Chianti Region Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 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

Chianti Region Holiday

Things to do near Chianti Region

Experience the romantic charm of the Chianti Region in Tuscany, perfect for outdoor adventures and entertainment. Enjoy rejuvenating spa treatments, explore the scenic SentierElsa trail, and indulge in delightful picnics. Don't miss out on immersive Chianti tours that showcase the region's stunning landscapes and rich culture. Make the most of your time in Tuscany by visiting its captivating tourist destinations for an unforgettable holiday.

Shopping

Experience shopping in the Chianti Region with a visit to The Mall Luxury Outlet, 20.9km away, offering luxury brands amid a vibrant atmosphere. Ra-Ma snc, located 19.3km away, is perfect for unique gifts, while Fashion Groove, also 19.3km away, combines family-friendly vibes with great shopping.

Recreation

Villa a Sesta Polo Club offers a luxurious countryside retreat with stunning landscapes and equestrian activities, perfect for relaxation. For sports enthusiasts, Siena Stadium and Stadio Artemio Franchi provide thrilling matches and vibrant atmospheres, allowing you to immerse yourself in Italy's sporting culture.

Adventure

The Sentierelsa Trail offers a fantastic hiking experience, set 22.5km from Chianti Region, with stunning scenery and outdoor adventure vibes. For a thrilling ride, the Siena Circuit karting, located 25.7km away, lets you unleash your competitive spirit in a fun environment. Enjoy the Tuscany MTB Guide for outdoor cycling adventures, also 22.5km away.

Nightlife

Experience the enchanting Chianti nightlife by visiting the Chianti Observatory for stellar views, or enjoy culture and romance at the Vittorio Alfieri Theater. For more cosmic vibes, head to the Arcetri Observatory, where entertainment awaits under the stars, all within easy reach from the region.

*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 getaway filled with entertainment and outdoor activities. Explore charming villages, historic churches, and majestic castles while soaking in the stunning Chianti hills and renowned wine district. This region offers a wealth of cultural experiences, making it ideal for those seeking romance and adventure. Don't miss the lovely piazzas and local attractions that truly capture the essence of Chianti.

  • Castello di Albola: Nestled 3.2km from Chianti Region, this enchanting castle offers a romantic atmosphere steeped in culture. Explore its stunning architecture and indulge in wine tasting from the estate's vineyards.
  • Piazza Matteotti: Located 8.0km away, this vibrant square buzzes with city vibes and cultural charm. Enjoy the lively cafés, local markets, and beautiful architecture that make it a perfect spot for people-watching.
  • Church of Santa Maria Assunta: Just 4.8km from Chianti Region, this historic church showcases remarkable art and architecture. Its serene atmosphere invites reflection and appreciation of its cultural significance.

Best time to go to Chianti Region

The best time to visit Chianti Region is dependant 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

Booking tips and Expedia advantages for Chianti Region

To save money while visiting the Chianti Region, plan your trip for January, February, or November when prices are lower. Book accommodation about a month in advance, and consider last-minute deals on Expedia. Mondays are the most economical days to stay, while Fridays tend to be pricier. Use Expedia's search tool to filter by budget and eco-friendly options. Look for package deals that combine flights and activities for additional savings. Enjoy free activities like vineyard walks and local markets to immerse yourself in the region without breaking the bank.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Chianti Region are January to February and November, where the prices are slightly lower. This is in comparison to May to June and September, where prices are slightly higher.
  • The best time to book a hotel: The cheapest time to book a hotel around Chianti Region is usually 1 month out from when you are planning to stay, though if you're late to the party, have a look at Expedia's last minute deals - the green banner below the hotel's price indicates a discounted rate.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Chianti Region is Monday. The most expensive day to stay around Chianti Region is Friday.
  • Find cheap hotels on Expedia: Expedia’s search tool enables you to set your budget, choose your desired location, and much more. You can easily organise your results to display prices from lowest to highest, allowing you to find the most affordable accommodation first. Additionally, you can refine your choices by hotel type; for instance, selecting the “Eco-certified” filter will showcase sustainable and environmentally-friendly hotels that you can book.
  • Consider bundling your trip: You might find that you can save some money by combining your hotel stay in the Chianti Region with your flights and activities through an Expedia package deal.

Our pick of the best 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 NZ$93 per night from 23 Nov to 24 Nov
NZ$93
23 Nov - 24 Nov
includes taxes & fees
8/10 Very Good! (459 reviews)
I highly recommended

Reviewed on 14 Oct 2025

Hotel Ristorante Alcide
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
9.4/10 Exceptional! (259 reviews)
All good

Reviewed on 20 Oct 2025

Get rates
Castello di Spaltenna- Small Luxury Hotels of the World
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 1 July 2025

Get rates
Villa La Borghetta Resort
See all 4,945 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.

Discover the most popular places to visit in Chianti Region

Antinori nel Chianti Classico

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

Antinori nel Chianti Classico

The Mall Luxury Outlet

4/5(8 reviews)

During your visit to Reggello, 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 quaint area.

Tenuta Torciano Winery

What to do in Chianti Region

Florence Accademia Gallery Tour with Entrance Ticket Included

Florence Accademia Gallery Tour with Entrance Ticket Included

NZ$76
per adult
90% of travellers recommend
Florence Accademia Gallery Tour with Entrance Ticket Included
Skip-the-Line Duomo: Priority-Access 30-Minute Guided Tour

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

NZ$43
per adult
78% of travellers recommend
Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour
Cooking Art Brunelleschi

Cooking Art Brunelleschi

NZ$120
per adult
Cooking Art Brunelleschi
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.

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