Title: 10 TOP Things to Do in Castelfiorentino October 2025 | Expedia.co.uk [Castelfiorentino Travel Guide](https://expedia.co.uk/Castelfiorentino.dx6047591)[Hotels in Castelfiorentino](https://expedia.co.uk/Castelfiorentino-Hotels.d6047591.Travel-Guide-Hotels)[Flights to Castelfiorentino](https://expedia.co.uk/Cheap-Flights-To-Castelfiorentino.d6047591.Travel-Guide-Flights)[Castelfiorentino Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Castelfiorentino.d6047591.Car-Hire-Guide)[Castelfiorentino Holidays](https://expedia.co.uk/Castelfiorentino.d6047591.Holidays-City-Breaks) # What to do in Castelfiorentino ## Activities, attractions and tours ## Visit Castelfiorentino Types of activities [Castelfiorentino travel guide](https://expedia.co.uk/Castelfiorentino.dx6047591) ![Photo by Vanessa Sgaravizzi](https://mediaim.expedia.com/destination/2/59d02f2e006f53e25180d6cdca5d58f1.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Vanessa Sgaravizzi](https://mediaim.expedia.com/destination/2/59d02f2e006f53e25180d6cdca5d58f1.jpg) ## Castelfiorentino Attractions Let Expedia help you to experience the best that Castelfiorentino has to offer! If you’re planning a trip to Castelfiorentino, 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 to Castelfiorentino 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. #### Places of interest in Castelfiorentino Castelfiorentino is crammed with must-see places to visit and things to do. We can help you decide where to stay in Castelfiorentino, and make it a breeze to explore Castelfiorentino and 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 Castelfiorentino to make sure that you enjoy your holiday 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 to Castelfiorentino, 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 in Castelfiorentino. #### Castelfiorentino attractions Castelfiorentino 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 in Castelfiorentino to keep you entertained. Expedia makes it easy to book your flight, hotel and rental car in advance, making for hassle-free travel and freeing you up to explore the sights of Castelfiorentino. Looking for things to do in Castelfiorentino 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 of Castelfiorentino or catch up with the vibrant local culture, our guides to Castelfiorentino attractions ensure that you’ll have a successful trip, whatever the season. Happy trails! * * * ![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 One Key members save % or more on select activities, hotels, cars and holiday rentals. [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) * * * ### Most fun & popular experiences in Castelfiorentino ### Tours & day trips [See all 117 activities](https://expedia.co.uk/things-to-do/search?&rid=6047591&location=Castelfiorentino&filter.categories=ToursDayTrips) ![Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch](https://mediaim.expedia.com/localexpert/236697/0f88e6e6-ef95-4a56-8618-2b7fc4f041a9.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch 12h 15m 7.8/10 152 reviews Free cancellation available £43 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/tuscany-in-1-day-from-florence-pisa-san-gimignano-siena-with-lunch.a236697.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![San Gimignano, Siena and Chianti - Small Group Tour](https://mediaim.expedia.com/localexpert/321506/80527687-31f8-4be3-9eb8-f949818318b6.jpg?impolicy=resizecrop&rw=500&rh=280) ### San Gimignano, Siena and Chianti - Small Group Tour 9h 8.6/10 285 reviews Free cancellation available £104 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/san-gimignano-siena-and-chianti-small-group-tour.a321506.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Chianti Wineries Tour with Tuscan Lunch and San Gimignano](https://mediaim.expedia.com/localexpert/3066812/0152b205-a96f-450d-b0ae-9ed1784446bc.jpg?impolicy=resizecrop&rw=500&rh=280) ### Chianti Wineries Tour with Tuscan Lunch and San Gimignano 8h 10/10 18 reviews Free cancellation available £167 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/chianti-wineries-tour-with-tuscan-lunch-and-san-gimignano.a3066812.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Tuscany Vespa Tour from Florence with Wine Tasting](https://mediaim.expedia.com/localexpert/3067216/186ed4da-a736-487d-9c27-f55c3c11482c.