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Chianti Wine Region
Livorno Shore Excursions - Chianti Wine Region
 



Private Livorno wine tour through the Chianti wine region, visiting the medieval villages of Greve, Castellina, Radda, and Panzano in Chianti. Sample Tuscan wines at local enoteche, see an Etruscan tomb near Castellina, and visit Radda, seat of the medieval Chianti League from 1384. About 64 miles (103 km) from Livorno. Private English speaking driver guide, round trip.

9 hours (private)
private excursion
driver guide
english speaking local
all group sizes
sedan to full size coach
››
port or hotel
pick up either location
  • Pick up from Port of Livorno
  • Your contact will hold a welcome sign with your name written
  • Private English Speaking Driver Guide
  • Round Trip Transportation in Private Vehicle
Read Full Tour Description





Tour Number:
ILIVO-08


Group Size (Prices in USD)*:
2 People - $560 Per Person
3 People - $374 Per Person
4 People - $292 Per Person
5 People - $234 Per Person
6 People - $196 Per Person
7 People - $178 Per Person
8 People - $155 Per Person



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TOUR DESCRIPTION
 

Chianti Wine Region Shore Excursion from Livorno

This tour visits the Chianti Wine Region where you have the chance to explore small medieval villages and sample Tuscan wines as you travel. This area is considered the most picturesque in Tuscany.

Your driver guide will meet you at the pier in Livorno and you start your day driving through the rolling hills of Tuscany and into Italy's most famous wine-producing area, located about 64 miles (103 km) from Livorno. During your tour, you stop to visit wine producing villages, such as Greve in Chianti, Castellina in Chianti, Radda in Chianti or Panzano where you are encouraged to visit the local enoteca (wine shops) which offer wine tastings.

Between each village you drive through vineyards and pass hilltop castles. Many of these castles are wineries and some have wine rooms open to the public for tastings.

Castellina in Chianti has more of a medieval feel than others in the region. Its history dates back to the Etruscans when this was a major population center. The Via della Volte is a tunnel street that has windows overlooking the valley below. Just outside of town on the road to Radda is a perfect example of an Etruscan tomb, Ipogeo Etrusco di Montecalvario. It is a green hill surrounded by pine trees and topped by a pair of cypress trees. There is a stone walled tunnel that leads to the burial chambers.

Greve in Chianti is the unofficial capital of the Chianti Region. It came to prominence in the 13th and 14th centuries as a major trading center. The town square (which is more of a triangle) is filled with dozens of wine and gift shops and cafes. It is the host of the Chianti wine festival each September.

Radda in Chianti is a medieval hilltop town which is enclosed by large defensive walls. The town has existed since the 9th century and from 1384 was the seat of the Chianti League, the medieval alliance of Radda, Castellina, and Gaiole.

Panzano in Chianti is an attractive town located on a high ridge almost exactly halfway between Siena and Florence. Here you will see parts of its castle incorporated into the church and a nearby tower.

After a day of exploring the Chianti region, you return to the pier in Livorno.

If you cannot find what you are looking for, our Livorno tours and Livorno Shore Excursions can also be customized to fit your needs. If you have a larger group, we can offer you a private Livorno tour using a mid-size bus or full size coach. Please contact us with any questions or to receive a customized quote.

What's Included

Included

  • Pick up from Port of Livorno
  • Your contact will hold a welcome sign with your name written
  • Private English Speaking Driver Guide
  • Round Trip Transportation in Private Vehicle

Not Included

  • Meals and beverages not mentioned in the itinerary
  • Gratuities (optional, at your discretion)
  • Personal shopping

Tour Timing

All times are approximate and will vary based on your group's pace and interests.

  • 1
    2 Hours (traffic pending)
    Drive to Chianti Wine Region
  • 2
    4.5 Hours
    Explore Wine producing Towns
  • 3
    2 Hours (traffic pending)
    Return to pier in Livorno

Resources

Port of Livorno, Porto di Livorno 2000 Cruise Terminal. Official cruise terminal operator, departure point for this excursion. Official Website

