Chianti Region Holidays

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Your Chianti Region Holiday

Lock in a holiday 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 visiting popular attractions like Medieval Criminal and Torture Museum and Piazza Duomo. Gaiole in Chianti 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 holiday into reality.

Chianti Region Holiday

Chianti Region Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Galileo Galilei Airport (PSA)
Top Sights
Sentierelsa Trail, Castelvecchio Natural Reserve and Valle dellInferno e Bandella

Our pick of the best Chianti Region Hotel Deals

Hotel Toscana Ambassador

Hotel Toscana Ambassador

4 out of 5
Via Salceto, 11 Poggibonsi SI
Fully refundableReserve now, pay when you stay
The price is AU$105 per night from 3 June to 4 June
AU$105
3 June - 4 June
includes taxes & fees
8.2/10 Very Good! (337 reviews)
"several disappointing issues during my stay. The air conditioning was poor — I had to go to the front desk just to get it turned on, and even then it barely worked. The beds were very hard and uncomfortable, and the room had a strange smell that made it less pleasant. On top of that, the walls or ..."

Reviewed on 17 May 2026

Hotel Toscana Ambassador
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13 Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
The price is AU$660 per night from 2 June to 3 June
AU$660
2 June - 3 June
includes taxes & fees
9.6/10 Exceptional! (264 reviews)
"Everything was great, would have like to spend more time here. It’s a bit remote but worth it for peace and quiet."

Reviewed on 15 May 2026

Castello di Spaltenna- Small Luxury Hotels of the World
Relais Vignale & Spa

Relais Vignale & Spa

4 out of 5
Via Pianigiani 9 Radda in Chianti SI
Fully refundableReserve now, pay when you stay
The price is AU$366 per night from 26 May to 27 May
AU$366
26 May - 27 May
includes taxes & fees
9.2/10 Wonderful! (287 reviews)
"My husband and I stayed at Relais Vignale & Spa in Chianti and absolutely loved our experience. The hotel is very romantic, with breathtaking views that made our stay feel extra special. The town itself is peaceful and quiet, which was perfect for a relaxing getaway. The hotel has its own restaurant, ..."

Reviewed on 18 May 2026

Relais Vignale & Spa
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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.
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Discover the most popular places to visit in Chianti Region

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

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

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

Montegufoni Castle

Find out about the history of Montegufoni with a stop at Montegufoni Castle. Visit the notable monuments and stunning cathedral in this walkable area.

Montegufoni Castle

What to do in Chianti Region

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

AU$47
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Small-Group Wine Tasting Experience in the Tuscan Countryside

Small-Group Wine Tasting Experience in the Tuscan Countryside

AU$145
per adult
98% of travellers recommend
Small-Group Wine Tasting Experience in the Tuscan Countryside
Skip-the-Line Duomo: Priority-Access 30-Minute Guided Tour

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

AU$37
per adult
80% of travellers recommend
Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour
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.

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