Chianti Authentic Experience with two Wine Tastings and two charming Villages | Get the Best Prices with Headout
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Half Day Tour of Chianti with Unique Tuscany Wine Tasting Experience

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6 hrs 30 mins
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Explore the medieval settlements nestled in the rolling hills of the Chianti region and sample authentic Chianti wine in the lovely family-run winery in the Sienese area. The entire area has a rustic vibe to it that captures the essence of medieval Europe and is an essential Italian experience not to be missed!


  • Journey to some of the most picturesque locations including vineyards, farm houses, castles and churches in the rolling hills of the Chianti region.
  • Sample two native wines.
  • Visit two of the most charming medieval villages in Tuscany - Greve and Castellina.
  • Travel along the alluring Via Chiantigiana.
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Why You Shouldn’t Miss This

Any mention of Chianti tends to conjure an image of exquisite wine perfectly packaged in an elegant fiasco (traditional straw basket). This region is a pastoral vision filled with structures that were built in the medieval era. Chianti wine has seen multiple mentions in popular movies such as The Silence of the Lambs. Some of the earliest references to Chianti wine date all the way back to the 13th Century. The political and military alliance, Lega del Chianti (or League of Chianti), formed in 1398, was intended to enhance the production and quality of wine in the area. To this day, Chianti wine has managed to maintain its unique flavour and is still one of the best in the world.

Greve is a small town that is situated many miles off the main highways that criss-cross throughout the country. Its considerable distance from Florence has allowed it to remain relatively free of traffic and over-industrialisation. It is a paradise nestled in the rolling hills of the Chianti region. It derives its name from the river that flows through it.

Situated in a lush river valley, Castellina is a picturesque comune in the province of Siena. The hamlet is famous for its Etruscan roots. The Rocca Castle, constructed in the 14th Century, is one of the main attractions here.

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Your Experience

A delightful winery in Chianti Classico is the first stop on the tour. A passionate winemaker will guide you through the wine cellars and briefly explain the winemaking process. This winery produces some of the best Chianti Extra Virgin Olive Oil. You will get an opportunity to sample some of these fine wines and other local products before heading to Greve.

Forests, villas, dreamy castles and romanesque churches dot the landscape. Walking through this naturally well-endowed region of Tuscany is a treat to the senses. When you finally reach Greve, you can spend some time in the main square of the ancient ‘market’. There are many tiny shops that sell fascinating merchandise that you can take home with you as souvenirs.

Travel along the Via Chiantigiana and marvel at the scenic landscape of the Chianti Classico region. Visit the family-run winery in the Sienese area. Stroll in the colourful garden and unwind in this beautiful winery. You can taste up to four different types of wine and other local products here.

From April to October, a short visit to Castellina is also included with this tour. It is a fortified hilltop village that was built during the Etruscan era. There are many quaint and charming houses and shops here that seem to draw you into the medieval feel of the town. Your guide will also take you to the local historical centre before your tour comes to an end.

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  • Transport in a top-notch van
  • Tour escort
  • Wine tastings with snacks
  • Assistance at the meeting point
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  • Stop at Castellina from November to March
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Know Before You Go


The tour begins at 1:15 PM and is available in all seasons on all days of the week. Please arrive 15 minutes before the scheduled departure. The tour lasts for 6 hours and 30 minutes.

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Strict Cancellation Policy

This experience cannot be cancelled, amended or rescheduled.

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My Tickets

You will receive an email confirmation along with your mobile voucher shortly. You can show your mobile or printed voucher along with some valid photo ID before the tour commences.

Meeting Point

Piazzale Montelungo - Caf Tours and Travel - Gray Line Yellow Street Sign.


This tour is valid for the date selected at the time of booking.

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