Chianti Region Holidays from £306

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 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

    Packages with flights are ATOL protected

Your Chianti Region Holiday

Make putting together your next amazing adventure a breeze with a holiday package to Chianti Region. If it's walking trails, cycling and views you want to experience, Montevarchi is waiting for you. Begin your trip to Chianti Region with a couple of days in San Gimignano visiting popular attractions like Medieval Criminal and Torture Museum and Piazza Duomo. Radda in Chianti is another city that draws crowds from near and far. Castello di Albola and Meleto Castle are two of the top places to see in this destination. Expedia has everything you need when it comes to planning your Chianti Region holiday. From hotels and flights, to car rentals and more, we know how to create a travel experience like no other.

Top Chianti Region Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotiday Marina di Bibbona

Hotiday Marina di Bibbona

4 out of 5
Save 100% on your flight
Price was £469, price is now £306 per person
£306
per person
25 Apr - 2 May
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
No reviews
Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Price was £1,417, price is now £817 per person
£817
per person
21 May - 26 May
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
8.6/10 Excellent! (483 reviews)
The room was clean and the staff very accommodating. The breakfast was quite sufficient and had a good variety. The location is great. It's a short walk from the square, shopping and from restaurants.

Reviewed on 13 Dec 2025

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Price was £1,167, price is now £770 per person
£770
per person
21 May - 26 May
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
8.8/10 Excellent! (403 reviews)
Staff is wonderful and kind, very accommodating. We stayed here with a lot of family members for our wedding, we got a beautiful spacious suite with the best courtyard views. The rooms are so beautifully designed, the whole villa is just dreamy and true Tuscany. Breakfast is amazing with so many options and so fresh, so delicious! Service is great too. Overall cannot beat the location. We also held our wedding reception dinner here and the food and service and spaces we used were amazing. They even gave us complimentary bottle of champagne and homemade cookies in our room with a lovely note. Overall, we hope to be back!

Reviewed on 25 Nov 2025

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5 out of 5
Save 100% on your flight
Price was £3,387, price is now £2,243 per person
£2,243
per person
20 May - 27 May
found 1 day ago
Return direct flight included
London (LGW) to Florence (FLR)
9.2/10 Wonderful! (192 reviews)
This hotel is absolutely gorgeous. The staff, food and grounds are fantastic. Can’t recommend more! Big thanks to Luka and Giuseppe for making our stay so special. Great wine tasting and delicious wine recommendations. Won’t disappoint

Reviewed on 2 Sept 2025

Residenza Florentia

Residenza Florentia

1 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £921, price is now £612 per person
£612
per person
14 May - 17 May
found 12 hours ago
Return direct flight included
London (LHR) to Florence (FLR)
8.6/10 Excellent! (47 reviews)
Location, accommodations, and communication. Simple but comfortable. A basic facilities, and nice AC, elevator, and luggage storage.

Reviewed on 12 Jun 2025

Things to do near Chianti Region

Discover the enchanting Chianti Region, perfect for a romantic getaway or an adventurous outdoor holiday. Indulge in spa treatments and unwind with body therapies, while exploring the area's renowned Chianti wine and tasting tours. Enjoy leisurely walks through the picturesque landscape, engage in local tours, and savour delectable culinary excursions that highlight the region's rich gastronomic heritage. Experience the charm and beauty of Tuscany in this idyllic setting.

Shopping

The Chianti Region offers delightful shopping experiences such as The Mall Luxury Outlet, located 20.9km away, featuring luxury brands in a vibrant setting. Nearby, Ra-Ma snc and Fashion Groove, both 19.3km away, provide unique local finds in a charming atmosphere perfect for souvenirs.

Recreation

Experience luxury at Villa a Sesta Polo Club, where you can indulge in exclusive amenities amidst serene countryside. For relaxation, the Alta Val d'Elsa River Park offers tranquil nature walks and wellness activities, while the Stadio Artemio Franchi provides an exciting atmosphere for sports enthusiasts.

Adventure

Experience the stunning landscapes of the Chianti Region on Hedonistic Hiking, located 27.4km away, where adventure meets nature. For a thrilling ride, head to the Siena Circuit, 25.7km away, for exhilarating karting. Alternatively, explore the outdoors with Tuscany MTB Guide, situated 22.5km away, perfect for mountain biking enthusiasts.

