Towns of Italy · Florence
A minibus takes you from the Arno to three wineries and an olive oil mill, with a three-course Tuscan lunch in the middle of the day. It's the trip for people who want the most tasting per hour, and who don't mind a first pour at a quarter past ten.
Towns of Italy runs this from the same corner by the Arno as its Vespa tour. The day has four stops in the countryside: two wineries in the morning (the operator describes a famous one with a big cellar and a small boutique estate), an olive oil mill on an old estate, and a long lunch of three courses with wine. A third winery closes the afternoon. Reviewers praise the guides by name, and it shows in the 4.9 rating.
The estates aren't listed, and the operator's own description promises both Chianti and Chianti Classico wines. If the black rooster matters, ask which estates are on your date. One April 2026 guest wished for more olive oil than they got; the mill is a visit and a tasting, not a class.
Watch the group size. The standard option takes up to 20 people. A guest in October 2025 expected a Mercedes van of eight and got a bigger group, because only the semi-private Super Tuscan upgrade caps the group at eight. Another found the minibus seats cramped. At $122 it's still good value for three wineries and lunch, and we'd book it over two coach tours. From 1 March 2027 the meeting point moves to Largo Pietro Annigoni 9A.
At the corner of Piazza Mentana, opposite the Arno. From 1 March 2027: Largo Pietro Annigoni 9A.
A cellar tour and the first tasting, usually around 10:15.
A different style of estate and a second tasting.
How the oil is pressed and how to taste it.
A three-course Tuscan meal with wine and a final tasting.
Drop-off at the meeting point.
★★★★★Great trip. Definitely worth the time and money. Beautiful vineyards, photo ops and great staff at each vineyard. FYI…..you start sipping wine at 10:15 am, if you’re ok with that
★★★★★Not as much olive oil as I was hoping. Well worth the time. Pace yourself!! Visited 3 wineries. One newer one and a couple older. Nothing was rushed but didn't drag either. Enough time to appreciate each stop.
★★★★★We started in the morning and drove to a beautiful winery. After that, we were treated to an amazing lunch and wine pairing. We ended the day with a tour of a winery and olive oil farm.
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Three, plus an olive oil mill. Lunch, three courses with wine, is served at one of the stops.
The standard option takes up to 20 people in a minibus. Only the semi-private upgrade, with a certified wine expert and Super Tuscan wines, is capped at eight.
Yes. Italian law forbids serving alcohol to under-18s, so they get non-alcoholic drinks at the tastings. Infants ride on a lap.
Some may be. The operator promises Chianti and Chianti Classico wines but doesn't name the estates. Ask on the day, or read our Chianti vs Classico guide to spot the black rooster seal.
Ready to book
Three wineries, an olive oil mill and a three-course Tuscan lunch in one day from Florence.
Semi-Private Chianti & San Gimignano DayEight seats at most: San Gimignano early, a winery lunch with its wines, then a second estate and hotel drop-off.★ 4.9 · 8.5 hours · from $237
Small-Group Chianti Classico Half DayTwo Classico wineries on the Chiantigiana, up to seven wines and olive oil, eight guests at most.★ 5.0 · 5 hours · from $170
Half-Day Chianti Tasting at Two WineriesThe most-booked Chianti tasting from Florence: two wineries, about eight wines with food, back by evening.★ 4.5 · 5.5 hours · from $62