Castellina in ChiantiOvernight baseFlorence–Siena road2026 pricesUpdated 8 min read
Castellina in Chianti Wine Guide: Best Wineries, Tastings & Things to Do
Castellina in Chianti is one of the best towns for travellers who want to get deeper into Chianti than a quick excursion from Florence allows. It sits on the route between Florence and Siena and works particularly well as an overnight base.
A barrel cellar in Chianti Classico. Around Castellina the estates sit close enough to town that two cellar visits and lunch fit easily into one day.
This page covers Castellina and the estates around it. For all nine Chianti towns, the SR222 and the 11 UGAs, start with our Chianti wine region guide. If you are coming from Florence for a single day, our Greve in Chianti guide covers the easier town.
Check availability — From Siena: Chianti and Castles Tour with Wine Tastings
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The one-line answer
Choose Castellina if you have two or more days in Chianti and want to sleep among the vineyards. For a single day trip from Florence, Greve is the easier town.
Start here
Why choose Castellina
Choose Castellina for:
a central Chianti position;
excellent winery access;
a historic town atmosphere;
road trips between Florence and Siena;
a quieter alternative to Greve.
Castellina is about an hour from Florence by road and 20 to 40 minutes from Siena. That is a little far from Florence for a relaxed half day, which is why Castellina suits an overnight stay: tour minivans pass through during the day, and in the evening the old centre is quiet.
Other experiences you might enjoy
Worth adding to your itinerary
Castellina sits in the middle of the Chianti Classico zone on the road between Florence and Siena, with Radda and Gaiole a short drive east and Greve and Panzano to the north. From a Castellina base, San Gimignano's Vernaccia and Brunello in Montalcino are both day trips. If you have not chosen a format yet, start with our Chianti tours guide. The widget below shows live availability for related Tuscany wine experiences.
Best wineries near Castellina
Five estates cover the range around Castellina, from one of the oldest names in Chianti to a small family producer.
Castello di Fonterutoli / Mazzei Historic producer
A historic producer and one of the strongest wine-focused destinations near town. The Mazzei family has owned Fonterutoli, a hamlet just south of Castellina on the road to Siena, since 1435, and the cellar is cut into the rock beneath the estate. The estate's own guided visit is sold on GetYourGuide: the Fonterutoli Wine Tour with Tasting → runs about an hour and a half with a wine expert, covers the family history and how the wines are made and aged, and finishes with four wines and the estate's extra virgin olive oil, from $94. It is newly listed and has no published rating yet, so book it for the estate itself.
Castellare di Castellina Serious Chianti estate
A serious estate with a strong Chianti identity, in the hills outside town. It sells no visits through GetYourGuide or Viator, so contact the estate directly to ask about a tasting.
Poggio Amorelli Accessible tasting
An accessible tasting experience. The estate offers seated tastings of its Chianti Classico, including the Riserva, and a Tuscan lunch, booked directly with the winery.
Querceto di Castellina Wine and a room
Wine plus accommodation: Querceto has rooms as well as a cellar, so it is one of the simplest ways to taste and stay the night in the same place. Rooms are listed on Booking.com: Querceto di Castellina →
Fattoria Pomona Smaller scale
A smaller-scale experience at a family estate. Small producers need notice, so arrange the visit a few days ahead.
Of these five, only Fonterutoli sells a visit through GetYourGuide, and that listing is new. Castellare, Poggio Amorelli, Querceto and Pomona take direct bookings. The well-reviewed way to taste around Castellina without a car is a tour from Siena that stops in town, below.
From $96·4.56★ (821 reviews) ·5 hours from Siena·Free cancel · 24h
A five-hour minivan trip from central Siena that stops in Castellina in Chianti and visits two wineries, with medieval castles and villages along the way. With more than 800 reviews it is the most-reviewed tour we found that stops in Castellina, and the five-hour length leaves your evening in Siena free.
Castellina's covered medieval passage is one of the town's most distinctive features. The Via delle Volte runs along the inside of the old walls under a vaulted roof, part of the defences Florence built here in the 15th century, and today it is lined with shops and restaurants.
Pair it with:
the Rocca, the fortress on Piazza del Comune;
the archaeological museum inside the Rocca, the Museo Archeologico del Chianti Senese, with Etruscan finds from Castellina, Radda, Gaiole and Castelnuovo Berardenga;
viewpoints over the vineyards from the edge of the old town;
an enoteca tasting, the easy way to try several Castellina producers without driving to each.
