Castellina in Chianti Vacations and Tours - JayWay Travel
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Tuscany

  | Italy
The quintessential Tuscan hilltop town
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Make Tuscany the first stop on your trip.

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Tuscany Sights

We have chosen Castellina as one of our key destinations in Tuscany as this small town or large village offers all the facilities most visitors need while allowing them to enjoy the countryside location as well. 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.

Tuscany Tourism

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.

"Jayway Travel is an excellent option for those who are looking for guidance with a difficult-to-plan vacation but aren't interested in group or guided tours. Having on-the-ground experts available and reachable via a provided cell phone is an extremely valuable offering that is difficult to find with other tour companies."

Elizabeth & Scott

Elizabeth & Scott

District of Columbia

"The trip went so smoothly it was the most perfect honeymoon. Everyone we met and/or assisted in planning our trip was very helpful. JayWay gave us excellent customer service, fantastic accommodation, and a great vacation at a great price."

Anita & Matt

Anita & Matt

Chicago, IL

Where to stay in Tuscany

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.


Bettina
Central Europe Destination Manager

What I love about Tuscany...

“Tuscany is heaven, I am always happy to go back and spend a longer time there and really feel the essence of that beautiful region. Tuscany has everything. History, calm lifestyle, excellent wines, charming explorable towns, nice seaside, not to mention the outstanding culinary scene. Truffle hunting is my favorite experience in Tuscany.”

Popular Tour Itineraries Featuring Tuscany

Spend some time in Tuscany on a tour that takes in other cities in Italy and neighboring countries. Our vacation packages including Tuscany 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.

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