The best time to book a Tuscany wine tour from Florence
Wine tours leave Florence for the Chianti hills through the whole year, so there is no closed season to dodge. What changes is the color of the vines and the heat on the road, and with them how full the tasting rooms get. This page is our opinion, not a promise from any operator.
The year in the Chianti hills, side by side
None of the tours on this site closes for winter, and the two we read most closely say they run rain or shine. So the question is less whether you can go and more which version of the countryside you want to see.
| Time of year | In the vineyards | What we think |
|---|---|---|
| April to June | Fresh green leaves, mild days | Our first choice for comfort and color |
| July and August | Full canopy, grapes ripening | Hot and busy; take a short tour |
| September to early October | Harvest, picking and pressing | The liveliest weeks; book ahead |
| Late October | Leaves turning, harvest mostly done | A calm, pretty shoulder |
| November to March | Bare vines, cellars still open | Quiet and cold; fine if wine is the point |
Harvest weeks, from September into early October
The grape harvest, the vendemmia, usually falls somewhere around September and runs into early October. The exact days shift with the weather of each year and with each estate, so nobody can promise you a picking day in advance.
When it lines up, the estates feel busy and alive. Tractors move between the rows while crates of grapes come in, and the smell of crushed fruit hangs around the cellar doors. Hosts are often in a good mood, if a little stretched.
The downside is that everyone else wants these weeks too. Small groups fill early, and the winery staff have their own harvest work to do. You taste the same bottles as in any other month, since this year's grapes are nowhere near ready to drink.
Spring, when the vines turn green
From April to June the hills are at their freshest. New leaves cover the vines and the grass between the rows, and days are usually mild enough to stand in a vineyard without hunting for shade.
For most visitors this is our favorite stretch. A half day such as the Prestige Rent small-group tasting from ~$101 feels relaxed in spring, and you come back to Florence with energy left for the evening. Our page on choosing a half day or a full day covers that trade-off.
Late spring brings more visitors, and holiday weekends such as Easter fill quickly. If your dates are fixed, book once your flights are settled rather than waiting until you arrive.
July and August, heat and crowds
High summer in Florence is hot. Daytime highs often reach 32–35 °C (90–95 °F), and the countryside is not much cooler at midday. Walking through vineyards and standing on terraces can feel heavy in that heat.
The tours still run, and the listings for tour 1 and tour 4 name air-conditioned vehicles. Cellars are cool, which helps. The harder part is the time outdoors between stops, and a long day in the sun after several pours is tiring for anyone.
If summer is your only window, we would lean toward a shorter tour and plenty of water. The 11-hour day with Siena and San Gimignano is a long one in August, with uphill walking in both towns.
November to March, quiet cellars
Winter is the off-season in the vineyards. The vines are bare and the days short, often cold and damp. On the other hand, the cellars stay open, groups are smaller and the hosts have more time to talk.
If wine matters more to you than views, winter is a fair choice. Our guide on what ends up in your glass explains the labels you will taste, which do not change with the weather outside.
One tour changes its route in winter. The Gray Line Florence hill-town day drops Monteriggioni from November to March, and the day ends about 30 minutes earlier. Dress for cold stone rooms and bring a waterproof layer.
Three wineries and a long lunch, any month
Towns of Italy runs a small-group day to three estates in the Chianti hills, with an olive oil mill, a stop in Greve in Chianti and a sit-down Tuscan lunch. It runs rain or shine, and the cellars are the same in May as in January.
Rain, holiday weeks and booking ahead
Tours 1 and 2 both say they go ahead rain or shine. A wet day still has cellars, tastings and lunch indoors, but the vineyard walks get shorter and the views from the hills turn gray.
Holiday weeks sell out first, especially for the smaller vans. Every listing we read lets you cancel for free up to 24 hours before the start, so booking early costs very little flexibility. Our price comparison of all five tours helps you pick before the seats go.
If you travel with children or with someone who does not drink, the season matters less than the tour itself. The page on kids, teens and non-drinkers lists the age limits.
Fitting a tour into your Florence stay
Avoid putting the wine tour on your last day. If you feel unwell or a strike disrupts the morning, a spare day lets you move it. One free afternoon after a half day also gives you time for a nap and a slow dinner.
Start times differ by tour and option, so check the listing. One reviewer on tour 1 mentions a 9 am start, and some tours also run later in the day. A later departure can help in summer, when the hottest hours fall around midday.
Most tours meet near Santa Maria Novella station or near Santa Croce. Our map of where the wine tours start shows both points, and the guide to buying and shipping bottles helps if you plan to bring a case home.