Title: Visit Castiglion Fiorentino: Best of Castiglion Fiorentino Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Castiglion Fiorentino](https://expedia.ca/Castiglion-Fiorentino-Hotels.d6047858.Travel-Guide-Hotels)[Vacation Rentals in Castiglion Fiorentino](https://expedia.ca/Castiglion-Fiorentino-Vacation-Rentals.d6047858.Travel-Guide-VacationRentals)[Flights to Castiglion Fiorentino](https://expedia.ca/Cheap-Flights-To-Castiglion-Fiorentino.d6047858.Travel-Guide-Flights)[Castiglion Fiorentino Car Rentals](https://expedia.ca/Car-Rentals-In-Castiglion-Fiorentino.d6047858.Car-Rental-Guide)[Castiglion Fiorentino Vacation Packages](https://expedia.ca/Castiglion-Fiorentino.d6047858.Destination-Travel-Guides) # Castiglion Fiorentino ## Travel Guide ![Castiglion Fiorentino](https://images.trvl-media.com/place/6047858/aaab608c-e23c-4d48-acbe-896e0882191d.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Castiglion Fiorentino](https://images.trvl-media.com/place/6047858/389491eb-6e89-483e-8e8b-7e3ba4dbe8fc.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo](https://images.trvl-media.com/place/6047858/389491eb-6e89-483e-8e8b-7e3ba4dbe8fc.jpg) by [Pigellino](https://www.panoramio.com/user/2766323?with_photo_id=22952763) ([Creative Commons Attribution 3.0](https://creativecommons.org/licenses/by/3.0)) ![Castiglion Fiorentino](https://images.trvl-media.com/place/6047858/283772a8-9464-465e-a2df-85ffd89fc89a.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo](https://images.trvl-media.com/place/6047858/283772a8-9464-465e-a2df-85ffd89fc89a.jpg) by [Pigellino](https://www.panoramio.com/user/2766323?with_photo_id=22952763) ([Creative Commons Attribution 3.0](https://creativecommons.org/licenses/by/3.0)) ![Castiglion Fiorentino](https://images.trvl-media.com/place/6047858/63b57006-a405-4117-ac78-986fa8a970ca.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo](https://images.trvl-media.com/place/6047858/63b57006-a405-4117-ac78-986fa8a970ca.jpg) by [Pigellino](https://www.panoramio.com/user/2766323?with_photo_id=22952763) ([Creative Commons Attribution 3.0](https://creativecommons.org/licenses/by/3.0)) ![Castiglion Fiorentino](https://images.trvl-media.com/place/6047858/d7ba7d73-c888-48ed-ad4e-dde6d2a9ceb0.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo](https://images.trvl-media.com/place/6047858/d7ba7d73-c888-48ed-ad4e-dde6d2a9ceb0.jpg) by [Pigellino](https://www.panoramio.com/user/2766323?with_photo_id=22952763) ([Creative Commons Attribution 3.0](https://creativecommons.org/licenses/by/3.0)) ## Visit Castiglion Fiorentino Things to do - Castiglion Fiorentino Hotel Deals - Vacation Rentals in Castiglion Fiorentino ![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/c358cc6c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Villa di Piazzano - Small Luxury Hotel of the World Localita Piazzano, C.P. 6 Cortona AR CA $812 CA $906 total Apr 17 - Apr 18 includes taxes & fees Book a stay at this luxury hotel in Cortona. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ... 9.8/10 Exceptional! (228 reviews) Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly Reviewed on Nov 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=17%2F04%2F2026&endDate=18%2F04%2F2026&selected=971985&PinnedHotelID=971985&HadPinnedHotel=true®ionId=6047858) ![Monastero di Cortona Hotel & Spa](https://images.trvl-media.com/lodging/24000000/23270000/23264500/23264410/b2055c17_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Monastero di Cortona Hotel & Spa Via del Salvatore Cortona AR CA $454 CA $512 total Apr 17 - Apr 18 includes taxes & fees Book a stay at this luxury hotel in Cortona. Enjoy free breakfast, free WiFi, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ... [](https://expedia.ca/Hotel-Search?startDate=17%2F04%2F2026&endDate=18%2F04%2F2026&selected=23264410&PinnedHotelID=23264410&HadPinnedHotel=true®ionId=6047858) ![Hotel Relais II Chiostro di Pienza](https://images.trvl-media.com/lodging/1000000/900000/893100/893017/45dfbbfc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Relais II Chiostro di Pienza Corso Rossellino 26 Pienza SI CA $130 CA $152 total Apr 8 - Apr 9 includes taxes & fees Stay at this hotel in Pienza. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Chiesa ... 