Castellina in Chianti

Travel Guide

A stone building with a clock tower, steps leading up to it, and people walking around.
A historic town with medieval architecture, including a prominent tower and closely packed buildings.
A vineyard path with chickens and a white chicken.
A garden with a tree, a building, and a stone wall.
A statue of a clenched fist in front of a stone building with a flag.

High up on a hill in the Tuscan countryside sits this old town with an ancient castle, centuries-old churches and burial sites that date back to Etruscan times.

Castellina in Chianti is an ancient town of cobblestone streets and old buildings. Situated on a hilltop at the crossroads of three valleys, the town has commanding views of the surrounding countryside. Tour historical churches and fortifications, shop in medieval streets and visit burial sites that are more than 2,000 years old.

Discover Castellina's past in the many centuries-old buildings and ancient sites in and around the town. Explore the Rocca Comunale of Castellina, the old fortress that towers over the rest of the town. It houses an archeological museum featuring relics excavated from the local area. See Bronze Age and Etruscan finds, including an Etruscan chariot and medieval artifacts. While you are at the castle, head up the 14th-century tower for views over the town and the surrounding landscape.

Visit the neo-Romanesque Church of San Salvatore, which was rebuilt after the devastation of World War II. Inside is a 15th-century fresco depicting the Virgin Mary with Child. Walk down the Via delle Volte, a covered passageway that skirts the ancient walls and is lined with shops and restaurants.

A short walking distance from the town center is Montecalvario, an Etruscan tomb with four burial chambers. Objects that were found here are now on display in the Museum of Archeology of Chianti Senese at Castellina’s Piazza del Comune. Uncover more history at the Etruscan Necropolis of Poggino, a few minutes’ drive from Castellina. The site features five Etruscan tombs that date back to the 6th century B.C.

Enjoy the town's hospitality in the restaurants on Via Ferruccio, the main street. There are also numerous shops along this street.

Reach Castellina in Chianti’s ancient streets, buildings and archeological sites by bus and train from several other Chianti destinations. Note that the train station is a few miles from the town. The nearest international airport is in FlorenceOpens in a new window, which is 31 miles (49.9 kilometers) north.

Plus Florence - Hostel

Plus Florence - Hostel

Via Santa Caterina D'Alessandria, 15 Florence FI
$112 nightly
The price is $132 total per night from Oct 25 to Oct 26
$132 total
Oct 25 - Oct 26
Total with taxes and fees
Stay at this hostel in Florence. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.6/10 Excellent! (1,002 reviews)
"The rooms were very clean and fresh towels were brought often! The common areas were clean and well maintained. The only thing I wish was there were hooks in both bathrooms (especially the shower) so I could hang my towel and clothes and not have to put them on the floor or the sink. Other than that ..."

Reviewed on Sep 24, 2026

Plus Florence - Hostel
The Social Hub Florence Belfiore

The Social Hub Florence Belfiore

4 out of 5
Viale Belfiore, 55 Florence FI
$131 nightly
The price is $161 total per night from Oct 25 to Oct 26
$161 total
Oct 25 - Oct 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Florence. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Popular attractions Cathedral of Santa ...
The Social Hub Florence Belfiore
The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72 Florence FI
$131 nightly
The price is $160 total per night from Oct 25 to Oct 26
$160 total
Oct 25 - Oct 26
Total with taxes and fees
Book a stay at this business-friendly hotel in Florence. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the breakfast and the pool in ...
The Social Hub Florence Lavagnini
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.
Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills

Siena Tuscany
Book a stay at this family-friendly vacation home in Castellina in Chianti. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Lilliano Estate ...
9.6/10 Exceptional! (82 reviews)
"Wir waren als Familie mit 2 Teenager-Kindern eine gute Woche hier und fanden es super! Das Haus und vorallem der Garten sind traumhaft. Der Pool ist ein paar Schritte entfernt und wird mit anderen geteilt, was völlig okay war. Zum Haus gehört eine Katze, die jeden Morgen an der Terrassentür wartet, ..."

Reviewed on Aug 31, 2026

Villa with large garden in the Chianti hills
Riserva di Fizzano Residence

Riserva di Fizzano Residence

3 out of 5
Localita Fizzano Castellina in Chianti SI
Book a stay at this family-friendly residence in Castellina in Chianti. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Lilliano Estate ...
Riserva di Fizzano Residence
Farmhouse in the heart of the real chiantishire

Farmhouse in the heart of the real chiantishire

Castellina in Chianti Tuscany
Stay at this vacation home in Castellina in Chianti. Enjoy a garden, laundry facilities, and patios. Popular attractions Castellina Fortress and Archaeological ...
Farmhouse in the heart of the real chiantishire
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 Castellina in Chianti attractions

Things to do

Frequently asked questions

Is Castellina in Chianti worth visiting?
Castellina in Chianti is worth visiting for its delicious Italian and European dining. Travelers can also explore standout attractions like the Buondonno Winery, perfect for wine enthusiasts, and the Archaeological Museum of Chianti, which offers a glimpse into the region's rich history.
When is the best time to visit Castellina in Chianti?
The best time to visit Castellina in Chianti is from May through September, when travelers can enjoy warm, sunny weather perfect for exploring the region. For fewer crowds and better value, the quieter months of November through February are a good option, offering cooler temperatures and a more tranquil experience.
What is Castellina in Chianti known for?
Castellina in Chianti is known for its rich history, highlighted by landmarks such as the Castellina Fortress and the Archaeological Museum of Chianti. Travelers can also discover the region's winemaking tradition at places like Buondonno Winery.
What is a good itinerary length for Castellina in Chianti?
A good itinerary length for Castellina in Chianti is one to two days to explore key highlights like Buondonno Winery, the Archaeological Museum of Chianti, and Castellina Fortress. For an extended stay of three to four days, travelers can also enjoy an E-Bike Rental in the Tuscan Hills or an Ape Calessino Tour through Tuscan Landscapes. See Castellina in Chianti Activities.
What are the top things to do in and around Castellina in Chianti?
Castellina in Chianti offers travelers a blend of historical sites, wine experiences, and scenic outdoor adventures:

  • Visit Buondonno Winery for a taste of local wines
  • Explore the Archaeological Museum of Chianti to learn about the region's past
  • Tour the Tuscan landscapes with an Ape Calessino
  • See Castellina Fortress, a historic landmark
  • Rent an E-Bike in the Tuscan Hills for a scenic ride.

How do I plan a trip to Castellina in Chianti?
To plan your trip to Castellina in Chianti, search for places to stay and book flights early. A rental car helps explore attractions like Buondonno Winery or take an Ape Calessino Tour. For outdoor plans, such as e-bike rentals, have indoor options like the Archaeological Museum of Chianti ready for weather flexibility.
What cuisines can you find in Castellina in Chianti?
In Castellina in Chianti you can find Italian cuisine, featuring classic dishes such as fresh pasta, savory pizzas, and hearty regional specialties. Travelers can also explore broader Mediterranean flavors, and enjoy the local wines at the area's wine bars.
Can I book a refundable hotel in Castellina in Chianti?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Castellina in Chianti by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Castellina in Chianti with Expedia?
Expedia makes it easier to plan your Castellina in Chianti trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Castellina in Chianti?
The best choice depends on your travel style. Hotels in Castellina in Chianti can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Castellina in Chianti trip on Expedia?
Once you've booked your Castellina in Chianti trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Castellina in Chianti trip?
Expedia offers customer support before, during, and after your Castellina in Chianti trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Castellina in Chianti?
If it's your first trip to Castellina in Chianti, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Castellina in Chianti hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Castellina in Chianti hotel.

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