Tuscany: Private Wine Tour Chianti Classico & Food Pairing

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Free cancellationExcellent quality

1/16

Duration8h

GroupPrivate

LanguagesEN · IT

PickupAt your hotel

Chianti hills, family-run wineries and food pairings in Tuscany

You’ll meet Tuscan winemakers in their own cellars, taste Chianti Classico and Supertuscan wines straight from the source, enjoy a private lunch with local food pairings, and travel through rolling hills with your sommelier guide—leaving you with memories of laughter, real stories, and flavors that linger long after you’re back home.

Step-by-step itinerary

Private Tuscany Wine Tour and Tastings

Drive through historical downtown
Scenic drives with stunning views
Stop time permitting
Enjoy steep vineyards and olive groves
Visit three selected wineries
Wine tasting including Supertuscan wines
Olive oil and balsamic tasting
Food and wine pairing lunch

The Experience

We’d barely stepped out of the minivan in Chianti when Paolo—the owner at our first stop—waved us over like we were old friends. I tried to say “buongiorno” with my best Italian accent (he grinned politely). The air smelled like wet earth and rosemary. Paolo poured the first glass of Chianti Classico before we’d even finished introductions. He told us his grandfather planted these vines. I could see him watching our faces as we tasted—like he was hoping we’d get it. I think I did.

The drive between wineries was all winding roads and olive trees, sunlight flickering through the window. Our guide, Elena, knew every twist—she pointed out a medieval tower on a hilltop and laughed about how she still gets lost sometimes. At the second winery, the cellar was cool and dark, stone walls dripping with history (and probably humidity). Tasting their Supertuscan felt almost ceremonial—so much going on in one sip that I just had to sit for a second. Lunch came next: homemade pici pasta with wild boar ragu, paired with something bold and red. I tried not to eat too fast but honestly failed.

I didn’t expect to talk so much with the winemakers themselves—they really did pour the wine themselves, telling stories about each bottle. The olive oil was grassy and sharp; I dipped bread into it while listening to Elena translate a joke about local politics that went right over my head but made everyone else laugh. There was balsamic too, thick as syrup. By the last stop, my notes were a mess of scribbles (“try this again?”) and little hearts next to favorites.

The whole day felt less like a tour and more like being invited into someone’s routine—except their routine involves pouring you generous glasses of wine in Tuscany’s most beautiful corners. It’s hard not to feel a little spoiled by it all. Even now I can remember how quiet those vineyards felt for a moment after lunch, just cicadas buzzing somewhere close by.

What’s included

Your day includes hotel pickup and drop-off by comfortable minivan, all tasting fees at three family-run Tuscan wineries (with plenty of Chianti Classico and Supertuscan), extra virgin olive oil tastings—and a full lunch featuring local food paired with wines before heading back home together in the evening.

Good to know

Easy physical levelPublic transport nearbyNot for pregnant travelers

Operated by Cooltours