Title: 10 TOP Things to Do in Gaiole in Chianti November 2025 | Expedia.ca [Gaiole in Chianti Travel Guide](https://expedia.ca/Gaiole-In-Chianti.dx603149)[Hotels in Gaiole in Chianti](https://expedia.ca/Gaiole-In-Chianti-Hotels.d603149.Travel-Guide-Hotels)[Flights to Gaiole in Chianti](https://expedia.ca/Cheap-Flights-To-Gaiole-In-Chianti.d603149.Travel-Guide-Flights)[Gaiole in Chianti Car Rentals](https://expedia.ca/Car-Rentals-In-Gaiole-In-Chianti.d603149.Car-Rental-Guide)[Gaiole in Chianti Vacation Packages](https://expedia.ca/Gaiole-In-Chianti.d603149.Destination-Travel-Guides) # What to do in Gaiole in Chianti ## Activities, attractions and tours ## Visit Gaiole in Chianti Types of activities [Gaiole in Chianti travel guide](https://expedia.ca/Gaiole-in-Chianti.dx603149) ![Photo by Karen Dean](https://mediaim.expedia.com/destination/2/a2c6ad675bceb2a96f21b753e5375ee0.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Karen Dean](https://mediaim.expedia.com/destination/2/a2c6ad675bceb2a96f21b753e5375ee0.jpg) ![Photo by Lara Saade](https://mediaim.expedia.com/destination/2/b07660da931cdd6a0c5cf661c5f70168.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Lara Saade](https://mediaim.expedia.com/destination/2/b07660da931cdd6a0c5cf661c5f70168.jpg) ![Photo by Stewart Helfer](https://mediaim.expedia.com/destination/2/2ab8a77e0f73740d2d2dd988e2859f32.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Stewart Helfer](https://mediaim.expedia.com/destination/2/2ab8a77e0f73740d2d2dd988e2859f32.jpg) ![Photo "Gaiole in Chianti" by LigaDue (CC BY-SA) / Cropped from original](https://mediaim.expedia.com/destination/3/b8916e36658f4d94de7259069ba4cfbf.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [](https://mediaim.expedia.com/destination/3/b8916e36658f4d94de7259069ba4cfbf.jpg)[Photo](https://mediaim.expedia.com/destination/3/b8916e36658f4d94de7259069ba4cfbf.jpg) by [LigaDue](//commons.wikimedia.org/wiki/User:LigaDue) ([CC BY-SA](https://creativecommons.org/licenses/by-sa/4.0)) ![Photo "Gaiole in Chianti" by LigaDue (CC BY-SA) / Cropped from original](https://mediaim.expedia.com/destination/3/ad3f8e241b6d9745982b6dba2089973c.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [](https://mediaim.expedia.com/destination/3/ad3f8e241b6d9745982b6dba2089973c.jpg)[Photo](https://mediaim.expedia.com/destination/3/ad3f8e241b6d9745982b6dba2089973c.jpg) by [LigaDue](//commons.wikimedia.org/wiki/User:LigaDue) ([CC BY-SA](https://creativecommons.org/licenses/by-sa/4.0)) ## Gaiole in Chianti Attractions Let Expedia help you experience the best that Gaiole in Chianti has to offer! If you’re looking for fun itinerary ideas, we can provide you with a list of the top sightseeing attractions, as well as helping you to find unmissable activities. Whether you’re travelling with your family, planning a romantic trip with your loved one, or visiting on business, we’ll make it easy to plan an unforgettable holiday that checks all the boxes. #### Activities and Tours Gaiole in Chianti is crammed with must-see places to visit and things to do. We can help you decide where to stay, and make it a breeze to explore the surrounding areas with our guides on where to go, what to see and when to see it. No matter how long your stay, it’s easy to find places of interest in Gaiole in Chianti to make sure that you enjoy your experience to the fullest and don’t miss a thing. Leave the local knowledge to us and leave the hassle behind. If you’re planning a visit, why not check out our handy guides to places of interest in the area? You can browse lists of things to do, learn about the most popular attractions, and get help with planning the details of your trip. Expedia makes it easy for you to check out all the top sights. #### Gaiole in Chianti Attractions Expedia has something for everyone, so whether you’re planning to get active on a summer holiday, put a spring in your step with a romantic rendezvous, or pamper yourself with a leisurely