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tuscany Vespa Tour from Florence with Wine Tasting 8h 10/10 4 reviews Free cancellation available £176 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/tuscany-vespa-tour-from-florence-with-wine-tasting.a3067216.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![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 £236 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/experience-the-magic-of-tuscany-from-a-hot-air-balloon.a919439.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![San Miniato: Wine Tour in a Family-Run Tuscan Winery](https://mediaim.expedia.com/localexpert/48265037/d4056b75-9961-4af8-8fcb-142b4fcb8fa7.jpg?impolicy=resizecrop&rw=500&rh=280) ### San Miniato: Wine Tour in a Family-Run Tuscan Winery 2h 30m 10/10 1 review Free cancellation available £61 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/wine-tour-in-a-family-winery-in-tuscany.a48265037.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Horseback Ride in S.Gimignano with Tuscan Lunch Chianti Tasting](https://mediaim.expedia.com/localexpert/3085681/15f4d4d1-7ea5-4d84-b9e5-7d365dca535e.jpg?impolicy=resizecrop&rw=500&rh=280) ### Horseback Ride in S.Gimignano with Tuscan Lunch Chianti Tasting 8h 10/10 5 reviews Free cancellation available £167 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/horseback-ride-in-s-gimignano-with-tuscan-lunch-chianti-tasting.a3085681.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![San Gimignano, Chianti & Montalcino small group from Siena](https://mediaim.expedia.com/localexpert/228183/fb771371-a28d-414f-b5b8-d4a0e9960158.jpg?impolicy=resizecrop&rw=500&rh=280) ### San Gimignano, Chianti & Montalcino small group from Siena 11h 10/10 2 reviews Free cancellation available £123 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/san-gimignano-chianti-montalcino-small-group-from-siena.a228183.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![San Gimignano: Lunch or Dinner at a Winery with Wine Tasting](https://mediaim.expedia.com/localexpert/47751028/82947172-f2b1-4fa4-b023-d48bf18fd9da.jpg?impolicy=resizecrop&rw=500&rh=280) ### San Gimignano: Lunch or Dinner at a Winery with Wine Tasting 1h 30m Free cancellation available £95 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/san-gimignano-lunch-or-dinner-at-a-winery-with-wine-tasting.a47751028.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience](https://mediaim.expedia.com/localexpert/698109/a06a96d2-88a2-4896-8c26-8a7f8d1fad20.jpg?impolicy=resizecrop&rw=500&rh=280) ### Self-Drive Vintage Fiat 500 Tour from Florence: Tuscan Wine Experience 4h 8.4/10 4 reviews Free cancellation available £118 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/self-drive-vintage-fiat-500-tour-from-florence-tuscan-wine-experience.a698109.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ### Private & custom tours [See all 34 activities](https://expedia.co.uk/things-to-do/search?&rid=6047591&location=Castelfiorentino&filter.categories=Privatecustomtours) ![Farm To table Experience on an organic hilltop estate in Tuscany](https://mediaim.expedia.com/localexpert/50051871/4f1681d7-f14d-4205-a4b0-9a424c7fd1eb.jpg?impolicy=resizecrop&rw=500&rh=280) ### Farm To table Experience on an organic hilltop estate in Tuscany 7h 30m Free cancellation available £151 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/farm-to-table-experience-on-an-organic-hilltop-estate-in-tuscany.a50051871.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Truffle Hunting in Tuscany](https://mediaim.expedia.com/localexpert/3113978/a9f55ec7-b566-49c1-a7df-31ab6ac630ce.jpg?impolicy=resizecrop&rw=500&rh=280) ### Truffle Hunting in Tuscany 8h 10/10 1 review Free cancellation available £334 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/truffle-hunting-in-tuscany.a3113978.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Private Wine & Oil Tasting with Lunch](https://mediaim.expedia.com/localexpert/1097624/5fcd50d5-cbb8-472f-85a1-f7132e12c883.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Wine & Oil Tasting with Lunch 1h 30m Free cancellation available £55 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/vineyard-tour-and-tasting-with-lunch-or-dinner.a1097624.