Ciao Florence Tours · Florence
A long coach day from Florence to Monteriggioni, Siena and San Gimignano, with one wine estate at the end. Pick it for the towns: it's the cheapest way to see Siena with a guide, and the tasting is a bonus rather than the point.

Be honest with yourself about what you want. This is a sightseeing day with a glass at the end. You get about an hour inside the walls of Monteriggioni, three hours in Siena (a guided walk with headsets from Piazza del Campo to the cathedral, then free time), an hour in San Gimignano, and finally one winery with two or three wines and snacks in the hills outside town. One of the operator's own photos shows the cellar shop at Agricola Poggio ai Laghi near Monteriggioni. Neither area is in the Chianti Classico zone.
Two costs aren't in the price: lunch, and the Siena cathedral ticket (the listing says about EUR 7). The guide offers a group lunch at a set restaurant in Siena. Guests are split on it; some loved the pasta, others say take the time and find your own place on the side streets.
With 3,600 reviews and a 4.7 rating, it runs well for what it is. The complaints are about scale: groups of 50 to 70, headsets that fail, a guide switching between three languages, and a winery stop that some call a sales pitch. If wine is your reason for going, the semi-private day with San Gimignano keeps the town and gives you two wineries and a long lunch.
The tours and news kiosk at the bus terminal, 5 to 10 minutes on foot from Santa Maria Novella. Staff wear fuchsia Ciao Florence jackets.
Free time in the walled hamlet. Guests report anything from 30 minutes to an hour. Walking the wall costs extra.
A guided walk with headsets from Piazza del Campo to the Duomo, then free time and the optional group lunch.
Free time to wander the towers. Gelateria Dondoli, on the main square, is a listed stop.
Two or three Chianti wines with snacks in the hills outside San Gimignano, and a shop.
Drop-off at Piazzale Montelungo, about 10.5 hours after you left.
★★★★★Combining Sienna, San Gimignano and Monteriggione into one day provides plenty to see and do without spending so much time on a bus. They provided the option for a group lunch at a prearranged restaurant. It was one of the best pasta dishes of our 7 days in Tuscany.
★★★★★It’s a long day but totally worth it! We were a large group of over 70 people and while I did feel a little silly following our guide in Siena wearing headphones I found the tour to be very interesting and helpful information for understanding the city better.
★★★★★It was nice to arrive at our first hill town early, before other tour buses got there, as it is a very small town. [...] I’ve read other reviews that found the winery their tour visited was disappointing. Our winery stop was very good.
★★★★★Not for anyone with mobility issues as the bus parks some way from each centre and there are a good few steps to negotiate. Wine tasting was a good laugh. An appropriate amount of time at each stop.
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No. You can join a group lunch at a set restaurant in Siena and pay there, or eat on your own. The only food in the price is the snack plate at the winery.
About an hour at one estate, with two or three Chianti wines and snacks. One guest timed it at 50 minutes. It is the last stop before the coach back to Florence.
Only if you buy a ticket during free time. The guided walk ends at the Duomo, and the listing puts the ticket at about EUR 7. Tickets are sold on the official Opera del Duomo site.
No. Siena, San Gimignano and Monteriggioni all sit outside the Classico zone, and so does the winery. If you want Gallo Nero estates, look at the Classico half day.
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A guided walk in Siena, free time in San Gimignano and Monteriggioni, and a Chianti estate with two or three wines.
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