winter trip, you’ll find plenty of attractions to keep you entertained. In addition to scheduling local tours, booking reservations and scoring advance event tickets, Expedia makes it easy to book your flight, hotel and rental car in advance, all on one consolidated travel itinerary, making for hassle-free travel and freeing you up to explore the sights of Gaiole in Chianti. Looking for things to do can be time consuming, but we can take the hassle out of planning your holiday. Whether you’re looking to get active in the great outdoors, sample the cuisine or catch up with the vibrant local culture, our guides to Gaiole in Chianti attractions ensure that you’ll have a successful trip, whatever the season. * * * - ![find price illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__find_price.svg) ### Explore activities Explore thousands of experiences from activities and attractions to day tours and transfer. - ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Book with ease Skip the line- book tickets online in minutes to top attractions with free cancellation on many activities. - ![trophy illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__trophy.svg) ### Treat yourself Members save % or more when you book activities. * * * ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=ACTIVITIES_BF_PROMO_603149) ## Recommended things to do in Gaiole in Chianti | Number of things to do | 219 | | --- | --- | | Cheapest thing to do on Expedia | [Siena Walking Tour with Audio and Written Guide by a local](https://expedia.ca/things-to-do/siena-walking-tour-with-audio-and-written-guide-by-a-local.a48944099.activity-details): CA $11 | | Top 5 things to do | - [Siena, San Gimignano, Monteriggioni and Chianti with Lunch & Wine Tasting](https://expedia.ca/things-to-do/san-gimignano-siena-and-chianti-with-lunch-wine-tasting.a329818.activity-details) - [Siena: Civic Museum and Palazzo Pubblico Entry Ticket](https://expedia.ca/things-to-do/siena-civic-museum-and-palazzo-pubblico-entry-ticket.a50461757.activity-details) - [Chianti Half Day Wine Tour from Florence](https://expedia.ca/things-to-do/chianti-half-day-wine-tour-from-florence.a510796.activity-details) - [Siena: Siena Cathedral and Piccolomini Library Entry Ticket](https://expedia.ca/things-to-do/siena-siena-cathedral-and-piccolomini-library-entry-ticket.a47961267.activity-details) - [Siena, San Gimignano, Monteriggioni & Chianti from Florence](https://expedia.ca/things-to-do/siena-san-gimignano-monteriggioni-chianti-from-florence.a553041.activity-details) | | Half-day tours | - [Exclusive Wine Tasting in the Historic Centre of Siena](https://expedia.ca/things-to-do/exclusive-wine-tasting-in-the-historic-centre-of-siena.a48855082.activity-details) - [Discover Chianti Through its Wines](https://expedia.ca/things-to-do/discover-chianti-through-its-wines.a1142212.activity-details) - [Skip the Line: Siena City and Duomo Walking Tour](https://expedia.ca/things-to-do/skip-the-line-siena-duomo-and-city-walking-tour.a337428.activity-details) - [Montefioralle Winery - Tour and Wine Tasting in Chianti](https://expedia.ca/things-to-do/montefioralle-winery-tour-and-wine-tasting-in-chianti.a49047097.activity-details) - [Wine Experience in an Organic Chianti Winery](https://expedia.ca/things-to-do/wine-experience-in-an-organic-chianti-winery.a48261314.activity-details) | | With kids | - [Siena, San Gimignano, Monteriggioni and Chianti with Lunch & Wine Tasting](https://expedia.ca/things-to-do/san-gimignano-siena-and-chianti-with-lunch-wine-tasting.a329818.activity-details) - [Siena: Civic Museum and Palazzo Pubblico Entry Ticket](https://expedia.ca/things-to-do/siena-civic-museum-and-palazzo-pubblico-entry-ticket.a50461757.activity-details) - [Chianti Half Day Wine Tour from Florence](https://expedia.ca/things-to-do/chianti-half-day-wine-tour-from-florence.a510796.activity-details) - [Siena: Siena Cathedral and Piccolomini Library Entry Ticket](https://expedia.ca/things-to-do/siena-siena-cathedral-and-piccolomini-library-entry-ticket.a47961267.activity-details) - [Siena, San Gimignano, Monteriggioni & Chianti from Florence](https://expedia.ca/things-to-do/siena-san-gimignano-monteriggioni-chianti-from-florence.a553041.activity-details) | ## What to do in Gaiole in Chianti * * * ### Discover the most popular places to visit in Gaiole in Chianti ![Meleto Castle](https://mediaim.expedia.com/destination/2/b07660da931cdd6a0c5cf661c5f70168.