Title: 10 TOP Things to Do in Gaiole in Chianti October 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. * * * ### Most fun & popular experiences in Gaiole in Chianti ### Tours & day trips [See all 231 activities](https://expedia.ca/things-to-do/search?&rid=603149&location=Gaiole+in+Chianti&filter.categories=ToursDayTrips) ![Siena, San Gimignano, Monteriggioni and Chianti with Lunch & Wine Tasting](https://mediaim.expedia.com/localexpert/329818/686ebe9b-4424-48e3-a5f6-94acd7591fdc.jpg?impolicy=resizecrop&rw=500&rh=280) ### Siena, San Gimignano, Monteriggioni and Chianti with Lunch & Wine Tasting 11h 8.6/10 131 reviews Free cancellation available CA $129 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/san-gimignano-siena-and-chianti-with-lunch-wine-tasting.a329818.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Chianti Half Day Wine Tour from Florence](https://mediaim.expedia.com/localexpert/510796/183e2e32-2bc9-4a2b-9b14-ce3b16c8add4.jpg?impolicy=resizecrop&rw=500&rh=280) ### Chianti Half Day Wine Tour from Florence 5h 30m 8.8/10 54 reviews Free cancellation available CA $80 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/chianti-half-day-wine-tour-from-florence.a510796.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Medieval Tuscany Experience: Monteriggioni and Val d'Orcia from Florence](https://mediaim.expedia.com/localexpert/46773619/ef900635-4e33-44a5-b043-5a52cc96c076.jpg?impolicy=resizecrop&rw=500&rh=280) ### Medieval Tuscany Experience: Monteriggioni and Val d'Orcia from Florence 11h 10/10 1 review Free cancellation available CA $90 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/medieval-tuscany-experience-monteriggioni-and-val-dorcia-from-florence.a46773619.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Siena, San Gimignano, Monteriggioni & Chianti from Florence](https://mediaim.expedia.com/localexpert/553041/def47daa-d183-43ae-81a6-3355ec60f5c9.jpg?impolicy=resizecrop&rw=500&rh=280) ### Siena, San Gimignano, Monteriggioni & Chianti from Florence 8h+ 8.6/10 24 reviews Free cancellation available CA $106 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/siena-san-gimignano-monteriggioni-chianti-from-florence.a553041.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![VIP Tour: Wine Tasting & Dinner in the Vineyards of Chianti](https://mediaim.expedia.com/localexpert/4100087/1564dd17-49f0-4fd1-b2ef-8c209068e6b7.jpg?impolicy=resizecrop&rw=500&rh=280) ### VIP Tour: Wine Tasting & Dinner in the Vineyards of Chianti 6h 30m 9/10 16 reviews Free cancellation available CA $197 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/vip-tour-wine-tasting-dinner-in-the-vineyards-of-chianti.a4100087.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Siena and San Gimignano: Small-Group Tour with Lunch from Florence](https://mediaim.expedia.com/localexpert/1137621/2ce6ba32-d99b-4556-8b0e-90305fa6c8e6.jpg?impolicy=resizecrop&rw=500&rh=280) ### Siena and San Gimignano: Small-Group Tour with Lunch from Florence 10h 10/10 13 reviews Free cancellation available CA $244 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/siena-and-san-gimignano-small-group-tour-with-lunch-from-florence.a1137621.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Chianti Authentic Experience with two Wine Tastings](https://mediaim.expedia.com/localexpert/177267/0ec73ce0-4260-4f3b-b3c2-f811015674a8.jpg?impolicy=resizecrop&rw=500&rh=280) ### Chianti Authentic Experience with two Wine Tastings 5h 7.2/10 56 reviews Free cancellation available CA $90 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/chianti-tour-with-two-wine-tastings-two-charming-villages.a177267.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Sunset in Siena and Chianti Dinner from Florence](https://mediaim.expedia.com/localexpert/561475/2cf9fcfa-f4ab-4a98-936a-3965c616eb6a.jpg?impolicy=resizecrop&rw=500&rh=280) ### Sunset in Siena and Chianti Dinner from Florence 7h 15m 8.4/10 5 reviews Free cancellation available CA $129 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/sunset-in-siena-and-chianti-dinner-from-florence.a561475.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena](https://mediaim.expedia.com/localexpert/1139506/ff1c8e1f-f674-45b9-b7da-daf2120ea7de.jpg?impolicy=resizecrop&rw=500&rh=280) ### Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena 9h 10/10 3 reviews Free cancellation available CA $295 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/small-group-brunello-di-montalcino-wine-tasting-trip-from-siena.a1139506.