Things to do in Chianti for first-time visitors
Landing in Florence or Siena with one free day and a vague idea of "going to Chianti" is normal. The problem is that search results throw tours, villages and wineries at you with no clear order, so it is easy to bounce between ten tabs and still not know what to actually do.
This page is a simple first time guide to things to do in Chianti. How to mix a wine tour with a hilltop town and a proper Tuscan lunch, where to find views without spending the whole day in the car, and how to spread your time across more than the same two famous villages that every list repeats.
Navigate your things to do in Chianti guide
There are a lot of ways to spend a day in Chianti and most of them look great in photos. This guide keeps it simple for a first visit: a few core experiences, ideas if you have more time, and honest tips so you do not spend the whole day driving or ticking off a rushed checklist.
- Top things to do in Chianti on a first visit
- More ideas if you have extra time in Tuscany
- Visitor tips so you do not waste your one Chianti day
- Questions about things to do in Chianti
Top things to do in Chianti on a first visit
- Join a wine tour: the easiest way to see vineyards, taste a few glasses and not worry about roads or parking.
- Walk a hilltop town: spend real time in at least one village square instead of only stopping for photos.
- Eat a long Tuscan lunch: one unhurried meal in the countryside will stay with you longer than three quick tastings.
- Drive or ride a scenic stretch: even a short piece of the Chiantigiana road gives you that classic Tuscany view.
- Take a vineyard walk: if you can, leave the tasting room for ten minutes and actually walk between the rows.
One simple option: let a Chianti wine tour handle the logistics
If planning stresses you out, the cleanest first step is to book a small group Chianti wine tour from Florence or Siena and build the rest of your day around it. You get transport, a couple of wineries and usually a village or viewpoint without having to read every bus timetable or wine map.
The tours below are a starting point, not the only good options. Read how long the day really is, how many stops it includes, and how big the group is, then add your own small things to do before or after in Florence, Siena or a nearby village.
Six easy ways to spend a day in Chianti
More ideas if you have extra time in Tuscany
Once you have covered the basics, there are plenty of small add-ons if you stay longer in Chianti or return for a second visit.
- Combine a Chianti morning with an afternoon in Siena or San Gimignano instead of trying to do two full days in one.
- Visit an olive oil mill around Impruneta, San Casciano or the hills near Barberino Tavarnelle to see how the other famous Tuscan product is made.
- Follow a short signed trail between villages like Volpaia and Radda or around San Gusme if you want a low key hike with real views.
- Swap the car for an e-bike or Vespa tour for one part of the day so you are not always behind glass.
- Book a simple cooking class on a farm and link it with a vineyard visit instead of adding a third or fourth winery.
Visitor tips for planning what to do in Chianti
- Do less, but do it properly: two or three main things in a day is enough - for example a village, one winery and lunch - anything more turns into a blur.
- Group your stops: pick one area (around Greve, around Castellina, around Radda) instead of zigzagging the whole region in one go.
- Book key pieces ahead: popular wineries and countryside restaurants often fill up, especially for lunch with a view, so reserve those parts first.
- Watch opening days: many places in Tuscany close one day a week or for a long lunch break, so check hours to avoid finding your chosen stop shuttered.
- Think about who is driving: if nobody wants to be the sober driver, choose a tour or private driver rather than trying to juggle tastings and car keys.
- Leave space for nothing: the best moments are often ten quiet minutes on a wall or terrace, so do not schedule every minute of the day.
Navigate Chianti with an easy-to-use directions guide
10 questions about things to do in Chianti
1. How many days should I spend in Chianti on a first trip?
If you are based in Florence or Siena, one full day is enough to get a feel for Chianti, two gives you time for both wine and slower exploring. A longer stay of three to four nights works well if you want an agriturismo base and day trips out from there.
2. Is it worth visiting Chianti if I do not drink much wine?
Yes, as long as you choose the right kind of day. Focus on villages, views, food and short walks between vineyards, and treat tastings as a small part of the picture instead of the main event.
3. Do I need a car to enjoy things to do in Chianti?
A car or driver gives you the most freedom, but you can still see a lot on an organized tour from Florence or Siena. Public buses reach some towns, yet they are slow and not great for hopping between villages and vineyards in one day.
4. Which villages are best for a first-time visit?
Greve, Castellina and Radda are easy places to start because they have clear centers, good views and plenty of cafes. If you have more time, smaller spots like Montefioralle, Volpaia or San Gusme feel quieter and more tucked away.
5. Can I combine Chianti with another Tuscany highlight in one day?
You can, but keep it light. A short stop in Siena or San Gimignano at the start or end of the day works, trying to do a full city visit and a full Chianti loop on the same day usually feels rushed.
6. When is the best season for things to do in Chianti?
Late April to June and September to mid October are the easiest months for a first visit, with pleasant temperatures and vineyards looking their best. July and August can still be beautiful, just hotter and busier in the middle of the day.
7. Do I need to book wineries and restaurants in advance?
For weekends, high season and anywhere with a view, yes. Many estates and restaurants in Chianti work by reservation, especially for tastings with food. For simpler bars and cafes in town centers you can usually just walk in.
8. Are there things to do in Chianti with children?
Yes. Short vineyard walks, farm visits with animals, gelato stops in village squares and simple picnics at viewpoints all work well. Try to keep formal tastings short and leave space for play and breaks from sitting.
9. Can I see Chianti on a rainy day?
Rain changes the mood but not the basics. Views are moodier, walks between the vines get shorter, and you spend more time in cellars and tasting rooms. Many visitors end up enjoying wet days because places are quieter and conversations longer.
10. Is it better to base myself in Chianti or just do day trips?
If your time is short and you want museums and nightlife, staying in Florence or Siena and doing a day trip to Chianti keeps things simple. If you prefer quiet evenings, stars and early mornings with mist over vineyards, a few nights based in Chianti itself are worth the extra planning.