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Meleto Castle Find out about the history of Gaiole in Chianti when you spend time at Meleto Castle. Discover the beautiful countryside in this walkable area, or enjoy its local tours. [](https://expedia.ca/Meleto-Castle-Gaiole-in-Chianti.d6186842.Vacation-Attraction) #### Castle of Brolio 4.5/5(3 reviews) You can find out about the history of Gaiole in Chianti with a stop at Castle of Brolio. Discover the beautiful countryside and wineries in this walkable area. [](https://expedia.ca/Castle-Of-Brolio-Gaiole-in-Chianti.d6249465.Vacation-Attraction) #### Badia a Coltibuono You can enjoy a tasting or tour at Badia a Coltibuono during your travels to Badia Coltibuono. Discover the beautiful countryside in this relaxing area, or enjoy its local tours. [](https://expedia.ca/Badia-A-Coltibuono-Gaiole-in-Chianti.d6292126.Vacation-Attraction) #### Cantalici Winery You can enjoy a tasting or tour at Cantalici Winery during your travels to Gaiole in Chianti. Discover the beautiful countryside in this walkable area, or enjoy its local tours. [](https://expedia.ca/Cantalici-Winery-Gaiole-in-Chianti.d553248621562144630.Vacation-Attraction) #### Medieval Tower of Barbischio Find out about the history of Gaiole in Chianti when you take a trip to Medieval Tower of Barbischio. Discover the beautiful countryside in this quaint area, or enjoy its local tours. [](https://expedia.ca/Medieval-Tower-Of-Barbischio-Gaiole-in-Chianti.d6238143.Vacation-Attraction) #### Gaiole in Chianti Stadium Catch an event at Gaiole in Chianti Stadium during your trip to Gaiole in Chianti. Discover the beautiful countryside and charming coffeehouses in this quaint area. [](https://expedia.ca/Gaiole-In-Chianti-Stadium-Gaiole-in-Chianti.d6238145.Vacation-Attraction) #### Church of San Sigismondo After visiting Church of San Sigismondo, make a plan to see the other sights and activities in Gaiole in Chianti. Discover the beautiful countryside in this walkable area, or enjoy its local tours. [](https://expedia.ca/Church-Of-San-Sigismondo-Gaiole-in-Chianti.d6238140.Vacation-Attraction) #### Castello di Meleto Cantina You can enjoy a tasting or tour at Castello di Meleto Cantina during your travels to Gaiole in Chianti. Visit the spas in this quaint area, or simply enjoy its wineries. [](https://expedia.ca/Castello-Di-Meleto-Cantina-Gaiole-in-Chianti.d873868973899513856.Vacation-Attraction) #### PoggioBrandani You can enjoy a tasting or tour at PoggioBrandani during your travels to Gaiole in Chianti. Discover the beautiful countryside and charming coffeehouses in this quaint area. [](https://expedia.ca/PoggioBrandani-Gaiole-in-Chianti.d553248621532500722.Vacation-Attraction) * * * Looking for fun things to do nearby? Check [things to do near me](https://www.expedia.ca/things-to-do-near-me) to find and book the best things to do, fun activities, and top attractions wherever you happen to be. * * * ## Day trip destinations from Gaiole in Chianti ![Siena](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/409000/409074-Siena.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Siena [](https://expedia.ca/Siena.dx9821) ![Radda in Chianti which includes heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157516-Chianti-Region.