About ten minutes' walk north of the centre, the Etruscan tumulus of Montecalvario dates from the 7th century BC, and finds from its burial chambers are in the museum. Check the museum's opening hours before you go.
The Castellina UGA
Castellina is one of Chianti Classico's recognised UGAs (Unità Geografiche Aggiuntive, or additional geographical units). The 11 are Castellina, Castelnuovo Berardenga, Gaiole, Greve, Lamole, Montefioralle, Panzano, Radda, San Casciano, San Donato in Poggio and Vagliagli.
For enthusiasts, tasting Gran Selezione or other geographically identified wines from Castellina adds another layer to the visit: you can compare the place, not only the producer. Our Tuscan wine explainer covers what Gran Selezione means on the label.
Castellina vs Greve
Choose
For
Greve
An easy Florence day trip · public transport · a first visit
Castellina
An overnight stay · deeper wine touring · a Florence-to-Siena road trip
Greve is about 40 minutes from Florence and has a regional bus service, which makes it the simpler first visit. Castellina is further south and closer to Siena, so it suits travellers who are staying in Chianti or driving between the two cities. The Greve in Chianti guide covers the town and its wineries in the same detail as this page.
Castellina vs Radda
Both are excellent. Castellina is slightly more practical, on the main Florence–Siena axis. Radda is more secluded, further into the hills to the east, and suits a slower stay.
With a car, the two combine easily: Radda and Gaiole make the natural second day from a Castellina base.
A one-day itinerary
MorningWinery near Fonterutoli
Start just south of town while your palate is fresh. Fonterutoli's own visit takes about an hour and a half.
LunchCastellina
Eat in town, along the Via delle Volte or near the Rocca.
AfternoonSecond winery
Castellare, Poggio Amorelli or Pomona, booked directly. Two visits is the right number for one day.
Late afternoonVia delle Volte and town
Walk the covered passage and the old centre once the day visitors have gone.
Two wineries, one evening
Book both tastings before you arrive. The smaller estates around Castellina need an appointment, and an evening in town is easier to enjoy when the driving is done.
From Florence
Castellina works best on a full day, not a short half-day. At about an hour each way by road, a half day leaves time for one tasting and little else. If you are coming from Florence without a car, Greve is the easier town; our wine tours from Florence guide compares the day trips that leave from the city.
From Siena
From Siena, Castellina is a very natural Chianti destination, 20 to 40 minutes away, and often more sensible than driving all the way north to Greve. Both Siena tours on this page stop in Castellina, and our wine tours from Siena guide covers the rest of what leaves from the city.
Frequently asked — Castellina in Chianti
Is Castellina in Chianti worth visiting?
Yes, especially for wine-focused travellers. Fonterutoli and several other estates are on the edge of town, and the old centre with the covered Via delle Volte and the Rocca is a pleasant place to spend an evening.
How many wineries should I visit around Castellina?
Two. One in the morning, lunch in Castellina, and a second in the afternoon leaves time for the town before dinner.
Should I stay overnight in Castellina?
Yes, if you have two or more Chianti days. Castellina works best as a base: two wineries on the first day, then Radda and Gaiole on the second.
Is Castellina better than Greve?
Not universally. Greve is easier, especially on a day trip from Florence or by public transport. Castellina is deeper and more atmospheric, and suits an overnight stay or a road trip toward Siena. Our Chianti Classico bases ranked compares it with Panzano, Radda and Greve.
How far is Castellina in Chianti from Florence and Siena?
About an hour from Florence by road and 20 to 40 minutes from Siena, which is why it suits travellers based in Siena or driving between the two cities.
Our recommendation
Castellina is one of the best places to stop treating Chianti as a day trip.
Stay overnight, visit two wineries, walk the town after the tour buses leave, and use it as a base for Radda and Gaiole the next day.
A cheaper small-group trip from Siena with free time in Castellina, and an organic estate near Radda for the second day of a stay.
Free time in Castellina
From Siena: Chianti Wine Tour with Castle Visit & Tastings
From $55·4.59★ (54 reviews) ·5 hours, max 15·Free cancel · 24h
A castle visit, winery tastings with olive oil and balsamic vinegar, and free time in Castellina in Chianti itself, for $41 less than the castles tour above. Its 54 reviews are a much smaller record, so read the recent ones before booking.
From $45·4.87★ (458 reviews) ·2 hours, at the winery·Free cancel · 24h
A two-hour visit to Fattoria di Montemaggio, a small family-run organic winery outside Radda in Chianti, with the winemaking explained before the tasting. You meet at the estate, so you need your own transport, and the last stretch of road is gravel.
