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The quintessential Tuscan hilltop town

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.

"We will continue to recommend JayWay to our friends! This was our second time using JayWay to plan our Eastern European trips, and we could not have been more happy or satisfied!!! Thank you JayWay!"

Becca & Shawn

Becca & Shawn


"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

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.

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.

Italy Tours

Italian Dream Honeymoon

This ten day Italian honeymoon itinerary packs in Rome, Tuscany, Florence and Venice. Explore the Eternal City hand in hand. Relax poolside at a Tuscan farmhouse or palazzo. See the best of Florence in a day then spend the last three days in one of the most romantic cities in the world, Venice. read full itinerary

Italian Highlights in 11 Days: Rome, Tuscany, Cinque Terre & Venice

See Rome, Tuscany, Cinque Terre & Venice in a week and a half if traveling at a fast pace or take it slow and use this as a base for a longer tour and add some days. read full itinerary

Magical Italy: Rome, Amalfi, Tuscany, Florence, Venice in 2 weeks

Two weeks exploring some of Italy's highest highlights, starting in Rome, then the Amalfi Coast, followed by Tuscany, then Florence, finishing up in Venice. Truly magical! read full itinerary

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