Chianti Region Holidays from £262

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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.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

Historic Centre of Florence
Save 100% on your flight
£262
per person
3 Dec - 6 Dec
found 4 hours ago
Return flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
We had a wonderful stay at The Moon hotel. The staff are excellent and we had a speedy and very easy check in experience. The Moon is a beautiful, calm place slightly out of the central sights of Florence, but within an easy walk. Our rooms were beautiful. Great showers and the beds were so comfortable. We slept very well. Breakfast was of a high quality, the fresh egg dishes were delicious. If you like cake for breakfast, you will be spoilt for choice. We used the spa area which was lovely at the end of the day. If not included in your room deal it is extra and you need to book a slot. The hydrotherapy pool is not huge, but works well. Sauna and steam room were very good. Overall a wonderful experience and special thanks to Giorgio for his quick check in and excellent and friendly customer service throughout our stay.

Reviewed on 13 Sept 2026

Aurum Firenze

Aurum Firenze

Historic Centre of Florence
Save 100% on your flight
£335
per person
6 Dec - 10 Dec
found 6 hours ago
Return direct flight included
London (LHR) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
The shower in our room was ridiculously small. I am only 5'7 and 178 and had a very hard time just getting in and out . I actually scraped my side getting in yesterday. The floor in the room was dirty and the breakfast was just ok. The breakyvire was spectacular however. there is no way they can advertise this as a 4 star hotel. The restaurant Bondi directly across the street is absolutely phenomenal .

Reviewed on 15 Sept 2026

Aurum Uffizi

Aurum Uffizi

Historic Centre of Florence
Save 100% on your flight
£641
per person
24 Oct - 30 Oct
found 2 days ago
Return flight included
London (LGW) to Florence (FLR)
7.6/10 Good! (1,001 reviews)
Great location

Reviewed on 15 Sept 2026

Relais Uffizi, Tailor made Hotel

Relais Uffizi, Tailor made Hotel

Historic Centre of Florence
Save 100% on your flight
£902
per person
24 Oct - 30 Oct
found 2 days ago
Return flight included
London (LGW) to Florence (FLR)
9.2/10 Wonderful! (161 reviews)
LOVE this hotel! Perfect location, amazing breakfast, fantastic staff, beautiful rooms, excellent bathrooms. Made our Florence trip amazing highlight of our time in Italy!

Reviewed on 15 Sept 2026

Hotel Duomo Firenze

Hotel Duomo Firenze

Historic Centre of Florence
Save 100% on your flight
£422
per person
6 Dec - 10 Dec
found 6 hours ago
Return direct flight included
London (LHR) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)

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 Abbey of Passignano and Passignano Abbey.

Find hotels in Tavarnelle Val di Pesa
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 della Paneretta.

Find hotels in Barberino Val d'Elsa
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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.

Find hotels in San Donato in Poggio
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.

Find hotels in Certaldo Alto
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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.

Find hotels in Sambuca

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

Fattoria di Vegi

Fattoria di Vegi

Località Vegi, 16 Castellina in Chianti SI
£266
9 Oct - 10 Oct
includes taxes & fees
10/10 Exceptional! (24 reviews)
"This place is a little piece of heaven on earth. If you are looking for peace, tranquility, beautiful surroundings, luxurious rooms, friendly hand helpful staff, this is the place for you. We have stayed in many luxurious places, but this hotel we both thought was the best we have ever experienced. ..."

Reviewed on 14 Sept 2026

Fattoria di Vegi
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
£126
15 Oct - 16 Oct
includes taxes & fees
Villa I Barronci Resort & Spa
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
£347
5 Oct - 6 Oct
includes taxes & fees
9.6/10 Exceptional! (286 reviews)
"The experience was exceptional, the dinners in both restaurants on site were spectacular. The staff was amazing, friendly, and made our stay very memorable. We are planning to return soon."

