade desserts. After lunch there's time to walk the cellars or just sit in the garden.

Then you're back in the minivan for the village stops. Montalcino sits on a ridge with a fourteenth-century fortress at the top—the view down into Val d'Orcia from up there is the reason people come. The streets are narrow and steep, lined with wine shops and small artisan places. You get an hour or so to walk around, buy a bottle if you want, or just stand in a piazza. Montepulciano comes last, perched at 600 meters on a hill between two valleys, with Renaissance buildings and more wine cellars tucked into the old town. The driver drops you back at your Florence hotel in the evening. The whole day is about seven or eight hours, and you're moving between places the whole time, but it doesn't feel rushed because the stops are short and the driving is part of the experience—you see the landscape change as you go.

What’s included

Hotel pickup and drop-off in central Florence.
guided Chianti wine and olive oil tasting.
2-course lunch with wine pairings at a historic farmhouse near Montalcino.
visits to the medieval villages of Montalcino and Montepulciano with free time to explore.
transport by air-conditioned minivan with WiFi and English-speaking driver.
small group of up to 8 people.

Good to know

Easy physical levelInfant seats availablePublic transport nearby

Operated by CAF Tour and Travel - Gray Line Florence

Is this one for you?Best for travelers based in Florence who want to see the main Tuscan wine villages and taste wines at source without renting a car or arranging their own transport and timing—the fixed schedule and included lunch mean you show up at your hotel and the rest is handled.