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Private Wine and Extra Virgin Olive Oil Tasting](https://mediaim.expedia.com/localexpert/1097601/2b7e1f23-0721-4c16-903b-f8c9ac963e69.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Wine and Extra Virgin Olive Oil Tasting 45m Free cancellation available £26 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/private-wine-and-extra-virgin-olive-oil-tasting.a1097601.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Private Chianti Tour Half Day 2 Wineries & Lunch in Tuscan Hills](https://mediaim.expedia.com/localexpert/50451425/256baa27-d6ed-455c-9b30-70db2b66eb8f.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Chianti Tour Half Day 2 Wineries & Lunch in Tuscan Hills 4h 30m Free cancellation available £527 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.co.uk/things-to-do/private-chianti-tour-half-day-2-wineries-lunch-in-tuscan-hills.a50451425.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Montelupo Fiorentino: Tuscan Ceramic Master Potter Class](https://mediaim.expedia.com/localexpert/44626190/f673c39c-fade-41fc-8fb1-8995b571d4bf.jpg?impolicy=resizecrop&rw=500&rh=280) ### Montelupo Fiorentino: Tuscan Ceramic Master Potter Class 2h 10/10 1 review Free cancellation available £140 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.co.uk/things-to-do/montelupo-fiorentino-tuscan-ceramic-master-potter-class.a44626190.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Private Day-Trip to Siena and San Gimignano](https://mediaim.expedia.com/localexpert/700800/06f9a81f-6b0a-489c-92a5-9cc8264ca226.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Day-Trip to Siena and San Gimignano 6h Free cancellation available £641 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.co.uk/things-to-do/private-day-trip-to-siena-and-san-gimignano.a700800.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Floren...](https://mediaim.expedia.com/localexpert/5102351/1e4b44eb-f574-438f-82c4-33617708c5d4.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Tuscany Day Tour: San Gimignano and Chianti Wine Region from Floren... 8h Free cancellation available £88 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/private-tuscany-day-tour-san-gimignano-and-chianti-wine-region-from-florence.a5102351.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Private Biodynamic Wines with lunch in Chianti Classico](https://mediaim.expedia.com/localexpert/46301153/ba4108ae-d3dc-49a0-bbbe-02f79943a991.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Biodynamic Wines with lunch in Chianti Classico 5h £299 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.co.uk/things-to-do/biodynamic-chianti-classico-wines-and-focaccia-with-a-sommelier.a46301153.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![San Gimignano - Private Historic Walking Tour](https://mediaim.expedia.com/localexpert/50398247/6d021c1b-2444-453e-a9a0-ce47658ac7ca.jpg?impolicy=resizecrop&rw=500&rh=280) ### San Gimignano - Private Historic Walking Tour 2h £378 includes taxes & fees per traveller\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.co.uk/things-to-do/san-gimignano-private-historic-walking-tour.a50398247.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ### History & culture [See all 31 activities](https://expedia.co.uk/things-to-do/search?&rid=6047591&location=Castelfiorentino&filter.categories=HistoryCulture) ![San Miniato: Wine Tour in a Family-Run Tuscan Winery](https://mediaim.expedia.com/localexpert/48265037/d4056b75-9961-4af8-8fcb-142b4fcb8fa7.jpg?impolicy=resizecrop&rw=500&rh=280) ### San Miniato: Wine Tour in a Family-Run Tuscan Winery 2h 30m 10/10 1 review Free cancellation available £61 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/wine-tour-in-a-family-winery-in-tuscany.a48265037.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![San Gimignano: The Medieval City](https://mediaim.expedia.com/localexpert/4749659/0c82fd0e-a311-4ed2-a43c-ca593f4e12a3.jpg?impolicy=resizecrop&rw=500&rh=280) ### San Gimignano: The Medieval City 2h Free cancellation available £18 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/san-gimignano-the-medieval-city.a4749659.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Vinci: wine-experience among the Tuscan hills](https://mediaim.expedia.com/localexpert/48412185/654e41ff-662a-4f7b-9638-6806ba3aa9eb.jpg?impolicy=resizecrop&rw=500&rh=280) ### Vinci: wine-experience among the Tuscan hills 3h Free cancellation available £31 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/vinci-wine-experience-among-the-tuscan-hills.a48412185.