Nightlife

The Chianti Region offers a vibrant nightlife, with places like Il Fiaschetto, a charming drinking pub located 27.4km away. Enjoy its romantic atmosphere while sipping on delightful drinks and soaking in the lively entertainment that brings the local culture to life.

*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 offers a perfect blend of romance and outdoor adventure, ideal for tourists seeking cultural experiences. Visitors can explore charming churches, historic castles, and lively piazzas, all while indulging in the renowned Chianti wine. With Florence nearby, this picturesque area is a delightful destination for those looking to immerse themselves in the beauty and culture of Tuscany.

  • Meleto Castle: Nestled 9.7km from Chianti, Meleto Castle offers a romantic glimpse into Tuscany's past. Explore its stunning architecture and lush surroundings while soaking up the rich cultural heritage that permeates the castle's walls, making it an enchanting attraction.
  • Church of Santa Maria Assunta: Located 4.8km away, this charming church is a serene spot steeped in history and culture. Its beautiful architecture and tranquil atmosphere provide a perfect setting for reflection and appreciation of local artistry.
  • Piazza del Campo: A vibrant square 22.5km from Chianti, Piazza del Campo is famous for its unique shell shape and lively atmosphere. Experience local events and savour the bustling city vibes while enjoying the surrounding historic buildings.

Best time to go to Chianti Region

The best time to visit Chianti Region is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is sunny with no rain. January is its coolest month on average. At this time, 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

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling during the off-peak season (typically January to February and November) for more affordable package holidays to Chianti Region.
  • 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 Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Galileo Galilei Airport (PSA)

Top hotels in Chianti Region

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 £42 per night from 29 Mar to 30 Mar
£42
29 Mar - 30 Mar
includes taxes & fees
8/10 Very Good! (480 reviews)
I highly recommended

Reviewed on 14 Oct 2025

Hotel Ristorante Alcide
Borgo Vescine

Borgo Vescine

5 out of 5
Località Vescine Radda in Chianti SI
The price is £375 per night from 1 Apr to 2 Apr
£375
1 Apr - 2 Apr
includes taxes & fees
9.4/10 Exceptional! (244 reviews)
You are paying for the view!!!! This hotel was not worth the money spent in my opinion. The hotel staff was not very accommodating, though the restaurant staff was lovely. We had to bring our luggage up to our room and back down during check in and check out — no one even offered and trust me it ...

Reviewed on 5 Oct 2025

Borgo Vescine
Relais Villa Olmo

Relais Villa Olmo

Via Imprunetana Per Tavarnuzze 19 Impruneta FI
The price is £105 per night from 29 Mar to 30 Mar
£105
29 Mar - 30 Mar
includes taxes & fees
Relais Villa Olmo
See all 4,843 properties in Chianti Region
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

A woman on a spiral stairway, part of the modern architecture at Antinori Winery Nel Chianti Classico, San Casciano in Val di Pesa, Tuscany, Italy.

Antinori nel Chianti Classico

4/5(1 review)

You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Visit the stunning cathedral and wineries in this walkable area.

Antinori nel Chianti Classico
Night view of the architecture of the small town of Florence, Shanghai

The Mall Luxury Outlet

4/5(18 reviews)

During your visit to Leccio, you can enjoy retail therapy at The Mall Luxury Outlet. Discover the acclaimed art galleries and stunning cathedral in this walkable area.

The Mall Luxury Outlet

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.

Tenuta Torciano Winery

What to do in Chianti Region

Skip-the-Line Duomo: Priority-Access 30-Minute Guided Tour

Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour

£19
per adult
80% of travellers recommend
Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour
Florence half day combo tour with David, Uffizi & Duomo

Florence Half Day Tour with Michelangelo’s David, Accademia & Uffizi Option

£24
per adult
92% of travellers recommend
Florence Half Day Tour with Michelangelo’s David, Accademia & Uffizi Option
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

£69
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
See all activities 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 travellers 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 travelling 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. Flight-inclusive packages are ATOL protected.