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Your Castellina in Chianti Holiday

An easy way to experience this city is with a tailor-made Castellina in Chianti holiday package. Base yourself in the neighbourhood of Badia Coltibuono, which is good for families, nature and walking or go someplace else — our package deals are all about you. If sightseeing is on the cards during your trip to Castellina in Chianti, look around well-known attractions like Isole e Olena Winery, Il Molino di Grace Winery and Castello di Radda Winery. Check out Expedia's wide range of travel options and begin planning your ultimate holiday to Castellina in Chianti now.

Top Castellina in Chianti Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
per person
23 Sept - 28 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
Very small rooms and bathrooms. Breakfast and breakfast staff were awesome and on the top floor. Hotel room small and nothing special. Great location and quiet…but good luck getting out of a car with luggage.

Reviewed on 4 Aug 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on 6 Jun 2025

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
per person
13 Sept - 20 Sept
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.4/10 Exceptional! (104 reviews)
The staff were incredibly kind and helpful. I got a flat tire the day I was leaving the hotel and the staff went above and beyond to help me get the tire fixed so I could be on my way. The hotel is beautiful and the food was excellent. I also requested a more private room and the staff changed the room for me right away. Highly recommended for beauty, serene peace and quiet

Reviewed on 19 Jul 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Save 100% on your flight
per person
7 Sept - 14 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
10/10 Exceptional! (1 review)
Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
per person
6 Oct - 11 Oct
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.8/10 Exceptional! (217 reviews)
AMAZING! Gorgeous! I would recommend to everyone!

Reviewed on 29 Jul 2025

Things to do near Castellina in Chianti

Castellina in Chianti offers a delightful blend of romantic and outdoor activities perfect for a memorable holiday. Visitors can indulge in rejuvenating spa treatments, explore the scenic countryside through cycling and hiking tours, and embark on enchanting trips through the picturesque Chianti region. Whether you seek relaxation or adventure, Castellina in Chianti provides a charming backdrop for your Italian getaway.

Shopping

In Castellina in Chianti, you can enjoy charming local shops for unique gifts and souvenirs. If you're up for a drive, The Mall Luxury Outlet is 29.0km away, offering luxury brands. For a more local vibe, visit Mercato di Sant'Ambrogio, located 33.8km away.

Recreation

Indulge in luxury at the Villa a Sesta Polo Club, just 24.1km from Castellina in Chianti, perfect for a refined retreat. Explore the cosmos at the Chianti Observatory, 6.4km away, or unwind in nature at the Alta Val d'Elsa River Park, located 16.1km from town.

Adventure

Embark on the Sentierelsa Trail for a scenic hike through Tuscany's stunning landscapes, located 12.9km from Castellina in Chianti. Try your hand at karting at the Siena Circuit, 24.1km away, or take a refreshing dip at the Acquacalda Swimming Pool, 14.5km from your base.

Nightlife

For an enjoyable night out in Castellina in Chianti, visit Il Fiaschetto, a charming drinking pub located 25.7km away. With its romantic atmosphere and lively entertainment, it’s the perfect spot to unwind and soak in the local nightlife vibes.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Castellina in Chianti

Castellina in Chianti, a picturesque destination in Tuscany, is ideal for romantic and outdoor getaways. Visitors can explore charming churches, vibrant piazzas, and historic castles, immersing themselves in the rich culture of the Chianti region. Don't miss the opportunity to visit the Castellina fortress and discover the best villas in the area for a truly enchanting experience. This quaint Italian town offers a perfect blend of romance and adventure for every traveller.

  • Piazza del Campo: This iconic square, located 17.7km from Castellina in Chianti, offers a vibrant cultural atmosphere. Renowned for its unique shell shape and stunning medieval architecture, it’s the perfect spot to soak in the local vibes, enjoy a coffee, and watch the world go by.
  • Castello di Albola: Situated 11.3km away, this enchanting castle boasts romantic charm and rich history. Visitors can explore its beautiful vineyards and scenic grounds, while indulging in wine tastings that showcase the region's exceptional produce.
  • Banca Monte dei Paschi di Siena: Located 17.7km from Castellina in Chianti, this historic bank is a testament to Siena's cultural heritage. Its striking architecture and fascinating history make it a compelling stop for those interested in Italy's banking legacy.