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Horseback Riding with Wine Tour from Florence](https://mediaim.expedia.com/localexpert/5027419/cc949c5b-e1f4-4dc8-93e2-112ab7aa3225.jpg?impolicy=resizecrop&rw=500&rh=280) ### Horseback Riding with Wine Tour from Florence 8h Free cancellation available £167 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/horseback-riding-with-wine-tour-from-florence.a5027419.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Truffle Hunting in Tuscany](https://mediaim.expedia.com/localexpert/3113978/a9f55ec7-b566-49c1-a7df-31ab6ac630ce.jpg?impolicy=resizecrop&rw=500&rh=280) ### Truffle Hunting in Tuscany 8h 10/10 1 review Free cancellation available £334 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/truffle-hunting-in-tuscany.a3113978.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Discover San Miniato](https://mediaim.expedia.com/localexpert/1082748/53a8db42-7a63-4077-87fc-cd4e51dd323c.jpg?impolicy=resizecrop&rw=500&rh=280) ### Discover San Miniato 2h Free cancellation available £32 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/discover-san-miniato.a1082748.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Barberino Tavarnelle: Truffle Hunt Tour with Lunch or Dinner](https://mediaim.expedia.com/localexpert/48107984/1488a9ec-3bef-4232-8441-34d80298e961.jpg?impolicy=resizecrop&rw=500&rh=280) ### Barberino Tavarnelle: Truffle Hunt Tour with Lunch or Dinner 3h Free cancellation available £206 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/barberino-tavarnelle-truffle-hunt-tour-with-lunch-or-dinner.a48107984.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Visit of San Gimignano with local expert guide](https://mediaim.expedia.com/localexpert/46297885/97d0e8c6-7326-4607-aebd-b27913679737.jpg?impolicy=resizecrop&rw=500&rh=280) ### Visit of San Gimignano with local expert guide 2h Free cancellation available £18 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/visit-of-san-gimignano-with-local-expert-guide.a46297885.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Tuscany Jewellery Class - Design and Craft by hand](https://mediaim.expedia.com/localexpert/48041174/d5b0b24f-bdec-4ef6-8f1b-88e7d7952dd1.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tuscany Jewellery Class - Design and Craft by hand 4h Free cancellation available £176 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.co.uk/things-to-do/tuscany-highlight-create-your-own-jewellery-in-an-artclass.a48041174.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![CREMONA private tour: beautiful, historic close to Milan](https://mediaim.expedia.com/localexpert/47814951/87e0c85e-e011-45b1-8c5b-dce1420b9588.jpg?impolicy=resizecrop&rw=500&rh=280) ### CREMONA private tour: beautiful, historic close to Milan 2h Free cancellation available £303 includes taxes & fees per traveller\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.co.uk/things-to-do/cremona-private-tour-beautiful-historic-close-to-milan.a47814951.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ### Adventure & outdoor [See all 6 activities](https://expedia.co.uk/things-to-do/search?&rid=6047591&location=Castelfiorentino&filter.categories=AdventureOutdoor) ![Private Tuscan meal with Wine and EVO oil tasting](https://mediaim.expedia.com/localexpert/1097603/e6a6f35d-6b38-4f32-9777-16145adb7681.jpg?impolicy=resizecrop&rw=500&rh=280) ### Private Tuscan meal with Wine and EVO oil tasting 1h 30m 10/10 1 review Free cancellation available £48 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/vineyard-tour-with-wine-olive-oil-tasting-and-tuscan-meal.a1097603.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Tuscany Private Day Tour from Florence](https://mediaim.expedia.com/localexpert/50750395/52b7999a-b16f-4c52-aec1-efe98175473f.jpg?impolicy=resizecrop&rw=500&rh=280) ### Tuscany Private Day Tour from Florence 10h Free cancellation available £1,132 includes taxes & fees per traveller\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.co.uk/things-to-do/tuscany-private-day-tour-from-florence.a50750395.