8.8/10 Excellent! (635 reviews) A little tired, extremely clean, with an amazing staff Reviewed on Jan 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F04%2F2026&endDate=09%2F04%2F2026&selected=893017&PinnedHotelID=893017&HadPinnedHotel=true®ionId=6047858) [See all 6,515 properties in Castiglion Fiorentino](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=01%2F04%2F2026&endDate=02%2F04%2F2026®ionId=6047858) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino.](https://images.trvl-media.com/lodging/44000000/43500000/43491500/43491483/2d9a5fbe_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Spacious Tuscan Villa with Large Pool near Castiglion Fiorentino. Castiglion Fiorentino Stay at this villa in Castiglion Fiorentino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Agricola Buccelletti Winery and Tennis ... 9.8/10 Exceptional! (38 reviews) Very friendly and accommodating hosts. The meal they cook was excellent. The location was beautiful and the pool area was kept immaculate. It was a characterful and spacious property but some of the furnishings were a little tired and wobbly. The spa bath did not work and neither did the plug in ... Reviewed on Sep 2, 2025 [](https://expedia.ca/Castiglion-Fiorentino-Hotels-NEW-Fenice.h43491483.Hotel-Information) ![Farmhouse in the hills with panoramic view and swimming pool](https://images.trvl-media.com/lodging/19000000/18790000/18782100/18782015/452f0cb7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Farmhouse in the hills with panoramic view and swimming pool Ristonchia Tuscany Book a stay at this family-friendly vacation home in Castiglion Fiorentino. Enjoy private pools, a garden, and laundry facilities. Popular attractions Tennis ... [](https://expedia.ca/Castiglion-Fiorentino-Hotels-Farmhouse-In-The-Hills-With-Panoramic-View-And-Swimming-Pool.h18782015.Hotel-Information) ![Hotel San Gregorio](https://images.trvl-media.com/lodging/3000000/2700000/2692200/2692135/0e5f89fd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel San Gregorio Via Della Madonnina 4 Pienza SI Book a stay at this business-friendly residence in Pienza. Enjoy free WiFi, an outdoor pool, and room service. Popular attractions RI Crea RE and Enoteca Di ... 9.4/10 Exceptional! (139 reviews) A wonderful hotel - great location, friendly staff, comfortable rooms. Reviewed on Mar 25, 2026 [](https://expedia.ca/Pienza-Hotels-Hotel-San-Gregorio.h2692135.Hotel-Information) [See all properties in Castiglion Fiorentino](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6047858&sort=VACATION_RENTAL) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ## Check Castiglion Fiorentino hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6047858&startDate=2026-03-31&endDate=2026-04-01)[Mar 31 - Apr 1](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6047858&startDate=2026-03-31&endDate=2026-04-01) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6047858&startDate=2026-04-01&endDate=2026-03-02)[Apr 1 - Apr 2](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6047858&startDate=2026-04-01&endDate=2026-03-02) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6047858&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026)[Apr 3 - Apr 5](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6047858&startDate=03%2F04%2F2026&endDate=05%2F04%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6047858&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026)[Apr 10 - Apr 12](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6047858&startDate=10%2F04%2F2026&endDate=12%2F04%2F2026) ### Popular places to visit #### Tennis Club Castiglionese Catch an event at Tennis Club Castiglionese during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area. [](https://expedia.ca/Tennis-Club-Castiglionese-Castiglion-Fiorentino.d553248621580159024.Vacation-Attraction) #### Agricola Buccelletti Winery You can enjoy a tasting or tour at Agricola Buccelletti Winery during your travels to La Strada-Santa Cristina. Discover the area's countryside and wineries. [](https://expedia.ca/Agricola-Buccelletti-Winery-Castiglion-Fiorentino.d553248621580159025.Vacation-Attraction) #### Cassero Tower Find out about the history of Castiglion Fiorentino when you spend time at Cassero Tower. You can enjoy