Title: Chianti Region Vacation Packages & Trips 2026 from CA $1,570 | Expedia.ca [Chianti Region Travel Guide](https://expedia.ca/Chianti-Region.dx603148)[Hotels in Chianti Region](https://expedia.ca/Chianti-Region-Hotels.d603148.Travel-Guide-Hotels)[Vacation Rentals in Chianti Region](https://expedia.ca/Chianti-Region-Vacation-Rentals.d603148.Travel-Guide-VacationRentals)[Flights to Chianti Region](https://expedia.ca/Cheap-Flights-To-Chianti-Region.d603148.Travel-Guide-Flights)[Things to do in Chianti Region](https://expedia.ca/Things-To-Do-In-Chianti-Region.d603148.Travel-Guide-Activities)[Chianti Region Car Rentals](https://expedia.ca/Car-Rentals-In-Chianti-Region.d603148.Car-Rental-Guide) ![](https://images.trvl-media.com/place/603148/a6b4be95-df3f-44a2-bf6d-bb1e6f500def.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Chianti Region Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ### Your Chianti Region Vacation Lock in a vacation package to Chianti Region and enjoy what it means to travel on your own terms. You'll be charmed by its walking trails, cycling and views. Start your trip to Chianti Region with some time exploring [San Gimignano](https://www.expedia.ca/San-Gimignano.d11091.Destination-Travel-Guides) visiting popular attractions like Medieval Criminal and Torture Museum and Piazza Duomo. [Gaiole in Chianti](https://www.expedia.ca/Gaiole-In-Chianti.d603149.Destination-Travel-Guides) is another city that draws travellers from near and far. Castello di Albola and Meleto Castle are two of the leading places to see in this destination. If you're ready to stop dreaming and start travelling, Expedia will help turn your Chianti Region vacation into reality. ## Top Chianti Region Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Art Atelier](https://images.trvl-media.com/lodging/5000000/4060000/4053100/4053096/64645dd6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Art Atelier Historic Centre of Florence CA $1,570 per person Mar 8 - Mar 14 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 9.2/10 Wonderful! (1,001 reviews) The room was spacious and the terrace was very nice. The hotel is in walking distance to all the attractions and train station. Reviewed on Jan 6, 2026 ![Il Rivalta - Place of Charme](https://images.trvl-media.com/lodging/46000000/45800000/45790300/45790281/a67d0954_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Il Rivalta - Place of Charme Historic Centre of Florence CA $3,608 per person Feb 14 - Feb 20 found 1 day ago Roundtrip non-stop flight included Hamilton (YHM) to Florence (FLR) 9.2/10 Wonderful! (420 reviews) Excellent hotel with Excellent location and Excellent staff and Excellent rooms Reviewed on Jan 1, 2026 ![Villa Cora](https://images.trvl-media.com/lodging/1000000/30000/22600/22579/bc8037ee_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Villa Cora Oltrarno CA $3,009 per person Mar 22 - Mar 27 found 23 hours ago Roundtrip flight included Toronto (YYZ) to Florence (FLR) 9.8/10 Exceptional! (467 reviews) Nice property and staff. Reviewed on Nov 13, 2025 ![The Moon Boutique Hotel & Spa](https://images.trvl-media.com/lodging/23000000/22260000/22255000/22254976/205f9600_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Moon Boutique Hotel & Spa Historic Centre of Florence CA $1,600 per person Mar 8 - Mar 14 found 1 day ago Roundtrip non-stop flight included Montreal (YUL) to Florence (FLR) 9.6/10 Exceptional! (495 reviews) The spa was wonderful though the jacuzzi could be hotter I think! The only complaint was that the bed wasn’t very comfortable (it was pretty hard) and the pillows were rather flat. Reviewed on Jan 2, 2026 ### Things to do near Chianti Region The Chianti Region in Tuscany, Italy, offers a perfect blend of romance and outdoor adventure. Visitors can indulge in rejuvenating spa treatments and enjoy the beautiful landscapes. A must-do is exploring Chianti through wine tours, which showcase the area’s renowned vineyards. Additionally, consider package tours for a comprehensive experience of Italy's charm and the stunning Chianti countryside. **Shopping** Experience shopping in the Chianti Region at The Mall Luxury Outlet, just 20.9km away, featuring exclusive brands. Ra-Ma snc is a charming store located 19.3km away, perfect for unique finds. Fashion Groove, also 19.3km away, offers a vibrant atmosphere for family-friendly shopping. **Recreation** Experience the wonders of the Chianti Observatory, where family entertainment meets the cosmos, just 9.7km away. Indulge in luxury at the Villa a Sesta Polo Club, 22.5km from the heart of Chianti. For relaxation, explore the serene Alta Val d'Elsa River Park, located 24.1km away. **Adventure** Embark on the Sentierelsa Trail, a scenic hiking experience 22.5km from Chianti Region, where adventure awaits amid breathtaking landscapes. For a thrilling ride, check out the Siena Circuit, a karting venue 25.7km away, perfect for adrenaline enthusiasts. Explore the outdoors with Tuscany MTB Guide, also 22.5km away. **Nightlife** The Chianti Region offers a charming nightlife experience. Visit Il Fiaschetto, a cozy drinking pub located 27.4km away, where you can enjoy a romantic atmosphere filled with entertainment. Sip on local wines and mingle with fellow travellers for a memorable evening in Tuscany. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Find the best attractions near Chianti Region The Chianti Region in Tuscany, Italy, is an enchanting destination perfect for romantic and outdoor vacations. Visitors can explore beautiful churches, castles, and charming piazzas while indulging in the renowned Chianti wines. This area is a cultural haven, offering a mix of city experiences and breathtaking landscapes. Don't miss the chance to tour the famous Chianti vineyards and discover its celebrated wine region, making your trip truly memorable. - **[Monteriggioni Castle: ](https://www.expedia.ca/Monteriggioni-Castle-Monteriggioni.d6258231.Vacation-Attraction)** This historic palace, located 19.3km from the Chianti Region, offers a captivating glimpse into the past with its well-preserved walls and towers. Explore the charming village within, where medieval architecture meets stunning views of the surrounding countryside, providing a truly unique cultural experience. - **[Medieval Tower of Barbischio: ](https://www.expedia.ca/Medieval-Tower-Of-Barbischio-Gaiole-in-Chianti.d6238143.Vacation-Attraction)** Just 9.7km from Chianti, this historic site features an impressive tower that dates back to the medieval era. Its striking architecture and panoramic vistas of the landscape create a sense of stepping back in time, perfect for history enthusiasts. - **[Church of San Sigismondo: ](https://www.expedia.ca/Church-Of-San-Sigismondo-Gaiole-in-Chianti.d6238140.Vacation-Attraction)** Located only 8.0km away, this beautiful church is renowned for its serene atmosphere and artistic elements. Visitors can appreciate the intricate details and local heritage while enjoying the peaceful surroundings of this spiritual landmark. ### Best time to go to Chianti Region The best time to visit Chianti Region can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Chianti Region falls in July, when visitor numbers are moderately high and weather is sunny with no rain. The coolest average temperature around Chianti Region falls in January, visitor numbers are moderately low and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 40.6°F (4.800000000000001°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low | | February | 42.8°F (6.0°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low | | March | 47.5°F (8.6°C) | Light Rain | Mostly Sunny | Average | Average | | April | 54.0°F (12.2°C) | Light Rain | Mostly Sunny | Average | Average | | May | 60.4°F (15.8°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 69.8°F (21.0°C) | Light Rain | Sunny | Average | Slightly High | | July | 75.9°F (24.4°C) | No Rain | Sunny | Moderately High | Average | | August | 75.6°F (24.200000000000003°C) | No Rain | Sunny | Moderately High | Average | | September | 67.1°F (19.5°C) | Light Rain | Mostly Sunny | Moderately High | Slightly High | | October | 58.5°F (14.7°C) | Light Rain | Mostly Sunny | Average | Average | | November | 50.0°F (10.0°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | December | 43.2°F (6.2°C) | Light Rain | Mostly Sunny | Moderately Low | Average | ### Tips to save on your trip to Chianti Region - Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chianti Region. - Consider traveling to Chianti Region during the low season (January to February and November) for more affordable options. - Use the *Price per traveler* filter on Expedia to find a package deal that suits your budget. - Check the *VIP Access properties* filter to discover outstanding hotels with added member perks at select properties. ## Ready to book your vacation to Chianti Region? Choose your dates ## Chianti Region Hotel Deals ![Hotel Ristorante Alcide](https://images.trvl-media.com/lodging/2000000/1410000/1402100/1402058/d779a567_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Ristorante Alcide Viale Marconi, 67/A Poggibonsi SI Fully refundableReserve now, pay when you stay CA $70 CA $77 total Jan 18 - Jan 19 includes taxes & fees 8/10 Very Good! (462 reviews) I highly recommended Reviewed on Oct 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F01%2F2026&endDate=19%2F01%2F2026&selected=1402058&PinnedHotelID=1402058&HadPinnedHotel=true®ionId=603148) ![Hotel Borgo di Cortefreda Relais](https://images.trvl-media.com/lodging/2000000/1220000/1216500/1216478/288cff0c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Borgo di Cortefreda Relais Via Roma 191 Barberino Tavarnelle FI CA $121 CA $142 total Jan 16 - Jan 17 includes taxes & fees 9.4/10 Exceptional! (475 reviews) The hotel and services exceeded my expectations. Reviewed on Nov 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F01%2F2026&endDate=17%2F01%2F2026&selected=1216478&PinnedHotelID=1216478&HadPinnedHotel=true®ionId=603148) ![Villa La Borghetta Resort](https://images.trvl-media.com/lodging/2000000/1590000/1588400/1588342/3a037802_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Villa La Borghetta