Best time to go to Castellina in Chianti

The best time to visit Castellina in Chianti is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is sunny with no rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January40.8°F (4.9°C)Light RainMostly SunnyAverageSlightly Low
February42.8°F (6.0°C)Light RainMostly SunnyAverageSlightly Low
March47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
April54.0°F (12.2°C)Light RainMostly SunnySlightly HighAverage
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 RainSunnySlightly HighAverage
August75.6°F (24.2°C)No RainSunnySlightly HighAverage
September67.1°F (19.5°C)Light RainMostly SunnyAverageSlightly High
October58.5°F (14.7°C)Light RainMostly SunnySlightly LowAverage
November50.0°F (10.0°C)Light RainMostly SunnySlightly LowSlightly Low
December43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage

Tips to save on your trip to Castellina in Chianti

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Castellina in Chianti.
  • Consider traveling to Castellina in Chianti during the low season (January to February and November) for more affordable options.
  • 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.

Castellina in Chianti Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Peretola Airport (FLR)
Population
1,350
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Siena Cathedral, Tenuta Torciano Winery and Cantina Antinori

Top hotels in Castellina in Chianti

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72, Florence, FI
Fully refundable
The price is £84 per night from 24 Aug to 25 Aug
£84
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,102 reviews)
"I had an amazing stay at this hotel. The views from my room were one of the best I've seen in Florence - breathtaking! The staff was incredibly accommodating, and when I mentioned that the airflow in our room was a bit still, they promptly delivered a fan to our room upon my return. The rooftop bar ..."

Reviewed on 4 Aug 2025

The Social Hub Florence Lavagnini
Grand Hotel Baglioni

Grand Hotel Baglioni

4 out of 5
Piazza Unita Italiana 6, Florence, FI
Fully refundableReserve now, pay when you stay
The price is £131 per night from 17 Aug to 18 Aug
£131
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"The rooftop amazing, the staffs, the location everything amazing"

Reviewed on 3 Aug 2025

Grand Hotel Baglioni
c-hotels Ambasciatori

c-hotels Ambasciatori

4 out of 5
Via Luigi Alamanni 3, Florence, FI
Fully refundableReserve now, pay when you stay
The price is £131 per night from 17 Aug to 18 Aug
£131
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
"Good location near train station"

Reviewed on 3 Aug 2025

c-hotels Ambasciatori
See all 15,528 properties in Castellina in Chianti
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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Popular places to visit

Castellina in Chianti which includes farmland

Buondonno Winery

You can enjoy a tasting or tour at Buondonno Winery during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this quaint area.

Buondonno Winery

Archaeological Museum of Chianti

You can browse the exhibits at Archaeological Museum of Chianti, a museum with a story of its own, during your travels to Castellina in Chianti. Discover the beautiful countryside in this walkable area or enjoy its local tours.

Archaeological Museum of Chianti

Castellina Fortress

Learn about the local history of Castellina in Chianti with a stop at Castellina Fortress. Discover the countryside and wineries in this quaint area.

Castellina Fortress

What to do in Castellina in Chianti

Siena: Siena Cathedral and Piccolomini Library Entry Ticket

Siena: Siena Cathedral and Piccolomini Library Entry Ticket

£7
per adult
Siena: Siena Cathedral and Piccolomini Library Entry Ticket
Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

£104
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
Sunny day view of Monteriggioni, a Comune in Italy

Chianti Half Day Wine Tour from Florence

£43
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
See all activities in Castellina in Chianti