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Fairways of Elegance: A Premier Golfing Expedition](https://mediaim.expedia.com/localexpert/47132848/824dcd00-4a6d-49b6-b435-688fd48106df.jpg?impolicy=resizecrop&rw=500&rh=280) ### Fairways of Elegance: A Premier Golfing Expedition 5h Free cancellation available £443 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.co.uk/things-to-do/fairways-of-elegance-a-premier-golfing-expedition.a47132848.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![San Gimignano: Bike tour in the Tuscan Hills](https://mediaim.expedia.com/localexpert/48233488/bce0be68-ea33-4b02-85bb-4c4a7591b940.jpg?impolicy=resizecrop&rw=500&rh=280) ### San Gimignano: Bike tour in the Tuscan Hills 4h Free cancellation available £474 includes taxes & fees per adult\* \*Get lower prices by selecting more than 2 adults [](https://www.expedia.co.uk/things-to-do/from-certaldo-bike-tour-in-the-tuscan-hills.a48233488.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Vinci E-bike tour in Leonardo's Chianti](https://mediaim.expedia.com/localexpert/48529439/87bca8d0-e3c6-43d3-9b12-407ac35aeada.jpg?impolicy=resizecrop&rw=500&rh=280) ### Vinci E-bike tour in Leonardo's Chianti 6h Free cancellation available £140 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/vinci-e-bike-tour-in-leonardos-chianti.a48529439.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Explore Chianti's Beauty: E-Bike Tour & Wine Tasting](https://mediaim.expedia.com/localexpert/45716506/d10ae431-1dc0-45af-a410-dd709d50ff7f.jpg?impolicy=resizecrop&rw=500&rh=280) ### Explore Chianti's Beauty: E-Bike Tour & Wine Tasting 4h £114 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/guided-chianti-e-bike-tour-with-wine-tasting.a45716506.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ### Holiday & seasonal tours [See all 5 activities](https://expedia.co.uk/things-to-do/search?&rid=6047591&location=Castelfiorentino&filter.categories=HolidaySeasonalTours) ![Vinci: wine-experience among the Tuscan hills](https://mediaim.expedia.com/localexpert/48412185/654e41ff-662a-4f7b-9638-6806ba3aa9eb.jpg?impolicy=resizecrop&rw=500&rh=280) ### Vinci: wine-experience among the Tuscan hills 3h Free cancellation available £31 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/vinci-wine-experience-among-the-tuscan-hills.a48412185.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![San Gimignano: Dinner in the Winery with Wine Tasting](https://mediaim.expedia.com/localexpert/47677179/31bdd31b-2794-4e96-b7b4-21e4dbea17d0.jpg?impolicy=resizecrop&rw=500&rh=280) ### San Gimignano: Dinner in the Winery with Wine Tasting 1h 30m Free cancellation available £66 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/from-florence-dinner-in-the-winery-with-wine-tasting.a47677179.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Dinner in Winery Garden and Wine Tasting in San Gimignano](https://mediaim.expedia.com/localexpert/47388884/c059a0c6-fb0a-48f4-8949-13d119c07b86.jpg?impolicy=resizecrop&rw=500&rh=280) ### Dinner in Winery Garden and Wine Tasting in San Gimignano 1h 30m £110 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/dinner-in-winery-garden-and-wine-tasting-in-san-gimignano.a47388884.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![From San Gimignano: Chianti Wine tour with 2 wineries](https://mediaim.expedia.com/localexpert/44642727/7a35a83d-3a63-4209-bfbe-6166cbec6bdb.jpg?impolicy=resizecrop&rw=500&rh=280) ### From San Gimignano: Chianti Wine tour with 2 wineries 4h 10/10 1 review Free cancellation available £158 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/from-san-gimignano-half-day-chianti-wine-tour.a44642727.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ![Halloween Dinner Show & Masquerade Ball](https://mediaim.expedia.com/localexpert/50589094/1128b38c-e186-4a4b-8f28-d4d2f833303c.jpg?impolicy=resizecrop&rw=500&rh=280) ### Halloween Dinner Show & Masquerade Ball 5h Free cancellation available £75 includes taxes & fees per adult [](https://www.expedia.co.uk/things-to-do/halloween-dinner-show-masquerade-ball.a50589094.activity-details?