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Radda in Chianti [](https://expedia.ca/Radda-In-Chianti.dx601693) ## Frequently asked questions ### Is Gaiole in Chianti worth visiting? > Providing a mix of bars and pubs and walking trails, there's no shortage of things to do in Gaiole in Chianti. When you're here, head to Castello di Albola, a key attraction in the area. ### How do I spend a day in Gaiole in Chianti? > Castello di Albola and Meleto Castle are two great places to start your adventures. Be sure to check out the retail and dining options in Gaiole in Chianti while you're here too. ### What is the top tourist attraction in Gaiole in Chianti? > Don't leave without checking out Castello di Albola, ranked the top tourist attraction in Gaiole in Chianti. ### Is three days enough to stay in Gaiole in Chianti? > Three days in Gaiole in Chianti is more than enough to visit the city's key attractions. Many travellers book for three days on average. Castello di Albola, Meleto Castle and Castello di Radda Winery are among the top-rated sights. Like to see more? Stick around a bit longer to visit nearby hotspots like Florence. ### Is Gaiole in Chianti a walkable city? > With vibrant neighbourhoods and top sights within walking distance of the city centre, Gaiole in Chianti is a great destination to see on foot. Wander between Meleto Castle and Badia a Coltibuono. Then take a stroll through Badia Coltibuono, located 3 kilometres from downtown, and Vertine, which is about 2 kilometres away. ### What are some activities to do in Gaiole in Chianti with kids? > If you're looking for tours and attractions for all ages, here are some fabulous ideas for what to do in Gaiole in Chianti with kids. > > > > - [Siena, San Gimignano, Monteriggioni and Chianti with Lunch & Wine Tasting](https://expedia.ca/things-to-do/san-gimignano-siena-and-chianti-with-lunch-wine-tasting.a329818.activity-details) > - [Siena: Civic Museum and Palazzo Pubblico Entry Ticket](https://expedia.ca/things-to-do/siena-civic-museum-and-palazzo-pubblico-entry-ticket.a50461757.activity-details) > - [Chianti Half Day Wine Tour from Florence](https://expedia.ca/things-to-do/chianti-half-day-wine-tour-from-florence.a510796.activity-details) > - [Siena: Siena Cathedral and Piccolomini Library Entry Ticket](https://expedia.ca/things-to-do/siena-siena-cathedral-and-piccolomini-library-entry-ticket.a47961267.activity-details) > - [Siena, San Gimignano, Monteriggioni & Chianti from Florence](https://expedia.ca/things-to-do/siena-san-gimignano-monteriggioni-chianti-from-florence.a553041.activity-details) ### What to do in Gaiole in Chianti for adults? > Buondonno Winery and Le Miccine are just a few of the things to do in Gaiole in Chianti. With lots of activities available, there's something here for everyone to explore. ### Are there free things to do in Gaiole in Chianti? > In Gaiole in Chianti, Church of San Sigismondo is an unmissable spot for anyone wishing to experience the city without opening their wallet. Also, wander around the other neighbourhoods and green spaces, and ask for recommendations from a local tour guide. It's a simple way to find out about the best free things to do in Gaiole in Chianti. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [5 Star Hotels in Chianti Region](https://www.expedia.ca/5Star-Chianti-Region-Hotels.s50-0-d603148.Travel-Guide-Filter-Hotels) - [Badia Coltibuono Hotels](https://www.expedia.ca/Badia-Coltibuono-Hotels.d553248635975857717.Travel-Guide-Hotels) - [Hotels near Castello di Radda Winery](https://www.expedia.ca/Castello-Di-Radda-Winery-Hotels.0-l553248621532501476-0.Travel-Guide-Filter-Hotels) - [Hotels near Castle of Brolio](https://www.expedia.ca/Castle-Of-Brolio-Hotels.0-l6249465-0.Travel-Guide-Filter-Hotels) - [Cavriglia Hotels](https://www.expedia.ca/Cavriglia-Hotels.d6025771.Travel-Guide-Hotels) - [Farmstay in Chianti Region](https://www.expedia.ca/Chianti-Region-Agritourism.d603148-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Chianti Region](https://www.expedia.ca/Chianti-Region-Apart-Hotels.d603148-aaApartHotels.Travel-Guide-Accommodation) - 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