Resort Via del Cesto Figline e Incisa Valdarno FI Fully refundableReserve now, pay when you stay 7.8/10 Good! (85 reviews) Beautiful experience! Reviewed on Jul 1, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=1588342&PinnedHotelID=1588342&HadPinnedHotel=true®ionId=603148) [](https://expedia.ca/Hotel-Search?startDate=26%2F01%2F2026&endDate=27%2F01%2F2026&selected=1588342&PinnedHotelID=1588342&HadPinnedHotel=true®ionId=603148) [See all 4,765 properties in Chianti Region](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=13%2F01%2F2026&endDate=14%2F01%2F2026®ionId=603148) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Chianti Region ![Castellina in Chianti showing farmland](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/157000/157305-Tuscany.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Buondonno Winery You can enjoy a tasting or tour at Buondonno Winery during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this romantic area. [](https://expedia.ca/Buondonno-Winery-Castellina-in-Chianti.d553248635823420151.Vacation-Attraction) #### Tenuta Torciano Winery You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this relaxing area. [](https://expedia.ca/Tenuta-Torciano-Winery-San-Gimignano.d6252546.Vacation-Attraction) #### Montegufoni Castle Find out about the history of Montegufoni with a stop at Montegufoni Castle. Visit the stunning cathedral and notable monuments in this walkable area. [](https://expedia.ca/Montegufoni-Castle-Montespertoli.d6223322.Vacation-Attraction) ### What to do in Chianti Region ![Florence Accademia Gallery Tour with Entrance Ticket Included](https://mediaim.expedia.com/localexpert/3066485/d26c5e31-1f44-4056-bdee-2fc35c6c6ffc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Florence Accademia Gallery Tour with Entrance Ticket Included CA $61 per adult **92%** of travellers recommend [](https://expedia.ca/things-to-do/florence-accademia-gallery-tour-with-entrance-ticket-included.a3066485.activity-details) ![Pisa and Piazza dei Miracoli Half Day Tour from Florence](https://mediaim.expedia.com/localexpert/558114/ee5005a3-7dc7-4d52-b37b-cb457ae399b1.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Pisa and Piazza dei Miracoli Half Day Tour from Florence CA $50 per adult **88%** of travellers recommend [](https://expedia.ca/things-to-do/pisa-and-piazza-dei-miracoli-half-day-tour-from-florence.a558114.activity-details) ![Micheal Angelo's David](https://mediaim.expedia.com/localexpert/2479829/2bebb71d-abeb-452a-9a00-2b6fddf3b233.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Skip the Line: Florence's Accademia Gallery Priority Entrance Ticket CA $50 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/skip-the-line-florences-accademia-gallery-priority-entrance-ticket.a2479829.activity-details) [See all activities in Chianti Region](https://expedia.ca/things-to-do/search?rid=603148) ## Frequently asked questions ### Can I cancel my flight booking to Chianti Region due to COVID-19? ### What's the best way to find cheap flights to Chianti Region that have flexible change policies? ### What are some of the general tips for travelers to Chianti Region during the COVID-19 outbreak? > - Look into if any restrictions apply to both your destination and origin. You may not be able to travel depending on local circumstances, so make sure you check before you book. > - Wear a face mask even during airport screening. A TSA employee will require you to adjust your mask for ID purposes. > - Avoid handing your boarding pass directly to a TSA officer. Rather, position the pass on the reader and then hold it up for inspection. > - TSA is now allowing passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on bags. This will need to be removed from your bag to be screened. > - To reduce handling during the screening process, place items such as your phone, keys and wallet into your carry-on rather than into the bins. > - If you're taking food through the security checkpoint, place it in a clear plastic bag and then into a screening bin. This lessens the likelihood that a TSA agent will need to touch your carry-on bag or food container for closer inspection. ### Which airlines fly to Chianti Region? ### How can I find cheap tickets to Chianti Region? ### How much is a flight to Chianti Region? ### What are the most popular airports to fly into in Chianti Region? ### When is the cheapest time to fly to Chianti Region? ### How much is a plane ticket to Chianti Region? ### Which airlines with flights to Chianti Region employ COVID-19 cleanliness policies? > - Ryanair - this airline is known for cleaning with disinfectant and providing passenger masks. > - Vueling - this airline is known for providing passenger masks and cleaning with disinfectant. > - Air Dolomiti - this airline is known for cleaning with disinfectant and conducting passenger temperature checks. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - [Badia Coltibuono Hotels ](https://www.expedia.ca/Badia-Coltibuono-Hotels.d553248635975857717.Travel-Guide-Hotels) - 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