Chianti Tours &
Things to Do
Discover the best Chianti tours and things to do in the rolling wine country between Florence and Siena: taste Chianti Classico at hilltop wineries, savour Tuscan cooking classes, drive the vineyard-lined countryside, visit medieval Siena and San Gimignano and tour castle estates. Compare top-rated experiences and plan the perfect trip.
rating
Explore Chianti by interest
Whatever brings you to Chianti — world-class museums, the river, or a long lunch — start with the experiences travellers love most.
Wine tasting
Chianti Classico.
ExploreFrom Florence
Easy day trip.
ExploreTuscan countryside
Rolling hills.
ExploreSiena & San Gimignano
Medieval towns.
ExploreFood & cooking
Tuscan flavours.
ExploreVespa tours
Scoot the hills.
ExploreCastle wineries
Historic estates.
ExploreChianti highlights
Wine & countryside.
ExploreTop attractions in Chianti
The landmarks that define the city — and the tickets and tours that get you in, often skipping the line.
Wine Tasting
Chianti Classico.
From Florence
Easy day trip.
Tuscan Countryside
Rolling hills.
Siena & San Gimignano
Medieval towns.
Food & Cooking
Tuscan flavours.
Vespa Tours
Scoot the hills.
Castle Wineries
Historic estates.
Chianti
Wine country.
Region awayWine Tasting
Chianti Classico.
1 hr awayFrom Florence
Easy day trip.
Region awayTuscan Countryside
Rolling hills.
Day trip awaySiena & San Gimignano
Medieval towns.
Region awayFood & Cooking
Tuscan flavours.
Region awayVespa Tours
Scoot the hills.
Know before you go
Short, straight answers to the questions every Chianti visitor asks before booking.
Spring (Apr–Jun)
Warm and green — ideal for the hills.
Harvest (Sep–Oct)
The grape harvest, the region’s finest time.
Summer (Jul–Aug)
Hot and busy, but golden landscapes.
Winter (Nov–Mar)
Quiet and cool, cosy for tastings.
For wine
September and October for the harvest.
Best overall
Late spring and early autumn for warm days.
One day
A wine tasting and countryside drive.
Two days
Add a cooking class and Siena.
Three+ days
Add San Gimignano and castle estates.
For wine
A day of cellar tastings.
For food
A Tuscan cooking class.
For culture
Siena and San Gimignano.
Tours
Wine and countryside tours cover the region.
By car
A car is ideal for the scenic wine roads.
By Vespa
Vespa tours are a fun way to explore.
On foot
The hilltop towns are walkable.
Where to stay
Stay at a countryside agriturismo.
Euro
Italy uses the euro; cards widely accepted.
Wine tastings
Book cellar visits ahead in high season.
Cooking classes
Come hungry — classes end with lunch.
Countryside
Bring a camera for the cypress roads.
Towns
Pair Siena with San Gimignano in a day.
Driving
Have a designated driver for tastings.
Combos
Some tours pair wine with the towns.
Wine tours
Cellar tastings fill up — book ahead.
Cooking classes
Small classes fill up — reserve early.
Florence trips
Day trips fill up — book ahead.
Vespa tours
Vespa tours fill up — reserve early.
Town tours
Siena tours fill up — book ahead.
Harvest
September and October are busiest — book far ahead.
Wine tour
Around €55–90 for a Chianti wine tasting.
Florence trip
About €51–90 for a day trip from Florence.
Cooking class
Roughly €65–110 for a class with lunch.
Town tour
Around €130 for a Siena and San Gimignano day.
Vespa tour
About €120 for a Vespa day tour.
How to save
Join group tours to save over private ones.
Chianti through the seasons
What's best, how busy it gets, and one booking tip for each time of year.
- Best for
- Green hills.
- Crowds
- Booking tip
- Great.
- Best for
- Golden land.
- Crowds
- Booking tip
- Hot.
- Best for
- Wine harvest.
- Crowds
- Booking tip
- Best.
- Best for
- Cosy tastings.
- Crowds
- Booking tip
- Quiet.