Chianti Region Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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

Top Flight + Hotel Deals in Chianti Region

Price found within the past 48 hours. Click for updated prices.
FH55 Hotel Villa Fiesole

FH55 Hotel Villa Fiesole

€390
per person
23 Oct - 25 Oct
found 9 hours ago
Return flight included
Dublin (DUB) to Florence (FLR)
8.8/10 Excellent! (408 reviews)
Dimora Palanca Boutique & SPA

Dimora Palanca Boutique & SPA

Historic Centre of Florence
Save 100% on your flight
€884
per person
17 Oct - 21 Oct
found 1 hour ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9.2/10 Wonderful! (69 reviews)
The accommodation very much complimented our wonderful experience and love for Florence. Our room, the connected amenities and the wonderful attentive service made our trip very memorable.

Reviewed on 7 Sept 2026

Hotel Careggi

Hotel Careggi

Careggi Rifredi
€436
per person
17 Oct - 21 Oct
found 1 hour ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8/10 Very good! (49 reviews)
Clean

Reviewed on 20 Aug 2026

Hotel Cosmopolitan

Hotel Cosmopolitan

€490
per person
17 Oct - 21 Oct
found 1 hour ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
9/10 Wonderful! (1,002 reviews)
Nice hotel close to the airport and reasonably close to the Florence tram.

Reviewed on 6 Sept 2026

NilHotel Florence

NilHotel Florence

€589
per person
17 Oct - 21 Oct
found 1 hour ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.6/10 Excellent! (623 reviews)
Great parking and very clean

Reviewed on 29 Aug 2026

Where to stay in Chianti Region

Find the best Chianti Region areas and neighborhoods for the activities you enjoy most. Learn more about Chianti Region
A rural landscape with vineyards, rolling hills, and scattered houses.

Tavarnelle Val di Pesa

Tavarnelle Val di Pesa is noteworthy for its wineries, and you can make a stop at top attractions like Passignano Abbey and Abbey of Passignano.

A historic stone church with a bell tower, surrounded by well-maintained hedges and a stone wall.

Barberino Val d'Elsa

Barberino Val d'Elsa is noteworthy for its wineries, and you can make a stop at top attractions like Casa Sola - Chianti Winery and Castello di Monsanto.

Default Image

San Donato in Poggio

Travellers like the restaurants in San Donato in Poggio, and Pieve di San Donato in Poggio is a top attraction you might want to visit.

A dilapidated brick structure with a chimney, surrounded by grass and trees.

Certaldo Alto

You'll enjoy the museums and monuments in Certaldo Alto. You might want to make time for a stop at Casa del Boccaccio or Palazzo Pretorio.

Default Image

Sambuca

While Sambuca may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Abbey of Passignano and Passignano Abbey.

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.

*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 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.

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.

Top hotels in Chianti Region

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI
Fully refundableReserve now, pay when you stay
€174
8 Oct - 9 Oct
includes taxes & fees
Villa I Barronci Resort & Spa
Fattoria di Vegi

Fattoria di Vegi

Località Vegi, 16 Castellina in Chianti SI
€298
29 Sept - 30 Sept
includes taxes & fees
10/10 Exceptional! (19 reviews)
"Amazing! I wish I could have stayed forever!"

Reviewed on 4 Sept 2026

Fattoria di Vegi
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

Via Spaltenna 13 Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
€388
5 Oct - 6 Oct
includes taxes & fees
9.6/10 Exceptional! (281 reviews)
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"

Reviewed on 4 Aug 2026

Castello di Spaltenna- Small Luxury Hotels of the World
See all 4,925 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.

Stay near popular Chianti Region attractions

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.
See properties
A grand, illuminated building with arched windows and a central fountain.

The Mall Luxury Outlet

8.8/10 (355 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.
See properties

Tenuta Torciano Winery

9.2/10 (40 reviews)
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.
See properties

Verrazzano Castle

9.8/10 (10 reviews)
You can find out about the history of Greve in Chianti when you stop by Verrazzano Castle. Discover the area's countryside and wineries.
See properties

Castle of Brolio

9.2/10 (44 reviews)
You can find out about the history of Gaiole in Chianti with a visit to Castle of Brolio. Discover the beautiful countryside and wineries in this walkable area.
See properties

Castello di Albola

9.0/10 (9 reviews)
You can enjoy a tasting or tour at Castello di Albola during your travels to Radda in Chianti. Discover the beautiful countryside in this quaint area or enjoy its local tours.
See properties

Meleto Castle

8.6/10 (10 reviews)
Find out about the history of Gaiole in Chianti when you take a trip to Meleto Castle. Discover the beautiful countryside in this walkable area or enjoy its local tours.
See properties

Castello di Radda Winery

9.2/10 (12 reviews)
You can enjoy a tasting or tour at Castello di Radda Winery during your travels to Radda in Chianti. Discover the beautiful countryside in this quaint area or enjoy its local tours.
See properties

What to do in Chianti Region

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

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

€71
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
Michaelangelo's David

Accademia timed-entry Ticket with Instant Delivery & Priority Access

€39
per adult
94% of travellers recommend
Accademia timed-entry Ticket with Instant Delivery & Priority Access
City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

€25
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
See all activities 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 €390. 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.

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.