Reviewed on 15 Sept 2026

Castello di Spaltenna- Small Luxury Hotels of the World
See all 4,908 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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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What to do in Chianti Region

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

£21
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine

Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine

£18
per adult
94% of travellers recommend
Florence: Pasta & Tiramisu Cooking Class with Unlimited Wine
Michaelangelo's David

Accademia timed-entry Ticket with App Guide

£33
per adult
90% of travellers recommend
Accademia timed-entry Ticket with App Guide
See all activities in Chianti Region

Frequently asked questions

Why should I book my Chianti Region holiday with Expedia?
Expedia has your back for every detail of your next Chianti Region trip. You'll always land the best deal possible, but when you bundle your flights, hotel and/or car hire into a holiday package, you'll save even more. Want to truly make the most of your break? Add a few exciting tours and activities to your package. Expedia offers flexible cancellation policies on almost all bookings, so there's no need to stress if your travel plans change. Head over to our Customer Service Portal link to learn more.
When is the best time of year to holiday in Chianti Region?
If you enjoy the atmosphere of peak season, head to Chianti Region in May, June and August. If you prefer a calmer vibe, November, December and January are better times to visit. Arrange your escape to Chianti Region based on what style of adventure you're looking for. January is the coolest time of year, when average daytime temperatures are 4ºC. In July, the warmest month, you'll experience temperatures of around 24ºC during the day.
What are the top hotels for my holiday in Chianti Region?
For properties in Val dElsa with cosy beds and friendly service, check out Grand Hotel Duomo and NH Pisa. If you plan to explore Greve in Chianti as well, you'll get a great night's sleep at Hotel Spadai or Grand Hotel Baglioni.
How do I get a cheap holiday to Chianti Region?
Booking a flight and hotel together with Expedia won't just save you time — it'll save you money too. A Chianti Region holiday makes it simple to create the ideal trip. With more than 400 airlines across the world to select from, finding convenient flights that suit your schedule will be no sweat. Not only that, we have over 321,000 hotels globally to choose from. Now that's what you call choice. Whatever your budget, Expedia puts the world within your reach. Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Chianti Region holiday?
Plan your next holiday in Chianti Region around major attractions like Collegiate Church of Santa Maria Assunta and The Mall Luxury Outlet. Many sightseers also recommend Antinori nel Chianti Classico and Tenuta Torciano Winery.
What is the best city to stay in when on holiday in Chianti Region?
Val dElsa is a great base for your holiday. Find a cosy stay here and start exploring this city's best attractions, like Collegiate Church of Santa Maria Assunta.
Do I need a visa for my Chianti Region holiday?
Check the latest information on official government websites. Your nationality and whether you're visiting for work or pleasure will determine if you require a visa for Chianti Region. Get familiar with the application process, including the required documentation, turnaround times and fees. Finalise your application well in advance to allow enough time for processing. Some visas may take weeks or even months to go through, depending on the country.
What should I wear on my Chianti Region holiday?
First, think about the type of activities planned during your trip to Chianti Region and select versatile pieces that you can easily mix and match. For fashion inspiration or information on any dress codes, browse a few style blogs or social media accounts. It's also a smart move to check the weather forecast so you can pack appropriately. July is the warmest month in Chianti Region, with average temperatures of 24ºC. January is when much of this destination is at its coolest, so pack your cases for daily temperatures of around 4ºC.
What does an Expedia Chianti Region holiday include?
With Expedia, you can select any combination of car hires, hotels and flights to create your ideal Chianti Region travel package. Once you've made your booking, simply add on the fun stuff like day tours and activities. Remember — the more you bundle, the more you'll save! Expedia offers a wide array of properties in Chianti Region, giving you the flexibility to tailor-make your holiday. Apartments and villas are two of the most-favoured options for our customers here.
Does Expedia offer Book Now, Pay Later Chianti Region holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in instalments. Simply click on the payment plan that suits best during the checkout process and take away the stress of budgeting for your next trip. Be sure to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:
  • Pay monthly holidays: Klarna offers manageable monthly payment plans that suit all budgets, so you can escape on that well-deserved holiday now.
  • No-deposit holidays: When you want to jump on an awesome deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to secure your getaway.
Can I choose my airline with a Chianti Region Expedia holiday?
Yes — and it's simple too. Expedia has access to more than 400 partner airlines globally. Our packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.

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.