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Siena & San Gimignano Day Trip from Florence with Chianti Views](https://mediaim.expedia.com/localexpert/599682/9aaa51e2-9a73-4f4e-9476-329b0fe89b06.jpg?impolicy=resizecrop&rw=500&rh=280) ### Siena & San Gimignano Day Trip from Florence with Chianti Views 9h 8.8/10 18 reviews Free cancellation available CA $97CA $87 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/charming-tuscany-pisa-siena-san-gimignano-chianti-day-trip-with-wine.a599682.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ### Private & custom tours [See all 114 activities](https://expedia.ca/things-to-do/search?&rid=603149&location=Gaiole+in+Chianti&filter.categories=Privatecustomtours) ![Siena: Horseback Adventure in the Tuscan Countryside](https://mediaim.expedia.com/localexpert/48146663/553ab7a1-478e-488c-8bd8-29856eaee45e.jpg?impolicy=resizecrop&rw=500&rh=280) ### Siena: Horseback Adventure in the Tuscan Countryside 3h Free cancellation available CA $262 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/siena-horseback-adventure-in-the-tuscan-countryside.a48146663.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Tour of the historical cellars in Montepulciano](https://mediaim.expedia.com/localexpert/45270989/560c8d2e-6d5f-430d-95ec-8a2ac7eb560e.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tour of the historical cellars in Montepulciano 2h 30m Free cancellation available CA $97 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/tour-of-the-historical-cellars-in-montepulciano.a45270989.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Sarteano: Tasting of oils and bruschetta](https://mediaim.expedia.com/localexpert/48958555/73f80315-b232-4983-9833-86b88acc54fe.jpg?impolicy=resizecrop&rw=500&rh=280) ### Sarteano: Tasting of oils and bruschetta 45m 10/10 1 review Free cancellation available CA $13 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/sarteano-tasting-of-oils-and-bruschetta.a48958555.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Semi Private Siena and San Gimignano from Rome](https://mediaim.expedia.com/localexpert/585928/c0030797-f308-4ebb-a5a1-c623b1f1e14f.jpg?impolicy=resizecrop&rw=500&rh=280) ### Semi Private Siena and San Gimignano from Rome 12h Free cancellation available CA $1,278 includes taxes & fees per traveller\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/semi-private-siena-and-san-gimignano-from-rome.a585928.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Tasting with Private Walk in a Cellar in Tuscany](https://mediaim.expedia.com/localexpert/5138996/0c9827f3-6a87-4c8b-9354-4dbc7bd16f47.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tasting with Private Walk in a Cellar in Tuscany 2h Free cancellation available CA $41 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/tasting-with-private-walk-in-a-cellar-in-tuscany.a5138996.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence](https://mediaim.expedia.com/localexpert/1086118/531d041d-c763-468f-9088-d8df86bae6c2.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Tour in Siena, San Gimignano and Chianti Day Trip from Florence 8h Free cancellation available CA $1,130 includes taxes & fees per traveller\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/private-tour-in-siena-san-gimignano-and-chianti-day-trip-from-florence.a1086118.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Private Day Tour in Siena](https://mediaim.expedia.com/localexpert/3284713/4bd0ead8-6b79-42ee-affa-3ae66e2b087f.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Day Tour in Siena 10h Free cancellation available CA $983 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/private-day-tour-in-siena.a3284713.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Private Chianti wine tour](https://mediaim.expedia.com/localexpert/3073058/2016ffcb-0796-4ce4-a6af-6c2ec93f919f.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Chianti wine tour 5h CA $1,393 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/private-chianti-wine-tour.a3073058.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Private minivan excursion to Siena](https://mediaim.expedia.com/localexpert/47131856/8f8b6d7d-f307-4501-9254-64136e4d9a37.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private minivan excursion to Siena 5h Free cancellation available CA $1,080 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/private-minivan-excursion-to-siena.a47131856.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Private Taste of Tuscany Tour](https://mediaim.expedia.com/localexpert/49838127/2c8767a9-ec78-45f3-b3ce-7a8ff49db236.