Florence: Chianti Wine Tasting & Montalcino Day Trip

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Guide in English or Italian08:30

Guide in English or Italian08:30

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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.

Step-by-step itinerary

Tuscany medieval villages and wine tasting

• 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.

Days and timesTue · Thu · Sun · 08:30

AgesAges 9+ · 3 to 8 years · Under 3

Meeting point and pickupNo pickup · ends where it startsMeeting point, per the operator: “in front of Caffe' Gilli at 08:25am”

Cancellation and refundsFree cancellation up to 24h before the start. After that, no refund.It may be canceled if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated today

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.

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Top questions

What languages is the guide in?

Live guide in English and Italian.

Can children come?

3 to 8 years; under 3.

How long is the tour?

Approximately 7–8 hours from pickup to drop-off, including driving time between stops and time to walk through the villages.

What wines do you taste?

In Chianti, you taste Chianti wine, vin santo, and try extra virgin olive oil. At the farmhouse lunch near Montalcino, you taste Rosso di Montalcino, Brunello, and Supertuscan wines paired with food.

Is lunch included?

Yes. A guided 2-course lunch at a historic farmhouse with wine pairings and local products like cheese, cured meats, and homemade biscuits is included.

How many people are in the group?

Small groups of up to 8 people maximum.

Does the driver provide historical information in the villages?

The driver gives general introductory information during the drive and points out landmarks, but cannot lead formal guided visits inside towns or provide detailed historical and artistic commentary. You explore the villages on your own during the stops.

Is hotel pickup included?

Yes, if your hotel is in central Florence. Pickup and drop-off at your Florence City Center hotel are included.

What should I wear?

Comfortable walking shoes are recommended, as you'll be walking through villages on steep streets. Appropriate clothing is suggested if you visit any churches.

Is the minivan air-conditioned?

Yes, the minivan is air-conditioned and has WiFi on board.