&rid=6047591&location=Castelfiorentino&swp=off) ## Recommended things to do in Castelfiorentino | Number of things to do | 146 | | --- | --- | | Cheapest thing to do on Expedia | [San Gimignano: The Medieval City](https://expedia.co.uk/things-to-do/san-gimignano-the-medieval-city.a4749659.activity-details): £18 | | Top 5 things to do | - [Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch](https://expedia.co.uk/things-to-do/tuscany-in-1-day-from-florence-pisa-san-gimignano-siena-with-lunch.a236697.activity-details) - [San Gimignano: The Medieval City](https://expedia.co.uk/things-to-do/san-gimignano-the-medieval-city.a4749659.activity-details) - [San Gimignano, Siena and Chianti - Small Group Tour](https://expedia.co.uk/things-to-do/san-gimignano-siena-and-chianti-small-group-tour.a321506.activity-details) - [Cesani Wine Experience](https://expedia.co.uk/things-to-do/cesani-wine-experience.a3177828.activity-details) - [Visit of San Gimignano with local expert guide](https://expedia.co.uk/things-to-do/visit-of-san-gimignano-with-local-expert-guide.a46297885.activity-details) | | Half-day tours | - [San Gimignano: The Medieval City](https://expedia.co.uk/things-to-do/san-gimignano-the-medieval-city.a4749659.activity-details) - [Cesani Wine Experience](https://expedia.co.uk/things-to-do/cesani-wine-experience.a3177828.activity-details) - [Visit of San Gimignano with local expert guide](https://expedia.co.uk/things-to-do/visit-of-san-gimignano-with-local-expert-guide.a46297885.activity-details) - [Discover San Miniato](https://expedia.co.uk/things-to-do/discover-san-miniato.a1082748.activity-details) - [Private Wine & Oil Tasting with Lunch](https://expedia.co.uk/things-to-do/vineyard-tour-and-tasting-with-lunch-or-dinner.a1097624.activity-details) | | With kids | - [Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch](https://expedia.co.uk/things-to-do/tuscany-in-1-day-from-florence-pisa-san-gimignano-siena-with-lunch.a236697.activity-details) - [San Gimignano: The Medieval City](https://expedia.co.uk/things-to-do/san-gimignano-the-medieval-city.a4749659.activity-details) - [San Gimignano, Siena and Chianti - Small Group Tour](https://expedia.co.uk/things-to-do/san-gimignano-siena-and-chianti-small-group-tour.a321506.activity-details) - [Cesani Wine Experience](https://expedia.co.uk/things-to-do/cesani-wine-experience.a3177828.activity-details) - [Discover San Miniato](https://expedia.co.uk/things-to-do/discover-san-miniato.a1082748.activity-details) | ## What to do in Castelfiorentino * * * ### Popular places to visit #### Castle of Oliveto You can learn about the history of Castelfiorentino with a stop at Castle of Oliveto. Discover the beautiful countryside and wineries in this relaxing area. [](https://expedia.co.uk/Castle-Of-Oliveto-Castelfiorentino.d553248621562141307.Attraction) #### Castello di Coiano You can enjoy a tasting or tour at Castello di Coiano during your travels to Coiano. [](https://expedia.co.uk/Castello-Di-Coiano-Castelfiorentino.d873868520440705024.Attraction) #### Benozzo Gozzoli Museum You can spend an afternoon browsing the exhibits at Benozzo Gozzoli Museum during your trip to Castelfiorentino. Discover the beautiful countryside and wineries in this quaint area. [](https://expedia.co.uk/Benozzo-Gozzoli-Museum-Castelfiorentino.d553248621562141305.Attraction) #### Teatro del Popolo You can get tickets for a performance at Teatro del Popolo on your trip to Castelfiorentino. Discover the beautiful countryside and wineries in this quaint area. [](https://expedia.co.uk/Teatro-Del-Popolo-Castelfiorentino.d553248621532498364.Attraction) * * * Looking for fun things to do nearby? Check [things to do near me](https://www.expedia.co.uk/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 Castelfiorentino ![Gambassi Terme](https://mediaim.expedia.com/destination/1/f9c4a8df4703f7f002959cd2881c01a7.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Gambassi Terme [](https://expedia.co.uk/Gambassi-Terme.dx602568) ![Photo by Paula Warren](https://mediaim.expedia.com/destination/2/211129243aee2727f1616484c1e71916.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Montespertoli [](https://expedia.co.uk/Montespertoli.dx602588) ![Montaione](https://mediaim.expedia.com/destination/1/b8049a9a991acd27eaa075fe5c6454f3.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Montaione [](https://expedia.co.uk/Montaione.dx602919) ![Certaldo](https://mediaim.expedia.com/destination/1/2bb4ff275e0a279c98eb08f6ff137816.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Certaldo [](https://expedia.co.uk/Certaldo.dx603153) ![Empoli](https://mediaim.expedia.com/destination/1/4e48901155694ea587658e1f40b7f3a3.