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Taste of Tuscany Tour 9h Free cancellation available CA $475 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/private-taste-of-tuscany-tour.a49838127.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ### Classes & workshops [See all 23 activities](https://expedia.ca/things-to-do/search?&rid=603149&location=Gaiole+in+Chianti&filter.categories=ClassesWorkshops) ![Siena: Pasta and Tiramisu Small Group Cooking Class with Wine](https://mediaim.expedia.com/localexpert/49774024/816fda58-95b9-44c9-9549-abf3115d8a54.jpg?impolicy=resizecrop&rw=500&rh=280) ### Siena: Pasta and Tiramisu Small Group Cooking Class with Wine 3h 10/10 2 reviews Free cancellation available CA $113 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/siena-pasta-and-tiramisu-cooking-class-with-wine.a49774024.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Siena countryside: cooking class in a real Tuscan farmhouse](https://mediaim.expedia.com/localexpert/48307488/2cdbdc4c-253d-4c58-ba14-f74d6d209c73.jpg?impolicy=resizecrop&rw=500&rh=280) ### Siena countryside: cooking class in a real Tuscan farmhouse 4h Free cancellation available CA $221 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/siena-countryside-cooking-class-in-a-real-tuscan-farmhouse.a48307488.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Tuscan Cooking Class in Central Siena](https://mediaim.expedia.com/localexpert/1052566/82a90dd7-1ba5-4ec6-b34a-3aa8b3dc5534.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tuscan Cooking Class in Central Siena 4h 8/10 4 reviews Free cancellation available CA $213 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/tuscan-cooking-class-in-central-siena.a1052566.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Florence, Chianti: Supertuscan Wine Tour Masterclass by a Wine Expert](https://mediaim.expedia.com/localexpert/550925/8e4d2349-b96b-4c6d-9321-c29c1e6e9f1e.jpg?impolicy=resizecrop&rw=500&rh=280) ### Florence, Chianti: Supertuscan Wine Tour Masterclass by a Wine Expert 6h 30m Free cancellation available CA $359CA $323 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/supertuscan-wine-tour-masterclass-by-a-wine-expert.a550925.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![From Siena: Tuscan Cooking Class in a Chianti Farm](https://mediaim.expedia.com/localexpert/231455/7790a6ab-f9cd-4b24-8215-1206bf690e72.jpg?impolicy=resizecrop&rw=500&rh=280) ### From Siena: Tuscan Cooking Class in a Chianti Farm 4h Free cancellation available CA $188 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/tuscan-cooking-class-from-siena.a231455.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Tuscan Culinary Secrets Unveiled: Cooking Class & Dinner](https://mediaim.expedia.com/localexpert/48178932/bdefa0b6-2268-4e23-95a2-0f7581dc2fd9.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tuscan Culinary Secrets Unveiled: Cooking Class & Dinner 4h Free cancellation available CA $229 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/tuscan-culinary-secrets-unveiled-cooking-class-dinner.a48178932.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![The art of the Italian Aperitivo with a local in Siena](https://mediaim.expedia.com/localexpert/872078/a6318d65-b1f5-4df4-afcb-f4c71db27463.jpg?impolicy=resizecrop&rw=500&rh=280) ### The art of the Italian Aperitivo with a local in Siena 2h Free cancellation available CA $172 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/the-art-of-the-italian-aperitivo-with-a-local-in-siena.a872078.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Wine Loves Food: The Perfect Tuscan Lunch & Wine Pairing Secrets](https://mediaim.expedia.com/localexpert/50040821/71d08f0c-f393-4378-b534-c24690ed0304.jpg?impolicy=resizecrop&rw=500&rh=280) ### Wine Loves Food: The Perfect Tuscan Lunch & Wine Pairing Secrets 2h Free cancellation available CA $62 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/wine-tasting-with-transport-in-italy.a50040821.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Cooking Class in Tuscany](https://mediaim.expedia.com/localexpert/5108581/84ce848e-37a0-48a4-9396-d095086f427b.jpg?impolicy=resizecrop&rw=500&rh=280) ### Cooking Class in Tuscany 3h Free cancellation available CA $410 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.ca/things-to-do/cooking-class.a5108581.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Pizza and Tiramisù Making Class](https://mediaim.expedia.com/localexpert/46351366/618b7358-478b-4574-9f2e-2ca33ee21c71.jpg?impolicy=resizecrop&rw=500&rh=280) ### Pizza and Tiramisù Making Class 4h Free cancellation available CA $188 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/pizza-and-tiramisu-making-class.a46351366.