Chianti wine, Siena and San Gimignano in one day from Florence
One tour on our list trades extra wineries for two famous hill towns. Gray Line Florence fills about 11 hours with San Gimignano, a Chianti estate lunch and Siena, which suits a first trip to Tuscany better than a wine enthusiast. These are the stops, the options and the catches.
One coach, four stops, about 11 hours
Gray Line Florence runs the only tour of our five that adds towns to the wine. Its coach day lasts about 11 hours from Piazzale Montelungo, with San Gimignano, a Chianti winery with lunch, Siena and, outside winter, Monteriggioni. The order of stops may vary on the day.
It is sold on GetYourGuide only, from ~$79 per person, which the listing shows as a sale price. It scores 4.6 from 4,400+ reviews, a solid result for a coach day this long.
The coach leaves from beside Santa Maria Novella station, the same area our pick uses. Directions and luggage rules for both meeting points are in our meeting point guide.
San Gimignano and its towers
San Gimignano is the hilltop town known for its medieval towers. The tour gives you about two hours of free time there, enough to walk its lanes, find a view over the valley and sit down for a coffee.
Free time means no guide, which suits people who like to wander at their own pace. Those who want someone explaining what they see should look at the Siena part of the day and the option they book.
Two hours goes quickly in a town this popular, and the lanes near the main gates fill up with other coach groups. Walking a few streets away from the busiest square usually buys a quieter view and an easier table.
The winery stop and the lunch
The wine part of the day is a single Chianti estate. You tour the vineyard and the cellar, taste three Chianti wines and then sit down to a three-course lunch, with cantucci, the hard almond biscuits, to finish.
The sample menu on the listing opens with cured meats and bruschetta beside pecorino with balsamic. Penne with a meat ragù follows, then a jam tart served with a sweet wine. If you follow a special diet, ask the operator before booking.
Chianti and Chianti Classico are both poured with lunch. What separates the two, and why the black rooster matters, is explained in our guide to what is in your glass.
The tasting pours are small rather than full glasses, and leaving some behind is normal. With a coach doing the driving nobody has to stay sober, though an afternoon of uphill walking in Siena is a good reason to go gently.
Siena, and what your option includes
Siena is the larger of the two towns, built around the shell-shaped Piazza del Campo and its striped cathedral. The listing ties the guided walk and the cathedral visit to the option you select, so read the option text rather than the headline.
If the cathedral and its Piccolomini Library are the reason you go, make sure the option you pay for names them. Both towns involve uphill streets and old paving, which matters for anyone who finds hills hard.
Monteriggioni, outside winter
Monteriggioni is a small walled village on a hilltop north of Siena, and the tour treats it as a short stop on the way. It is included in season only.
From November to March the village is dropped, and the day ends about 30 minutes earlier. If the walls of Monteriggioni are on your list, a date from spring to autumn is the one to book, and our seasons guide covers the weather in those months.
Who this day suits, and who should pick a wine tour
This is a sightseeing day with wine in it, not a wine tour with sightseeing. You get one winery with three tasting wines and lunch, against six wines and olive oils across two estates on Prestige Rent's small-group tour from ~$101.
It suits a first visit to Tuscany with one free day, when the towns matter as much as the cellars. It also suits travelers who would rather not work out public transport between Siena and San Gimignano themselves.
It works less well for anyone who wants long conversations with a winemaker or a second estate to compare. One cellar visit in a group of up to 50 gives a taste of Chianti, not a close look at it.
If wine is the point, the Towns of Italy trail from ~$99 visits three wineries plus an olive oil mill, with a stop in Greve in Chianti and a smaller group. Our half-day or full-day guide compares the lengths side by side.
Two hill towns and a winery lunch by coach
Gray Line Florence covers San Gimignano and Siena with a Chianti estate lunch between them. Pick the option that includes the Siena walk if you want a guide in town.
Similar days by other companies exist on Viator, with their own stops and prices. We compare this one because its winery visit and lunch are spelled out clearly on the listing.
The catches of a long coach day
- About 11 hours, much of it on a coach of up to 50 people
- Wine is one stop of four, with three tasting pours plus wine at lunch
- Not suitable for wheelchair users, with uphill walking in both towns
- The listing charges €80 if you lose the audio guide
- Monteriggioni is skipped from November to March
Bring comfortable shoes and a layer, since the walking is uphill and the paving uneven. A coach of 50 feels different from a minibus of 8, a gap our minibus or coach comparison sets out.