Call us on: 1-800-454-5922 Toll Free
Email Address

  • Gaiole

    Gaiole in Chianti
    Situated on the road ss408, from Siena to Montevarchi.
    Gaiole in Chianti owes its development to its position in the valley where an important market for the local populations was centered around the year 1000.
    Its name likely comes from "gaggiolo" used to indicate a large forest.
    After 1300 Gaiole became important not only as a market but as a tertiary city of the League of Chianti, Florence's administrative and political instrument.
    Gaiole was not only an important commercial centre, but it was also important to the clergy, this is evident by the many parish churches and abbeys.

  • Gaiole in Chianti Castles

    The Chianti is full of beautiful castles. Some of the castles can only be seen from the outside, others the gardens can be visited. 
    Take a morning to visit the castles around Gaiole in Chianti:

    Castello di Meleto
    Castello di Brolio
    Castello di Spaltena
    Castello di Montegrossi
    Badia a Coltibuono
    Castello di Tornano
    Castello di Cacchiano

    For more information about the Chianti castles look at this website:

  • Wine tasting around Gaiole

    Wine tasting is an important part of any holiday in Tuscany and especially in the Chianti. Around Gaiole there are many estates where this can be done. Here are a few, with their websites for further information :

    Castello di Brolio -
    Dievole -
    Cantalici -
    Castello di Meleto -
    Casanuova di Ama -
    Castello di Ama -

  • L'Eroica - bicycle event

    Gaiole is famous for a vintage bicycle race which is held in October. The entire route is permanently marked for visitors to follow at any time of the year. In the town square there is a small shop which sells items from the Eroica and provides as small museum about it.
    Have a look at our information about the Eroica here
    Our blog written by a participant of the event

  • Events and festivals

    Throughout the year there are several events and festivals occuring in the area of Gaiole.
    For a calendar of events visit:

    Municipality website: (in Italian only)
    Website with events all over the Chianti:

    Some of the most popular events are:

    Cantine aperte -
    L'Eroica -

  • Hamlets to visit around Gaiole​

    San Donato in Perano
    San Donato in Perano is a small medieval hamlet which is built around the San Donato chapel. It's located a short distance away from Gaiole and is worth a visit.
    Make sure you stop at Castello di San Donato in Perano for a wine tasting  -

  • Badia Coltibuono

    The abbey of San Lorenzo is commonly called Badia Coltibuono. Formerly an abbey, it has been transformed into a villa. It is located within the municipality of Gaiole in Chianti, only a short drive away from the town.
    The property is now a wine estate with agriturism which does wine and olive oil tastings and cooking courses. On site there is a small shop selling local products.

  • Vertine

    Vertine is an enchanting, stone-built, village located on a hill a couple of kilometres from Gaiole. It has been well restored to keep all its original charm. In the village is a small characteristic enoteca 'wine bar', La Vineria, where you can get a bit to eat together with an excellent glass of wine.

  • Museums and Tourist office

    Tourist Information Office
    Located in the main square
    Open from:
    From the 1st of april until the 31st of October
    Every day: 10.00-13/ 15.00-18.00

Experience an official tuscany tour with

Half Day Chianti Wine Tour with Private Luxury Van

Visit some of the most famous vineyards, see their wine cellars and taste excellent wines on this 5-hour tour. Also visit small villages such as Greve, Castellina and Radda in Chianti and ancient castles, hidden among green hills and surrounded by vineyards and olive groves. This tour is a perfect combination of culinary delights, arts and culture, and your private drive will take you to experience it all.

from 415,72 US Dollar

Private Tour of Siena and San Gimignano

Devoting an entire morning to Siena is a unique opportunity to visit its historic center, its monuments and discover all the secrets that lie behind one of the most passionate competitions in Italy: the Palio of Siena.
San Gimignano’s historical center has been declared a UNESCO world heritage site in 1990 for having preserved almost perfectly the features of the twelfth and thirteenth centuries city.
Private Tour for small groups

  • Departure from an agreed meeting point or from your hotel
  • Professional Guide
  • Visit of Siena
  • Typical tuscan lunch
  • Visit of San Gimignano
  • Return to an agreed meeting point or to your hotel
  • About 8 hours tour, lunch included

from 503,9 US Dollar

Let's pasta! Pasta cooking class in central Florence

Enjoy a Pasta cooking class with great typical Italian recipes and taste the fruit of your hard work in the city center of Florence.

from 94,48 US Dollar

Photography Bike Tour of Florence

Lense on Florence: take a private guided trip through the historical centre of Florence.
Learn about the art and history of this city, see and photograph some of its most compelling views and highlights.

from 36,53 US Dollar
Villa finder