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ### Adventure & outdoor [See all 20 activities](https://expedia.ca/things-to-do/search?&rid=603149&location=Gaiole+in+Chianti&filter.categories=AdventureOutdoor) ![Chianti Wine and Food Safari](https://mediaim.expedia.com/localexpert/562098/7a7087d5-a4b0-4f6b-bddf-f98cef0a4e42.jpg?impolicy=resizecrop&rw=500&rh=280) ### Chianti Wine and Food Safari 10h 10/10 9 reviews Free cancellation available CA $369 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/chianti-wine-and-food-safari.a562098.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Tuscany Hiking Tour from Siena Including Wine Tasting](https://mediaim.expedia.com/localexpert/1139505/e7076e74-fe99-4b02-a9fc-f527a478919b.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tuscany Hiking Tour from Siena Including Wine Tasting 4h Free cancellation available CA $90 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/tuscany-hiking-tour-from-siena-including-wine-tasting.a1139505.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Chianti Wild Safari Adventure through Tuscan Vineyards](https://mediaim.expedia.com/localexpert/48684548/9f0ef7b3-60f3-403a-974f-520e9670c90f.jpg?impolicy=resizecrop&rw=500&rh=280) ### Chianti Wild Safari Adventure through Tuscan Vineyards 4h Free cancellation available CA $179 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/chianti-wild-safari-adventure-through-tuscan-vineyards.a48684548.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![From Florence/Badesse: Chianti quad bike Tour with Wine Tasting](https://mediaim.expedia.com/localexpert/48690613/bd54f0b7-70fd-4b2b-92b2-89dc272305e3.jpg?impolicy=resizecrop&rw=500&rh=280) ### From Florence/Badesse: Chianti quad bike Tour with Wine Tasting 4h Free cancellation available CA $311 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/from-florence-badesse-chianti-quad-bike-tour-with-wine-tasting.a48690613.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Full-Day Chianti Bike Tour from Siena](https://mediaim.expedia.com/localexpert/229287/ccea3909-89dd-49b1-9be4-0e24c8ab251c.jpg?impolicy=resizecrop&rw=500&rh=280) ### Full-Day Chianti Bike Tour from Siena 6h 30m 10/10 2 reviews Free cancellation available CA $213 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/full-day-chianti-bike-tour-from-siena.a229287.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![E-Bike Chianti Small Group Tour from Siena](https://mediaim.expedia.com/localexpert/497709/2f0e6727-d15a-45b1-b38e-ddcb13e0902e.jpg?impolicy=resizecrop&rw=500&rh=280) ### E-Bike Chianti Small Group Tour from Siena 6h Free cancellation available CA $295 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/e-bike-chianti-small-group-tour-from-siena.a497709.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Small Group Guided Hike to Monteriggioni from Siena](https://mediaim.expedia.com/localexpert/232407/0d19fd5d-5e98-42d2-a871-5b1f71a11bec.jpg?impolicy=resizecrop&rw=500&rh=280) ### Small Group Guided Hike to Monteriggioni from Siena 4h 2/10 1 review Free cancellation available CA $90 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/guided-hike-small-group-tour-from-siena.a232407.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Quad Tour quad bike Adventure in Chianti. Lunch and Wine Tasting](https://mediaim.expedia.com/localexpert/3104468/5f23d1bc-d146-46f9-969c-42b9f7b8c06b.jpg?impolicy=resizecrop&rw=500&rh=280) ### Quad Tour quad bike Adventure in Chianti. Lunch and Wine Tasting 8h Free cancellation available CA $524 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/quad-tour-quad-bike-adventure-in-chianti-lunch-and-wine-tasting.a3104468.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Private Taste of Tuscany Tour](https://mediaim.expedia.com/localexpert/49838127/2c8767a9-ec78-45f3-b3ce-7a8ff49db236.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Taste of Tuscany Tour 9h Free cancellation available CA $475 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/private-taste-of-tuscany-tour.a49838127.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Tuscany By E-Bike from Florence](https://mediaim.expedia.com/localexpert/512295/3167280f-d65a-4621-988d-7541b5fe1182.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tuscany By E-Bike from Florence 6h 30m+ 5/10 1 review Free cancellation available CA $246 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/tuscany-by-e-bike-from-florence.a512295.