Chianti Region Vacations from ¥245,703

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥45,448 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

The Latest Chianti Region Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Eurostars Florence Boutique
Bernini Palace
Villa Cora
Relais Uffizi, Tailor made Hotel
Hotel Duomo Firenze

Find the Best Chianti Region Vacation Packages

Things to do near Chianti Region

Shopping

The Mall Luxury Outlet, located 20.9km from Chianti, offers a blend of luxury brands in a vibrant atmosphere. Nearby, Fashion Groove and Ra-Ma snc, both 19.3km away, provide unique shopping experiences with a mix of local charm and contemporary styles.

Recreation

Chianti Observatory offers a captivating experience under the stars, perfect for families seeking entertainment and wonder. Villa a Sesta Polo Club provides a luxurious retreat with elegant amenities, ideal for relaxation. Palasport Mens Sana caters to sports enthusiasts, featuring facilities for various athletic activities in a vibrant atmosphere.

Adventure

Explore the Sentierelsa Trail for a scenic hike, immersing yourself in the beautiful outdoors, located 22.5km from Chianti. Experience the thrill of karting at the Siena Circuit, situated 25.7km away, and enjoy the adventure vibes. For mountain biking enthusiasts, Tuscany MTB Guide offers fantastic outdoor experiences 22.5km from Chianti.

Nightlife

Experience the vibrant nightlife of the Chianti Region by visiting Il Fiaschetto, a charming drinking pub located 27.4km away. This venue offers a romantic atmosphere filled with entertainment vibes, perfect for relaxing with friends or enjoying a cozy evening out.

*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 is perfect for a romantic outdoor getaway, featuring charming churches, historic castles, and lively piazzas. Explore the stunning Chianti vineyards and discover the famous wine region known for its exceptional wines. Whether you're seeking cultural experiences or a romantic atmosphere, the area's captivating attractions will surely enhance your visit. Don't miss the opportunity to taste the best wines Chianti has to offer while enjoying the beautiful scenery.

  • Passignano Abbey: Nestled 11.3km from the Chianti Region, Passignano Abbey is a serene church steeped in history. The tranquil atmosphere and beautiful architecture invite visitors to explore its rich cultural heritage, making it a perfect spot for reflection and appreciation of medieval art.
  • Palazzo Pubblico: Located 22.5km away, Palazzo Pubblico is a stunning historic palace that showcases exquisite architecture and art. Its vibrant cultural vibes and historical significance make it a captivating destination for those interested in Tuscany's political past and artistic contributions.
  • Fortezza Medicea: Also 22.5km from Chianti, Fortezza Medicea is an impressive historic fort that offers panoramic views of the surrounding landscape. Its architectural grandeur and historical importance provide a fascinating glimpse into the region's defensive strategies and military history.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.6°F (4.800000000000001°C)Light RainMostly SunnyModerately LowSlightly Low
February42.8°F (6.0°C)Light RainMostly SunnyModerately LowSlightly Low
March47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
April54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
May60.4°F (15.8°C)Light RainMostly SunnyAverageSlightly High
June69.8°F (21.0°C)Light RainSunnyAverageSlightly High
July75.9°F (24.4°C)No RainSunnyModerately HighAverage
August75.6°F (24.200000000000003°C)No RainSunnyModerately HighAverage
September67.1°F (19.5°C)Light RainMostly SunnyModerately HighSlightly High
October58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
November50.0°F (10.0°C)Light RainMostly SunnyAverageSlightly Low
December43.2°F (6.2°C)Light RainMostly SunnyModerately LowAverage

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.

Chianti Region Hotel Deals

Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A Poggibonsi SI
Fully refundableReserve now, pay when you stay
The price is ¥8,301 per night from Feb 15 to Feb 16
¥8,301
¥9,131 total
Feb 15 - Feb 16
includes taxes & fees
8/10 Very Good! (462 reviews)
I highly recommended

Reviewed on Oct 14, 2025

Hotel Ristorante Alcide
Villa La Borghetta Resort

Villa La Borghetta Resort

4 out of 5
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

Villa La Borghetta Resort
Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

4 out of 5
Via Roma 191 Barberino Tavarnelle FI
The price is ¥15,136 per night from Feb 8 to Feb 9
¥15,136
¥17,759 total
Feb 8 - Feb 9
includes taxes & fees
9.4/10 Exceptional! (475 reviews)
The hotel and services exceeded my expectations.

Reviewed on Nov 30, 2025

Hotel Borgo di Cortefreda Relais
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.

Discover the most popular places to visit in Chianti Region

What to do in Chianti Region

Frequently asked questions

Can I cancel my flight booking to Chianti Region due to COVID-19?
Our Customer Service Portal is your one-stop shop for almost every travel question, including about flight changes related to COVID-19. For more peace of mind, we suggest looking over the terms and conditions of your preferred airline before reserving a seat.
What's the best way to find cheap flights to Chianti Region that have flexible change policies?
It's as easy as can be with Expedia. Step 1: Type in your travel dates and click the "Search" button. Second step: Check the "No change fee" box below the "Flexible change policies" filter to the left of your screen. Step 3. Reserve your flexible and cheap flight to Chianti Region.
What are some of the general tips for travelers to Chianti Region during the COVID-19 outbreak?
COVID-19 has changed how the world works in countless ways, including how we're able to travel safely. These tips will help you understand these new challenges and prepare you for your trip to Chianti Region:
  • 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?
Alitalia offers flights into or near Chianti Region, including 121 that fly into Peretola Airport (FLR) each month. Select your travel dates and then book your seat early for the biggest bargain.
How can I find cheap tickets to Chianti Region?
To nab a terrific deal to Chianti Region, book well in advance. Also think about using Expedia's handy "flexible dates" link at the top of your search results. This will list prices for similar time frames. In the last seven days, was the best price for a flight to Chianti Region.
How much is a flight to Chianti Region?
One-way flights from () sold for as little as in the last seven days. During this time, the cost of a return air ticket to Chianti Region ranged between and . If you find a fantastic deal, book quickly — these prices don't stick around.
What are the most popular airports to fly into in Chianti Region?
Peretola Airport (FLR) is the main entryway for those headed to Chianti Region. Roughly 1323 flights a month land at this airport.
When is the cheapest time to fly to Chianti Region?
Fly out on a Tuesday to better your chances of securing the cheapest airfare to Chianti Region. Mondays are usually the next most affordable day to depart. Saturday is typically the priciest day to fly anywhere.
How much is a plane ticket to Chianti Region?
In the last seven days, tickets to Chianti Region varied between and . Prices usually rise as your travel date nears, so book a great deal today.
Which airlines with flights to Chianti Region employ COVID-19 cleanliness policies?
As passengers and cabin crew begin traveling again, many airlines have introduced social distancing and other vital measures to reduce the impact of COVID-19. Here are some good examples:
  • 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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.