myTour in Italy · Siena
A minivan from Siena railway station climbs to Castellina in Chianti, then stops at two wineries for tastings and ends at the walls of Monteriggioni. If you're sleeping in Siena, it's the shortest and cheapest way into the hills.
Siena sits just south of the Chianti Classico zone, so you're in the hills fast. The tour leaves from the railway station and goes first to Castellina in Chianti for 45 minutes in the village. Then come the two tastings. Fattoria Lornano is an old family estate on the border of Castellina and Monteriggioni and a founding member of the Gallo Nero consortium; its Chianti Classico is 100% Sangiovese. Agricola Poggio ai Laghi faces the castle of Monteriggioni and makes Chianti, Chianti Riserva and Super Tuscans: good wine, but not Classico. A last half hour at Monteriggioni closes the loop.
Reviewers mostly describe an afternoon departure, and they like it: "two very complete wine tastings", a guide with humour, a good group. One April 2026 guest felt the wineries pushed sales, and the second was "much more expensive" than the first. Another found the second tasting rushed.
The one real warning is from May 2026: a tour was cancelled at short notice and the operator sent the message by WhatsApp only, so the guests stood at the bus terminal waiting. Give a mobile number that has WhatsApp when you book, and check it the day before. With just 11 reviews and $56 per person, it's still the obvious pick from Siena; the Fiat 500 day is the other option nearby.
Meet the team at Stazione di Siena. Keep your phone on: the operator uses WhatsApp.
A walk through the hill village and its church square.
Cellar and a Chianti Classico tasting at the family estate.
A second tasting facing Monteriggioni's castle.
Time inside the walled village before the drive back to the station.
★★★★★Our tour guide Val and Massimo the driver were excellent. Val spoke fluent English, her knowledge and humour made the experience fun. The wine tasting was lovely too, we had time to explore and take many photos. Very good value and would highly recommend.
★★★★★This was a great way to see the countryside and enjoy two beautiful vineyards. We really liked both vineyards and learned quite a bit about wine.
★★★★★Very entertaining afternoon with two very complete wine tastings and beautiful landscapes and towns. Additionally, Balesca, our guide, was delightful.
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At Siena railway station (Stazione di Siena), and it ends there too. There's no hotel pickup.
Fattoria Lornano, a Chianti Classico estate on the edge of Castellina, and Agricola Poggio ai Laghi near Monteriggioni, which makes Chianti and Super Tuscans. Both include a tasting.
Reviewers describe an afternoon. Departure times can change by season, so check the time on your booking.
About five hours: 45 minutes in Castellina, 1.5 hours and 1.25 hours at the two wineries, and 30 minutes in Monteriggioni, plus the driving.
Ready to book
Castellina in Chianti and two wineries in half a day, meeting at Siena railway station.
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
Vintage Fiat 500 Tour with Lunch & WineYou drive a 1960s Fiat 500 in convoy to Monteriggioni and a Castellina winery for lunch and two wines.★ 4.3 · 7 hours · from $170
Greve in Chianti Winery Tour & TastingAlready in Chianti? A small family estate above Greve, about four Classico wines with cheese and salami.★ 4.7 · 1.5 hours · from $57