Castellina in Chianti

Tuscany, Italy

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.

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.

Historic Palazzo in the heart of Castellina

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

Luxury Hotel

A Tuscan hilltop hamlet turned into a luxury 12 room boutique hotel

Boutique Hotel

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

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.

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

Siena and San Gimignano Full-day Private Tour from Castellina

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 make traveling in Central & Eastern Europe hassle-free. We take care of getting you from place to place, accommodation, excursions and activities.

A Week in Central Italy

Rome, Castellina in Chianti, Florence

8 Days

A Dream Italian Honeymoon

Rome, Castellina in Chianti, Florence, Venice

10 Days

Italian Highlights

Rome, Castellina in Chianti, Monterosso Al Mare, Venice

11 Days

Magical Italian Exploration

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

14 Days

Glowing Reviews from Our Guests

4.9 / 5

Average of our Guest's Ratings of our Castellina in Chianti vacation packages

Based on 6 reviews

Mike & Kirsten

Nebraska

JayWay Travel is a company that will take most of the hassles of planning an international trip. From budgeting, preplanning ideas and execution. JayWay Travel help build the trip that you want instead of following someone else's itinerary.

Year : 2019
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Florence, Venice
Rating :

5 / 5

Year : 2019
Visited : Italy
Itinerary : Rome, Castellina in Chianti, Florence, Venice
Rating :

5 / 5

Megan & Jason

Missouri

JayWay Travel turned our dream honeymoon into reality. From help with the accommodations, transfers between cities, daily excursions and so much more, we had the best time. We can’t wait to go on another JayWay vacation.

Year : 2019
Visited : Italy, Croatia
Itinerary : Castellina in Chianti, Rome, Dubrovnik, Hvar, Split
Rating :

4.8 / 5

Year : 2019
Visited : Italy, Croatia
Itinerary : Castellina in Chianti, Rome, Dubrovnik, Hvar, Split
Rating :

4.8 / 5

James & Jan

Texas

JayWay Travel plans your trip down to the smallest detail according to your wishes. Big time travel without the big group.

Year : 2019
Visited : Italy, Slovenia, Croatia
Itinerary : Rome, Castellina in Chianti, Florence, Venice, Ljubljana, Rovinj, Zadar, Split, Korcula, Dubrovnik, Rome
Rating :

5 / 5

Year : 2019
Visited : Italy, Slovenia, Croatia
Itinerary : Rome, Castellina in Chianti, Florence, Venice, Ljubljana, Rovinj, Zadar, Split, Korcula, Dubrovnik, Rome
Rating :

5 / 5