Villas in Gaiole in Chianti
Gaiole in Chianti suits wine lovers and walkers who want castles and unpaved roads in the Chianti hills. Nearly all homes have a private pool. The town is small and the homes are spread over the surrounding hamlets, so plan on driving every day.
- Villas
- 22
- From, per week
- £424
About Gaiole in Chianti
Gaiole is a small town of under 3,000 people at about 360 metres, with Florence some 40 km north-west and Siena some 15 km south-west. It began in the 13th and 14th centuries as a merchant town for the castles around it, and its centre is a street-square along via Ricasoli with a neo-Gothic church, San Sigismondo. The castles are the reason to come. Brolio, an 11th-century castle and vineyard that belonged to the Ricasoli family, and Meleto, about 2 km out, are the best known, and a castles route of about 32 km links several more. The municipality takes in 21 hamlets, and the homes are spread around them rather than in the town. Nearly all have a private pool, a typical one sleeps about four, and some have a fireplace.
Is Gaiole in Chianti right for you?
- Best for
- Wine, castles and cycling on unpaved roads, with a pool
- Not for you if
- You want a beach, nightlife or to leave the car parked all week.
Near Gaiole in Chianti
Castello di Brolio
An 11th-century castle and vineyard that belonged to the Ricasoli family, reached by road from Gaiole.
Castello di Meleto
A late 12th-century castle about 2 km from Gaiole, turned into a villa in the 18th century, with a small theatre.
Strada dei Castelli
A castles route of about 32 km around Gaiole, taking in Cacchiano and Monteluco among others.
San Sano
A Romanesque village in the Gaiole area, easy to combine with a tour of the castles.
Getting to Gaiole in Chianti
Florence airport is the usual arrival point, about an hour by road for the 62 km. Public transport has no direct link: it means a train to Montevarchi-Terranuova then a taxi. Hire a car, since hamlets, castles and wineries are only reached by road.
When to go to Gaiole in Chianti
L'Eroica, a ride on antique bicycles over the unpaved white roads, starts and finishes in Gaiole on the first Sunday in October, and the festivities around it last a full week, so book early if you plan to be here then. Outside that week the town is small and the castles and wineries keep their own hours, so check opening times before a winter visit.
Villas in Gaiole in Chianti
3-star property
3-star property
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2-star property
2-star property
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2-star property
2-Bedroom Home, Gaiole in Chianti
Gaiole in Chianti, Tuscany Chianti, Italy
4
2
0
Air ConBBQParking+9 more
from£173
per night
4-star property
Montechioccioli
Gaiole in Chianti, Tuscany Chianti, Italy
12
6
0
BBQDishwasherFireplace+12 more
3-star property
Montechioccioli
Gaiole in Chianti, Tuscany Chianti, Italy
6
2
0
Air ConBBQDishwasher+13 more
from£61
per night
3-star property
Montechioccioli
Gaiole in Chianti, Tuscany Chianti, Italy
6
2
0
Air ConBBQDishwasher+13 more
from£61
per night
4-star property
4-Bedroom Home, Gaiole in Chianti
Gaiole in Chianti, Tuscany Chianti, Italy
9
4
0
BBQParkingDishwasher+9 more
from£271
per night
3-star property
Il Cinghiale
Gaiole in Chianti, Tuscany Chianti, Italy
6
3
0
Air ConBBQDishwasher+10 more
from£74
per night
3-star property
Gaiole Apartament
Gaiole in Chianti, Tuscany Chianti, Italy
2
1
0
DishwasherMicrowaveParking+5 more
from£71
per night
5-star property
5-star property
5-star property
Belvedere
Gaiole in Chianti, Tuscany Chianti, Italy
6
3
0
Air ConBBQDishwasher+11 more
from£178
per night
Gaiole in Chianti villa holidays: questions answered
What is L'Eroica in Gaiole in Chianti?
A ride on antique bicycles held on the first Sunday in October, starting and finishing in Gaiole. Riders use the unpaved white roads of the Chianti hills, and the festivities last a full week, so the town is busy.
Is Gaiole in Chianti good for wine?
Yes. Chianti Classico DOCG wine and DOP olive oil are produced here, and the Chianti Classico Wine and Oil Trail runs between Florence and Siena. Brolio is a castle and vineyard.
How far is Gaiole in Chianti from Florence airport?
About an hour by road, roughly 62 km. By train it is a long trip, because you take the train to Montevarchi-Terranuova and finish in a taxi.
Which castles can I visit near Gaiole in Chianti?
Brolio and Meleto are the best known, with Cacchiano and Monteluco on the castles route and Tornano, another castle with a vineyard, nearby. Hours differ for each, so check before driving over.
Is Gaiole in Chianti walkable?
The centre is small, built around one street-square on via Ricasoli. Most homes are in outlying hamlets across the hills, so check the distance to the town before assuming you can walk in.
Nearby towns to Gaiole in Chianti
Written by the TrustedVillas team. Last reviewed October 2026.
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