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Chianti Region Holidays

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Top destinations in Chianti Region

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FlightsHotels

Castellina in Chianti

Castellina in Chianti

The Latest Chianti Region Holiday Packages

Price found within the past 48 hours. Click for updated prices.
  • Interior
    31 Aug - 6 Sept

    Hotel Alessandro Della Spina + Flight

    Pisa City Centre
    6 nights
    3.0 star property
    9.0/10 - Wonderful (768 reviews)
    "The property was well located but the room was very small. There was a bad 'blocked drain smell" in the bathroom and it also affected the bedroom"
    Reviewed July 21, 2026
    Return • Dublin (DUB) - Florence (FLR)
    DUB - FLR • 1 stop FLR - DUB • 1 stop
    €907
    €661
    per traveller
    found 15 hours ago
    Hotel Alessandro Della Spina
  • Exterior
    31 Aug - 6 Sept

    Park Hotel Villa Ariston + Flight

    Camaiore
    5 nights
    4.0 star property
    8.8/10 - Excellent (135 reviews)
    Return • Dublin (DUB) - Florence (FLR)
    DUB - FLR • 1 stop FLR - DUB • 1 stop
    €1,725
    €1,013
    per traveller
    found 22 hours ago
    Park Hotel Villa Ariston
  • Exterior
    31 Aug - 6 Sept

    Hotel Villa Barsanti + Flight

    Pietrasanta
    5 nights
    3.0 star property
    9.2/10 - Wonderful (47 reviews)
    "The hotel was lovely as usual. But most importantly, the staff were top-notch. Everyone at the hotel made it a place to want to come back to. It was a great hotel experience. And we send all the staff a big Gratzie!, Arrividerci. "
    Reviewed July 29, 2023
    Return • Dublin (DUB) - Florence (FLR)
    DUB - FLR • 1 stop FLR - DUB • 1 stop
    €1,081
    €688
    per traveller
    found 22 hours ago
    Hotel Villa Barsanti
  • Room amenity
    31 Aug - 6 Sept

    Mondial Resort & Spa + Flight

    Pietrasanta
    5 nights
    4.0 star property
    8.6/10 - Excellent (137 reviews)
    "The service was excellent. Friendly and helpful staff. The hotel is beautiful and located in a stunning location. The pool was losing tiles which made it look a little rundown. The rooms were cleaned every day and were maintained well, however the rooms were smaller than expected- didn’t bother us too much as we didn’t stay in the room much anyway. Overall, great hotel!"
    Reviewed July 18, 2026
    Return • Dublin (DUB) - Florence (FLR)
    DUB - FLR • 1 stop FLR - DUB • 1 stop
    €1,295
    €873
    per traveller
    found 22 hours ago
    Mondial Resort & Spa
  • Rooftop terrace
    31 Aug - 6 Sept

    Grand Hotel Principe di Piemonte + Flight

    Viareggio
    5 nights
    5.0 star property
    9.6/10 - Exceptional (73 reviews)
    Return • Dublin (DUB) - Florence (FLR)
    DUB - FLR • 1 stop FLR - DUB • 1 stop
    €2,972
    €2,167
    per traveller
    found 22 hours ago
    Grand Hotel Principe di Piemonte

Discover the most popular places to visit in Chianti Region

A spiral staircase with a person standing on it.

Antinori nel Chianti Classico

9.4/10 (16 reviews)
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.

What to do in Chianti Region

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

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

€79
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
See all activities in Chianti Region

Chianti Region Hotel Deals

Snack bar

La Certosa di Pontignano

La Certosa di Pontignano
18.3 km from Chianti Region
9.4 out of 10, Exceptional, (549 reviews)
"Everything was perfect!"
The price is €99
includes taxes & fees
23 Aug - 24 Aug
La Certosa di Pontignano
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.
See all properties in Chianti Region

Frequently Asked Questions

How much does a Chianti Region holiday package cost?

Live it up in Chianti Region from as low as €661. Choose from a wonderful selection of flights, hotels and rental cars to suit your travel style. You can pick up even more discounts when you add a couple of tours or experiences to your package.

How do I get a cheap travel package to Chianti Region?

Find flights that suit your busy schedule, add a hotel to your booking and watch how much you save with a Chianti Region holiday package. It's that easy! From flights and hotels to rental cars and activities, Expedia is your gateway to cheap travel. And with over 550 air carriers and 1,000,000 properties around the world to pick from, you won't be short of choice.

