CAF Tour & Travel (Gray Line Florence) · Florence
A coach takes you out of Florence along the Chiantigiana road to two wineries, where the owners or their staff pour three or four wines each with cheese, salami and bruschetta. Pick it if you want a real taste of Chianti and still have your evening back in town.
This is the big one: more than 4,700 reviews and a coach of up to 50 people. It leaves from Piazzale Montelungo, at the end of the ramp beside Santa Maria Novella station, and follows the SR222 Chiantigiana south. The first stop is a small organic estate near Greve, where the owner talks you through the house wines with local food. Then the coach carries on toward Siena for the second, a family winery with a cellar, an aromatic garden and at least four wines poured at the table.
Expect about eight wines in all, plus olive oil and balsamic vinegar. One guest counted exactly that. The food is a tasting plate, not lunch, and several reviewers say eat before you go. The listing calls the second estate "Sienese Chianti Classico"; its map pin is Monteriggioni, and a 2024 guest named it as Agricola Poggio ai Laghi, which makes Chianti and Chianti Riserva rather than Classico. If the black rooster matters to you, our Chianti vs Chianti Classico guide explains why.
Reviews split along one line: guests love the second winery and shrug at the first. In September and October 2026 several people called the first stop disappointing; one wrote that every wine went into the same glass. Two July 2026 reviewers also report a coach with broken air conditioning on a hot day. At $62 (on sale at $53 until 31 October 2026) it's still the cheapest guided way to taste at two estates, and for a first look at Chianti we'd book it. Want fewer people and more pours? The 8-seat Classico half day costs more and feels like a different trip.
At the end of the ramp from Santa Maria Novella station. Staff wear blue with CAF Tour - Gray Line logos. Bring your original ID: the listing asks for it.
Out through the olive groves and vineyards on the SR222, with commentary from the tour leader.
A small organic estate: a short talk on how they make their wine, then a tasting with local products.
A walk up through the vines to the cellar, then four or more wines, olive oil and balsamic at a long table. The road up is steep.
The coach drops you where you started, at Piazzale Montelungo.
★★★★★The bus trip TO the wineries is a valuable part of the trip! Put your phone away and gaze out the window, imagining the hundreds of years farmers harvested and artists captures the warm sunlight on the rolling hills. The wineries were charming and the tastings expertly hosted [...]
★★★★★The first winery is a small family run business, offering a selection of their locally grown tasters, and the second a slightly larger business with a generous selection of wine, oils and traditional food. [...] Great value and would definitely recommend!
★★★★★The actual wine tasting along with the food was just outstanding. Make sure to wear comfortable shoes and be prepared for a steep walk up to the entrance of the second vineyard.
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Three or four at each of the two wineries, so about eight, plus olive oil and balsamic vinegar. Some hosts pour more generously than others; one guest at the second estate counted four or five full glasses.
No. You get cheese, cured meats and bruschetta with the wines. Lunch is only included if you book the cooking class option, which adds a class and a meal with four wines.
One of them. The first stop is near Greve, inside the Classico zone. The second sits near Monteriggioni, just outside it, and makes Chianti and Chianti Riserva. Wineries can change, so ask your guide which ones you're visiting.
At Piazzale Montelungo, at the end of the ramp beside Santa Maria Novella station. Look for staff in blue clothing with CAF Tour - Gray Line logos. There's no hotel pickup.
Ready to book
Two family wineries on the Chiantigiana road, three or four wines at each with local food, coach from Florence. Free cancellation up to 24 hours before.
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
Siena, San Gimignano & a Chianti WineryA big coach day: Monteriggioni, a guided Siena walk, San Gimignano, then one winery with two or three wines.★ 4.7 · 10.5 hours · from $74
Chianti Half Day from SienaFrom Siena station: Castellina in Chianti, two winery tastings and the walls of Monteriggioni in an afternoon.★ 4.5 · 5 hours · from $56