the wineries while in the area. [](https://expedia.ca/Cassero-Tower-Castiglion-Fiorentino.d553248621580159023.Vacation-Attraction) #### Archaeological Museum You can browse the exhibits at Archaeological Museum, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area. [](https://expedia.ca/Archaeological-Museum-Castiglion-Fiorentino.d553248621580159022.Vacation-Attraction) #### Vasari Loggia You can find out about the history of Castiglion Fiorentino with a trip to Vasari Loggia. You can enjoy the wineries while in the area. [](https://expedia.ca/Vasari-Loggia-Castiglion-Fiorentino.d553248621580159026.Vacation-Attraction) #### Municipal Art Gallery You can study the exhibits at Municipal Art Gallery, a museum with a storied past, during your trip to Castiglion Fiorentino. You can enjoy the wineries while in the area. [](https://expedia.ca/Municipal-Art-Gallery-Castiglion-Fiorentino.d553248621533001056.Vacation-Attraction) ### Things to do ![Oil museum and oil mill in Tuscany: tour and tasting](https://mediaim.expedia.com/localexpert/47137603/cba72fc6-87d4-4e36-971f-bc6dc0d28c6e.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Oil museum and oil mill in Tuscany: tour and tasting CA $31 per adult [](https://expedia.ca/things-to-do/oil-museum-and-oil-mill-in-tuscany-tour-and-tasting.a47137603.activity-details) ![Montepulciano Wine Tasting in the Tuscan Countryside](https://mediaim.expedia.com/localexpert/50286653/77c79a76-70f1-4375-9739-0f0f71d7da02.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Montepulciano Wine Tasting in the Tuscan Countryside CA $39 per adult [](https://expedia.ca/things-to-do/montepulciano-wine-tasting-in-the-tuscan-countryside.a50286653.activity-details) ![Cellar Tour & Wine Tasting](https://mediaim.expedia.com/localexpert/3097351/68a40ca2-51b5-4652-b05f-599f0a5eb29d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Cellar Tour & Wine Tasting CA $79 per adult [](https://expedia.ca/things-to-do/cellar-tour-wine-tasting.a3097351.activity-details) [See all activities in Castiglion Fiorentino](https://expedia.ca/Things-To-Do-In-Castiglion-Fiorentino.d6047858.Travel-Guide-Activities) ## Cities near Castiglion Fiorentino ![view of medieval town Arezzo, Tuscany, Italy](https://images.trvl-media.com/place/11306/880278d3-d184-4aee-b95b-3e2e82597aa5.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Arezzo ![Cortona](https://images.trvl-media.com/place/601360/f4054673-52dd-4f97-8d57-389d1f349940.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Cortona ![Monte San Savino in provincia di Arezzo](https://images.trvl-media.com/place/6122898/35ec78b5-ca6a-45f3-838c-8e92016f1e8e.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Monte San Savino ![Aerial view of Marciano della Chiana in Tuscany - Italy](https://images.trvl-media.com/place/6285674/d9b72fab-4508-4633-9a73-689cbb64c263.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Marciano della Chiana - Cities near Castiglion Fiorentino - Places of interest [Arezzo](https://expedia.ca/Arezzo.dx11306)[Cortona](https://expedia.ca/Cortona.dx601360)[Monte San Savino](https://expedia.ca/Monte-San-Savino.dx6122898)[Marciano della Chiana](https://expedia.ca/Marciano-Della-Chiana.dx6285674)[La Strada-Santa Cristina](https://expedia.ca/La-Strada-Santa-Cristina.dx6361315)[Creti](https://expedia.ca/Creti.dx3000439377) - [Lake Trasimeno ](https://expedia.ca/Lake-Trasimeno-Umbria.d6055082.Vacation-Attraction) - [Arno River ](https://expedia.ca/Arno-River-Tuscany.d553248621532501484.Vacation-Attraction) - [Piazza Grande ](https://expedia.ca/Piazza-Grande-Arezzo-Centro-Storico.d6104294.Vacation-Attraction) - [Tiber River ](https://expedia.ca/Tiber-River-Marcigliana.d553248621532500472.Vacation-Attraction) - [Pienza Cathedral ](https://expedia.ca/Pienza-Cathedral-Pienza.d6105122.Vacation-Attraction) - [Terme di Montepulciano Spa ](https://expedia.ca/Terme-Di-Montepulciano-Spa-Montepulciano.d6169786.Vacation-Attraction) - [San Donato Hospital ](https://expedia.ca/San-Donato-Hospital-Arezzo.d553248621583444251.Vacation-Attraction) - [Piscine Termali Theia ](https://expedia.ca/Piscine-Termali-Theia-Chianciano-Terme.d553248621555471462.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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