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Empoli [](https://expedia.co.uk/Empoli.dx6069671) ![Photo by Antonio Torrisi](https://mediaim.expedia.com/destination/2/778e5ada3967e77f92efb7ec7c893b8e.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### San Miniato [](https://expedia.co.uk/San-Miniato.dx6123917) ## Frequently asked questions ### Is Castelfiorentino worth visiting? > One of the most common things to do in Castelfiorentino is explore Montegufoni Castle. Check this top sight off your itinerary, then discover more of the area's bars and pubs and walking trails. ### How do I spend a day in Castelfiorentino? > Kick-start your day with a visit to Montegufoni Castle and Castello Sonnino. Then, explore different parts of Castelfiorentino for local dining and a little retail therapy. ### What is the top tourist attraction in Castelfiorentino? > The top tourist attraction in Castelfiorentino is Montegufoni Castle, so make sure to add it to your agenda. ### Is three days enough to stay in Castelfiorentino? > You can easily enjoy leading attractions like Agricola Tamburini Emanuela, Castello Sonnino and Palazzo Pretorio with a three-day break in Castelfiorentino. On average, many travellers book two days here. There's plenty to experience nearby too, so linger longer and venture to Florence. ### Is Castelfiorentino a walkable city? > If discovering on foot sounds like your kind of holiday, Castelfiorentino is an ideal destination. Find leading sights, such as Teatro del Popolo, a walkable distance from downtown. You can also go for a stroll around Case Nuove, a vibrant neighbourhood located about 3 kms (2 miles) from downtown. ### What are some activities to do in Castelfiorentino with kids? > Deciding what to do in Castelfiorentino with kids has never been simpler. Whether you have teenagers or toddlers, there's a range of family-friendly activities to keep everyone busy here. > > > > - [Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch](https://expedia.co.uk/things-to-do/tuscany-in-1-day-from-florence-pisa-san-gimignano-siena-with-lunch.a236697.activity-details) > - [San Gimignano: The Medieval City](https://expedia.co.uk/things-to-do/san-gimignano-the-medieval-city.a4749659.activity-details) > - [San Gimignano, Siena and Chianti - Small Group Tour](https://expedia.co.uk/things-to-do/san-gimignano-siena-and-chianti-small-group-tour.a321506.activity-details) > - [Cesani Wine Experience](https://expedia.co.uk/things-to-do/cesani-wine-experience.a3177828.activity-details) > - [Discover San Miniato](https://expedia.co.uk/things-to-do/discover-san-miniato.a1082748.activity-details) ### What to do in Castelfiorentino for adults? > Agricola Tamburini Emanuela and Tenuta Barbadoro are just a couple of the things to do in Castelfiorentino. With plenty of activities available, there's something here for everyone to experience. ### Are there free things to do in Castelfiorentino? > One of the simplest ways to learn about free things to do in Castelfiorentino is to ask a local tour guide. You'll get insider recommendations on cool neighbourhoods, parks and other attractions you can enjoy without reaching for your wallet. Church of Saint Jacob and Saint Philip is one place that doesn't charge an entrance fee. ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Other - [2 Star Hotels in Empolese Val d'Elsa](https://www.expedia.co.uk/2Star-Empolese-Val-DElsa-Hotels.s20-0-d6131291.Travel-Guide-Filter-Hotels) - [Alberi Hotels](https://www.expedia.co.uk/Alberi-Hotels.d553248635975858182.Travel-Guide-Hotels) - [Brusciana Hotels](https://www.expedia.co.uk/Brusciana-Hotels.d6342147.Travel-Guide-Hotels) - [Hotels with Gym in Castelfalfi](https://www.expedia.co.uk/Castelfalfi-Hotels-Hotel-With-Gym.0-0-d553248623000843183-thotelwithgym.Travel-Guide-Filter-Hotels) - [Castelfalfi Hotels](https://www.expedia.co.uk/Castelfalfi-Hotels.d553248623000843183.Travel-Guide-Hotels) - [Certaldo Alto Hotels](https://www.expedia.co.uk/Certaldo-Alto-Certaldo-Hotels.0-n6223743-0.Travel-Guide-Filter-Hotels) - [Beach Resorts & in Certaldo](https://www.expedia.co.uk/Certaldo-Hotels-Beach-Hotels.0-0-d603153-tBeachHotels.Travel-Guide-Filter-Hotels) - 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