Where should I stay in Chianti Region?

Val dElsa is in the top spot on many Chianti Region must-see lists. Collegiate Church of Santa Maria Assunta is one reason why.

What are the top hotels in Chianti Region?

When it comes to hotels in Val dElsa, Grand Hotel Baglioni and Hotel Spadai are among the favourites. If you're spending time in Greve in Chianti, Hotel Pendini and The Market Urban Hotel will make you feel at home.

How far in advance should I book my Chianti Region holiday?

While prices change from time to time, we generally suggest booking your flight as soon as possible. Many international airfares can be compared on Expedia up to a year in advance. If circumstances have left you booking late, you may still get lucky. Low prices to Chianti Region sometimes emerge only weeks before departure.

What does an Expedia Chianti Region travel package include?

Much of that is up to you. You can pick from a variety of Chianti Region packages, such as a hotel, rental car and flight. You can also book a flight with a hotel, or a flight with a rental car. Once you've made your booking, you can add the fun stuff like experiences and tours. Whatever your perfect Chianti Region holiday looks like, get set to save!

What should I know before booking a Chianti Region travel package?

When you book your flights, hotels and car rentals together, you'll pick up fantastic discounts. Whether you're organising a mountain getaway in a cabin or would rather stay in a fancy hotel in the city, Expedia will help make it happen.

Can I choose my airline with a Chianti Region Expedia holiday package?

Yes — that's one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 partner airlines across the globe, so you have loads of choice when creating your Chianti Region adventure.

If I'm not able to travel, can I cancel my Chianti Region holiday package?

Your situation can change in a flash, so yes. You may be able to cancel or amend your Chianti Region holiday package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still make the necessary changes, but your airline, hotel or car rental company may charge additional fees. Need more information? Look up our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

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Things to do near Chianti Region

The Chianti Region offers a delightful blend of romance and outdoor adventures, making it an ideal destination for tourists. Visitors can indulge in spa treatments, embark on Chianti wine tasting tours, and explore the stunning countryside on foot. Culinary excursions and local tours further enhance the experience, allowing guests to savour the rich flavours and traditions of this enchanting area.

Shopping

In the Chianti Region, indulge in a shopping experience at The Mall Luxury Outlet, located 20.9km away, offering high-end brands. Closer to you, Fashion Groove and Ra-Ma snc, both 19.3km away, present a delightful mix of local fashion and unique gifts for your loved ones.

Recreation

In the Chianti Region, indulge in rejuvenating experiences at the nearby Palasport Mens Sana and Siena Stadium, both offering vibrant sports atmospheres. Visit the Chianti Observatory for a unique family outing, combining entertainment with stargazing in a captivating setting, just a short drive away.

Adventure

Embark on the Sentierelsa Trail for a scenic hike, 22.5km from Chianti, surrounded by breathtaking landscapes. For thrill-seekers, the Saltalbero Adventure Park, 32.2km away, offers exhilarating ziplining experiences. Alternatively, enjoy some adrenaline at the Siena Circuit, located 25.7km from Chianti, perfect for karting enthusiasts.

Nightlife

Chianti Region's nightlife offers a charming mix of romance and entertainment. Visit Il Fiaschetto, a delightful drinking pub just 27.4km away, where you can enjoy a warm atmosphere and unwind with friends over drinks, making for a memorable evening in the heart of Tuscany.

Find the best attractions near Chianti Region

The Chianti Region in Tuscany offers a perfect blend of romance and outdoor entertainment, with captivating attractions such as charming churches, historic castles, and picturesque piazzas. Visitors can immerse themselves in the rich culture and romantic experiences while exploring the renowned Chianti wine region and nearby Florence. This enchanting area is ideal for those seeking a memorable getaway filled with beauty and history.

  • Castello di Radda Winery: Nestled 3.2km from Chianti, this enchanting castle offers a romantic atmosphere surrounded by vineyards. Enjoy wine tastings and explore the rich culture of Tuscany while soaking in stunning views of the landscape.
  • Monteriggioni Castle: Located 13.2km away, this historic palace boasts impressive medieval architecture. Stroll along the ancient walls and immerse yourself in the culture and history of the region, with panoramic views of the surrounding countryside.
  • Medieval Tower of Barbischio: Situated 9.7km from Chianti, this charming tower exudes historical significance and features friendly locals. Engage with the community and discover the fascinating stories behind this medieval landmark.

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.

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.