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ### Air, helicopter & balloon tours [See all 5 activities](https://expedia.ca/things-to-do/search?&rid=603149&location=Gaiole+in+Chianti&filter.categories=AirHelicopterBalloonTours) ![Experience the Magic of Tuscany from a Hot Air Balloon](https://mediaim.expedia.com/localexpert/919439/41497245-6034-40ec-8686-1c9c920eaecb.jpg?impolicy=resizecrop&rw=500&rh=280) ### Experience the Magic of Tuscany from a Hot Air Balloon 3h 10/10 1 review Free cancellation available CA $441 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/experience-the-magic-of-tuscany-from-a-hot-air-balloon.a919439.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Hot Air Balloon ride in the Chianti Valley Tuscany](https://mediaim.expedia.com/localexpert/3673792/0b823c84-8830-4664-a4c3-2065b24521e1.jpg?impolicy=resizecrop&rw=500&rh=280) ### Hot Air Balloon ride in the Chianti Valley Tuscany 3h 2/10 1 review Free cancellation available CA $500 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/volo-in-mongolfiera-nella-valle-del-chianti.a3673792.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Hot Air Balloon Flight Over Tuscany from Siena](https://mediaim.expedia.com/localexpert/1153035/74778400-e9be-4eaa-824e-63804a61d910.jpg?impolicy=resizecrop&rw=500&rh=280) ### Hot Air Balloon Flight Over Tuscany from Siena 3h 10/10 1 review Free cancellation available CA $508 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/hot-air-balloon-flight-over-tuscany-from-siena.a1153035.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Siena: Balloon Flight Over Tuscany with a Glass of Wine](https://mediaim.expedia.com/localexpert/44505029/cebd2ada-d125-4c9a-ae6f-655f33f6a6a9.jpg?impolicy=resizecrop&rw=500&rh=280) ### Siena: Balloon Flight Over Tuscany with a Glass of Wine 3h 10/10 1 review Free cancellation available CA $508 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/siena-balloon-flight-over-tuscany-with-a-glass-of-wine.a44505029.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ![Private Tour: Tuscany Hot Air Balloon Flight from Siena](https://mediaim.expedia.com/localexpert/1153043/699d3ae7-cdfb-4cb4-b63e-366d0dd9f0d5.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Tour: Tuscany Hot Air Balloon Flight from Siena 2h 30m Free cancellation available CA $2,949 includes taxes & fees per adult [](https://www.expedia.ca/things-to-do/private-tour-tuscany-hot-air-balloon-flight-with-transport-from-siena.a1153043.activity-details?&rid=603149&location=Gaiole+in+Chianti&swp=off) ## Recommended things to do in Gaiole in Chianti | Number of things to do | 267 | | --- | --- | | 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: Civic Museum and Palazzo Pubblico Entry Ticket](https://expedia.ca/things-to-do/siena-civic-museum-and-palazzo-pubblico-entry-ticket.a50461757.activity-details) - [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) - [Skip the Line: Siena Duomo and City Walking Tour](https://expedia.ca/things-to-do/skip-the-line-siena-duomo-and-city-walking-tour.a1139525.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 | - [Skip the Line: Siena Duomo and City Walking Tour](https://expedia.ca/things-to-do/skip-the-line-siena-duomo-and-city-walking-tour.a1139525.activity-details) - [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) | | With kids | - [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) - [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) - [Skip the Line: Siena Duomo and City Walking Tour](https://expedia.ca/things-to-do/skip-the-line-siena-duomo-and-city-walking-tour.a1139525.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 You can find out about the history of Gaiole in Chianti with a stop at Castle of Brolio. Discover the beautiful countryside and charming coffeehouses 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 walkable 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 walkable 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 quaint 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: Civic Museum and Palazzo Pubblico Entry Ticket](https://expedia.ca/things-to-do/siena-civic-museum-and-palazzo-pubblico-entry-ticket.a50461757.activity-details) > - [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) > - [Skip the Line: Siena Duomo and City Walking Tour](https://expedia.ca/things-to-do/skip-the-line-siena-duomo-and-city-walking-tour.a1139525.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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