Chianti Wine Tasting & Sunset Tour from Florence

Two Wineries & Tuscan Sunset: The Chianti Tour That Skips the City Heat

You spend an afternoon driving through Chianti's vineyard landscape, stopping at two family-run wineries for tastings paired with Tuscan food, visiting hilltop villages like Greve in Chianti and Montefioralle, and watching the sunset from the countryside instead of the city. Hotel pickup is included if you book the private option, and the group stays small — maximum eight people — so the pace feels personal rather than herded.

Step-by-step itinerary

Chianti wine tour and sunset visit

• Depart Florence for Chianti countryside
• Drive through vineyards and hilltop villages
• Visit first family-run winery
• Enjoy wine tasting with Tuscan food
• Visit second winery for tasting
• Stop for photos of landscapes
• Experience sunset over Chianti region
• Return to Florence

The Experience

Our driver pulled up to the hotel right on time, and within twenty minutes we were past the last ring of Florence traffic and into rolling vineyard country. The minivan was cool and comfortable — important, because it was still hot in the city — and he knew exactly where the light would be best later. That's the thing about doing this in the late afternoon: you're not fighting crowds at the wineries, and you're not sitting in a restaurant watching the sunset through a window. You're actually in it, standing in the vines while the sky changes color.

The first winery was a family operation that's been making Chianti Classico for generations. The owner walked us through the vineyard, pointing out the difference between the older vines and the newer plantings, and then we tasted two wines — the Classico and a Super Tuscan they're proud of — paired with local cheese, cured meat, and bread. It wasn't a formal sit-down; it was standing around a wooden table with a view of the hills, and the owner's English was good enough that you didn't feel like you were missing anything. After that, we stopped in Greve in Chianti, a small hilltop village where you could actually walk around without bumping into tour groups, and then moved on to the second estate for another tasting and a proper look at the landscape as the light started to shift.

By the time we reached the second winery, the sun was lower and the whole valley had turned golden. The driver had timed it so we weren't rushed — you had maybe an hour to sit with the wine, eat some more food, and just be there while the light did what it does. No one was pushing you back to the minivan. The villages we passed through — Montefioralle, Badia a Passignano — felt like actual places where people lived, not sets. And yeah, the driver stopped whenever someone wanted to take a photo, which meant you got the shots that actually look like what you saw, not the ones everyone else got from the same marked viewpoint.

If you want dinner after the tastings, that's available through a separate option, but most people skip it — you've already eaten well, and by then you're ready to head back to Florence. The whole thing is five hours door-to-door, which means you're not losing your whole evening, and you're not doing the rushed version where you hit three places in four hours and taste wine like you're checking boxes.

What’s included

• Your day includes hotel pickup (if private option selected), an expert English-speaking driver, comfortable air-conditioned minivan transport for up to eight people, visits to two family-run wine estates, tastings of Chianti Classico and Super Tuscan wines, typical Italian appetizers paired with the tastings, a tour of the vineyards, and stops in hilltop villages like Greve in Chianti, Montefioralle, and Badia a Passignano.
• Dinner at a restaurant is available as an additional paid option.
• The driver will stop for photos whenever you want them.

Good to know

Easy physical levelWheelchair accessibleAccessible transportStroller friendlyInfant seats availablePublic transport nearbyInfants must sit on laps

Operated by ACCORD Italy Smart Tours & Experiences

Is this one for you?Book this if you want to taste real Chianti at the source without spending a full day on logistics — the fixed five-hour schedule, included transport, and two confirmed winery visits mean you're not arranging anything yourself, and the late-afternoon timing lets you catch the sunset light that makes the landscape worth seeing in the first place.

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Top questions

How long is the tour?

Five hours total, including drive time from Florence and both winery visits.

What wines do you taste?

Chianti Classico and a Super Tuscan wine from the family-run estates you visit.

Is food included?

Yes. Typical Italian appetizers and local cheese, cured meat, and bread are paired with the wine tastings at both wineries. Dinner at a restaurant is available as a separate paid option.

What's the group size?

Maximum eight people per minivan, which keeps the experience more personalized than larger tours.

Is hotel pickup included?

Hotel pickup is available if you select the private option. Contact the operator with your accommodation address to confirm.

Can I bring children?

Yes. Children can join if accompanied by two paying adults. Specialized infant seats and strollers are available.

Is the tour wheelchair accessible?

Yes, the minivan and winery visits are wheelchair accessible, and transportation options are available for those with mobility needs.

What time does the tour start?

The tour departs in the late afternoon to catch the sunset. Exact pickup time depends on your hotel location and the season.

What if the wineries aren't available?

The itinerary may change based on winery availability, but the driver will ensure you visit two estates and complete the full Chianti experience.

Do I need to speak Italian?

No. Your driver is an English-speaking expert, and the winery owners speak enough English to guide you through the tastings and vineyard tour.