Frequently Asked Questions

What is the story behind Chianti's Black Rooster symbol?
According to medieval legend, Florence and Siena agreed to settle their dispute over the Chianti territory by having a knight from each city ride out at the crow of a rooster, marking the border where they met. Siena chose a well fed white rooster, while Florence chose an underfed black rooster that crowed before dawn, giving its knight a head start and helping Florence claim most of the territory. The Lega del Chianti adopted the Black Rooster, or Gallo Nero, as its emblem in 1384, and it remains the symbol of Chianti Classico wine today.
Will we get to taste wine on this tour?
Yes. You stop in wine producing villages such as Greve, Castellina, Radda, and Panzano, where you are encouraged to visit the local enoteche, or wine shops, for tastings. Some castles and wineries along the route also have wine rooms open to the public. (Cost not included)
How much walking is involved in this tour?
This tour involves walking on uneven surfaces in hillside medieval villages, so comfortable, supportive shoes are recommended. Folding wheelchairs are welcome, though some areas may not be fully accessible; please let us know in advance so we can plan accordingly.

Also Available:

›Flexible Florence and Pisa - Tuscany and Florence shore excursion from Livorno cruise port - private guided visit to the Leaning Tower of Pisa and the Duomo (cathedral), a Romanesque masterpiece dating back to the 11th century with a licensed English-speaking driver guide.
›Extended Day - Florence and Pisa - Tuscany and Florence shore excursion from Livorno cruise port - private guided full day in Florence and Pisa, including the Leaning Tower, the Duomo, Giotto's bell tower, and the Accademia or Uffizi Gallery with a licensed English-speaking guide.
›Venice Highlights & Gondola ride - Venice shore excursion from Venice cruise port - private guided tour including a Grand Canal cruise, exterior visits to the Doge's Palace and St. Mark's Basilica, and a gondola ride through the canals with a licensed English-speaking guide.
›Ravenna Cruise Port to Venice Hotel Transfer (Water Taxi Included) - Private transfer from Ravenna Cruise Port to Venice Hotel — direct, door-to-door service with a professional English-speaking driver. No shared shuttles, no stops, no stress. Water taxi included.

Our Back-to-Ship Guarantee

Every excursion returning 1.5 hours before departure is covered. If we are late, we cover your costs to reach the next port. More info ›


Average Rating: Average Rating: 5 of 5 5 of 5 Total Reviews: 64 Write a review »

  3 of 3 people found this review helpful:
 
5 of 5 Review Location- Livorno Saturday, August 8, 2026
Reviewer: Walter H from Union Hall VA  
We had a wonderful vacation. Every one of the tour guides were great. My family was really impressed with their knowledge, service, and friendliness. I was pleasantly surprised with how much better an experience we had compared to the Princess Cruise Ship Tours. For example, our tour guide for the Amalfi Coast and Pompeii knew that Pompeii was closed until 1130 AM and changed our itinerary to travel along the coast in the morning and go to Pompeii at the end of the day. The other tours just took people to the gate and waited for two hours. Thanks again. My wife and kids felt that each guide was a   friend   by the end of the tour. The guides in Florence and Ephesus were probably the highlight for us. The Mercedes vans that were used in most cities were always nice and all of our drivers were really great. Ive already recommended you to a friend.

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  0 of 0 people found this review helpful:
 
5 of 5 Review Location- Livorno Sunday, August 2, 2026
Reviewer: Awilda L from Coral Gables FL  
We had a great time. Max did A great job. We really enjoyed it. Stefano was our driver a great help. Thank you.  We tipped him well.  Hope he remembers us!

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  0 of 0 people found this review helpful:
 
5 of 5 Review Location- Livorno Sunday, August 2, 2026
Reviewer: Pamela E  
I have just returned from our Mediterranean Cruise and want to thank you for the wonderful private tours you assisted us with. I have already given your website to two prospective clients who inquired about our tours in Spain, Italy and Greece. Thank you once again we will be using your assistance in the future.

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  0 of 0 people found this review helpful:
 
5 of 5 Review Location- Livorno Sunday, July 26, 2026
Reviewer: Anna A from Nicosia, Cyprus  
Indeed the private shore trip to Pisa and Florence was fantastic. Our driver, Max was very friendly and helpful.

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  0 of 0 people found this review helpful:
 
5 of 5 Review Location- Livorno Thursday, July 23, 2026
Reviewer: Ken Z from Calgary AB  
Today was our last excursion booked through your company. The trips in Florence and Nice were both great, with good hosts. But by far the best guide was Tom today in Kotor. He is excellent and I cannot say enough good about his knowledge and demeanor. 5 stars for him.Thanks for all

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