Frequently asked questions

Why should I book my Castellina in Chianti holiday with Expedia?
With exceptional-value airfares, hotel and car hire choices all in the same place, Expedia makes booking your Castellina in Chianti adventure hassle-free. What's more, we can help you bundle your bookings into a package holiday so you can get even more savings. Select from wonderful retreats, add your flights and/or a car hire (and maybe even some exciting tours and activities!) and score unbeatable prices. Need to change plans? Expedia has a flexible cancellation policy for many reservations. To find out more, head over to our Customer Service Portal link.
When is the best time of year to holiday in Castellina in Chianti?
Into sightseeing but don't like big crowds? Plan your Castellina in Chianti escape for November, December and January. Typically, it's much quieter than it is in March, May and August. Organise your escape to Castellina in Chianti based on what type of adventure you want. January is the coolest time of year, when daytime temperatures average 4ºC. In July, the warmest period, you'll experience temperatures of around 24ºC during the day.
What are the top hotels for my holiday in Castellina in Chianti?
Many people like to stay at Castello di Fonterutoli Wine Resort in San Leonino. If it's your first visit to Castellina in Chianti, you'll feel right at home here.
How do I get a cheap holiday to Castellina in Chianti?
Our Castellina in Chianti holidays promise plenty of savings for the savvy globetrotter. For the best deals, simply bundle your flights, hotels and extras (such as activities). But bargain prices are only the start of your next epic adventure. When you book with Expedia, and you'll have over 400 airlines and 321,000 properties all over the world to select from. No matter your style or budget, there's a holiday here with your name on it. Learn more about how you can save money on your holiday when you book a flight and hotel together with Expedia.
What should I do on my Castellina in Chianti holiday?
Offering must-visit attractions such as Monteriggioni Castle and Meleto Castle, a holiday in Castellina in Chianti is filled with exciting places to visit. Castello di Radda Winery and Castello di Albola are a couple of other sights also worth exploring.
What is the best area to stay in when on holiday in Castellina in Chianti?
If you plan to visit Buondonno Winery, save yourself the hassle of commuting and book a stay close by. It's one of the most popular attractions in Castellina in Chianti.
Do I need a visa for my Castellina in Chianti holiday?
Official government websites will have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and reason for visiting, whether it be for work or holidays, will determine if you'll need a visa for Castellina in Chianti. Be sure that your passport is up to date and has a minimum of six months validity remaining beyond your date of return. Do all your travel planning well ahead of time to avoid any last-minute surprises.
What should I wear on my Castellina in Chianti holiday?
Do a little research into the sorts of things people in Castellina in Chianti wear, and consider browsing style blogs for some fashion inspiration. Try to create a versatile wardrobe filled with pieces that work for your destination and show off your unique sense of style. Daytime temperatures in January, Castellina in Chianti's coolest month, average 4ºC. July marks this city's warmest month when the average temperature reaches 24ºC. Our top tip? Take the guesswork out of packing and check the local weather conditions.
What does an Expedia Castellina in Chianti holiday include?
Expedia has all you need to lock in your Castellina in Chianti trip, but what your package looks like is entirely up to you. Pick from a combination of hotels, flights and hire cars. In search of some tours or activities to keep you on the move? Once you've made your booking, you can add them too. Whatever your budget or style, there's a package to meet your needs. Explore a large selection of property types and pick one that suits the size of your group. The most popular holiday rentals here are apartments and villas. With Expedia, you can easily tailor your Castellina in Chianti escape any way you want.
Does Expedia offer Book Now, Pay Later Castellina in Chianti holidays?
Expedia has joined forces with online lender Klarna to make your next trip easier on your wallet. Paying in instalments means you can spread the costs of your next big holiday, leaving you with more money to play with while you're away. Klarna has several payment plans to pick from, so you're sure to find one that fits your budget. Browse these flexible payment options:

  • Pay monthly holidays: If paying across multiple transactions is what works best for you, Klarna can help. Paying in convenient monthly instalments will make that dream getaway possible.
  • No-deposit holidays: When you want to jump on an unbeatable deal but don't have the full amount yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your getaway.

Can I choose my airline with a Castellina in Chianti Expedia holiday?
Yes, and with over 400 airlines to pick from all over the world, you're not short on choice. Take a look at the available options and find out which airline suits your needs and budget.

* 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.