Castellina in Chianti

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.

The quintessential Tuscan hilltop town.

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.

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.

Off-Road Tuscan Wine Private Tour

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

Private Cooking Class with Professional Chef in Castellina in Chianti

Siena and San Gimignano Full-day Private Tour from Castellina

Popular Tour Itineraries Featuring Castellina in Chianti

Name: JayWay Travel Castellina in Chianti Italy Tour Packages
Brand: JayWay Travel
Rating: 4.94 (19 reviews)

Spend some time in Castellina in Chianti on a tour that takes in other cities in Italy and neighboring countries. Our custom tour packages including Castellina in Chianti and other destinations throughout Italy and Europe make multi-city trips 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$4,075 pp^*

A Dream Italian Honeymoon

Rome, Castellina in Chianti, Florence, Venice

10 Days

from$4,475 pp^*

Accessible Italy

Rome, Castellina in Chianti, Florence, Milan

10 Days

from$5,625 pp^*

Italian Highlights

Rome, Castellina in Chianti, Monterosso Al Mare, Venice

11 Days

from$5,100 pp^*

Magical Italian Exploration

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

14 Days

from$6,000 pp^*

* Starting price is per person, in US Dollars, 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.

Glowing Reviews from Our Guests

4.9 / 5

Average of our Guest's Ratings of our trip packages including Castellina in Chianti, based on 19 reviews

Lynn & Evan

California

JayWay make a bespoke trip the best without exceeding your budget!

Year : 2025
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Florence, Venice
Rating :

5 / 5

Joanne, Warren, Frank & Linda

Pennsylvania

JayWay Travel's knowledge of the areas, attention to detail, and selection of excellent providers made our trip such a wonderful experience.

Year : 2025
Visited : Italy
Itinerary : Venice, Florence, Castellina in Chianti, Monterosso Al Mare
Rating :

5 / 5

Pedro, Victoria, Hannah & Hunter

Virginia

JayWay Travel gives you the peace of mind that you will have a well thought out itinerary and a local in country representative that is focused on making sure that your trip is exactly what you are expecting.

Year : 2024
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Florence, Rome
Rating :

5 / 5

Frequently Asked Questions about travel to Castellina in Chianti

What are Castellina's prices like?

Prices in Castellina are generally quite reasonable, especially compared to larger tourist hubs in Tuscany. Meals at local trattorias and restaurants are affordable, with a typical lunch or dinner costing around €15-€30 per person. Attractions like wineries or historical sites typically have entrance fees of €10-€20, though wine tours and tastings may cost a bit more euros.

How can I get around Castellina?

The best way to explore Castellina is on foot, as the town is small and easy to navigate. Cars are only allowed in a few areas of the town, so walking is ideal for discovering its charming streets. If you'd like to visit neighboring areas, we can arrange private transfers If you are staying outside the town and want to explore, renting a car is the best option, as there are no taxis or public transportation available.

Is Castellina safe?

Castellina is very safe.

Does Castellina have options for those with dietary restrictions?

Although Castellina is small, many pizzerias and restaurants offer gluten-free options, and you'll also find plenty of vegetarian choices at most establishments.

How long should I stay in Castellina?

We recommend staying at least two nights in Castellina to fully enjoy the town and its beautiful surrounding nature and vineyards. Adding a third night will allow you for a day trip to explore more of the area.