Castellina in Chianti

The quintessential Tuscan hilltop town.

We have chosen Castellina as one of our key destinations in Tuscany as this small town offers all the facilities most visitors need, while allowing them to enjoy the countryside. Public transport is limited, so you will definitely need a driver or rental car while you're here. On the edge of a village is a Vespa and Cinquecento (vintage Fiat car) rental company, should you want to indulge in a little nostalgic exploration of the surroundings. Close by you'll find San Gimignano, a "medieval Manhattan" well worthy of a day trip, and the walled town of Monteriggioni is even closer.

Whether you choose to go wandering in the countryside – there are some nice trails nearby – or visit Tuscany's major towns like Florence and Siena, you'll love coming back "home" to Castellina. This is the heart of wine country and the fruit of the vine is a big part of the culture here. With a choice of eateries from basic pizzeria to fine dining, and one of our favorite gelaterias of all time, Castellina's got a lot to like.

Popular Tour Itineraries Featuring Castellina in Chianti

Spend some time in Castellina in Chianti on a tour that takes in other cities in Italy and neighboring countries. Our vacation packages including Castellina in Chianti and other destinations throughout Italy and Europe hassle-free. We take care of getting you from place to place, accommodation, excursions and activities.

A Week in Rome & Tuscany

Rome, Castellina in Chianti, Florence

8 Days

from$3,375^*

A Dream Italian Honeymoon

Rome, Castellina in Chianti, Florence, Venice

10 Days

from$3,850^*

Accessible Italy

Rome, Castellina in Chianti, Florence, Milan

10 Days

from$5,050^*

Italian Highlights

Rome, Castellina in Chianti, Monterosso Al Mare, Venice

11 Days

from$4,475^*

Magical Italian Exploration

Rome, Positano, Florence, Castellina in Chianti, Florence, Venice

14 Days

from$5,300^*

* Starting price is based on double occupancy in 3 star accommodation, in the most affordable month an itinerary is offered. Airfare to Europe is not included.

Click on your choice of itinerary, select number of travelers in your party, month of travel, and desired star level of accommodation to get an approximate price. Submit the enquiry form with any additional details and we can start planning your customized trip.

Where to stay in Castellina in Chianti

As one of the larger villages in Chianti, Castellina makes for a great base. With its centuries of history there are some spectacular properties to stay in. Take you pick from farmhouses, palazzos and converted medieval hamlets.

Central Historical Palazzo

A luxurious place of real elegance where you can get in touch with the beautiful culture of the Italian countryside.

Design Boutique Hotel

A luxurious hotel in the hills, with great amenities and beautiful surroundings.

Luxury Boutique Hotel

A Tuscan hilltop hamlet turned into a luxury 17 room boutique hotel.

Things to do in Castellina in Chianti

We've got a broad range of city tours, day trips and excursions to keep you busy in Castellina in Chianti. This charming town makes for a calm base from which to explore surrounding Tuscany. Spend a private day trip exploring the Val d'Orcia, visiting Montalcino, Montepulciano and Pienza, or head to Siena (and perhaps also San Gimignano). You can also stay in town for a tasting dinner, or private cooking class with a professional local chef. When we send you your customized itinerary you will be able to choose additional excursions to include in your vacation package or consider adding later.

Private Cooking Class with Professional Chef in Castellina in Chianti

Val d'Orcia Private Day Trip: Montalcino, Montepulciano and Pienza from Castellina in Chianti

Off-Road Tuscan Wine Private Tour

Siena and San Gimignano Full-day Private Tour from Castellina

Glowing Reviews from Our Guests

4.9 / 5

Average of our Guest's Ratings of our trip packages including Castellina in Chianti, based on 14 reviews

Ali, Marguerite, Paula & Amy

New Jersey

JayWay was easy to work with, had great ideas and were very responsive. We always felt taken care of and their contacts are top-notch!

Year : 2023
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Rome
Rating :

4.8 / 5

Kristin, Robert, Cassidy & Casey

The trip was FAN tastic! It really was all I'd hoped it would be and every single one of us enjoyed every minute of it.

Year : 2023
Visited : Italy
Itinerary : Rome, Florence, Castellina in Chianti, Florence, Naples, Ravello, Positano, Naples
Rating :

5 / 5

Deborah & Richard

California

It was excellent. Jay was so kind and asked us what was our interest for the trip. Both Daniela and Nikoleta were excellent and so thoughtful. They both helped us out whenever we needed help. We've used other agencies in the past, but JayWay by far is superior to the others.

Year : 2023
Visited : Italy, Slovenia, Croatia
Itinerary : Naples, Rome, Castellina in Chianti, Florence, Venice, Ljubljana, Rovinj, Plitvice, Split, Hvar, Dubrovnik
Rating :

5 / 5

Frequently Asked Questions about travel to Castellina in Chianti

What are Castellina's prices like?

In the center, a quick lunch with a drink costs around 25 euros. Museums and landmarks generally cost 10-20 euros. For a full dinner, budget at least 30-40 euros.

How can I get around Castellina?

The best way to explore Castellina's center is by foot. If you'd like to visit neighboring areas, we can arrange private transfers, or you can rent a Fiat 500 from the town's only car rental provider.

Is Castellina safe?

Castellina is very safe.

Does Castellina have options for those with dietary restrictions?

Although Castellina is quite small, some pizzarias and restaurants offer gluten-free options, and you can also find many vegetarian options in most restaurants.

How long should I stay in Castellina?

We suggest spending at least two nights in Castellina, in order to enjoy both the town and the beautiful nature and vineyards surrounding it. Consider adding a third night to make room for a day trip.