Tuscany Shore Excursion: Chianti Wine Country and San Gimignano

A Chianti Wine Tasting Excursion

Travel Flexibly 5 / 5 See All 4 Reviews · 9.00h custom · Florence, Italy

On this Livorno Shore Excursion, visit charming San Gimignano and drive through the Chianti Hills to experience the best wine, food and scenery that this celebrated region has to offer. Includes lunch at a farmhouse and plenty of wine to taste.

  • Door-to-Door Transportation
  • More Vino
  • The Drive
  • San Gimignano
  • Medieval Skyline
  • Organic Farmhouse and Tasting
  • Meet the Locals
  • Organic Lunch
  • Happiness
  • Winery Tasting
  • Sleep Well
  • Transportation Included
  • Picturesque town

On this Livorno Shore Excursion, visit charming San Gimignano and drive through the Chianti Hills to experience the best wine, food and scenery that the region has to offer. The most famous of all wine regions, see for yourself why the Chianti region has been a favorite among artists and poets over the centuries. Sample the best that this amazing land has to offer.

Tuscany Chianti Shore Excursion Description

This full-day tour includes:

  • Private luxury transportation with climate-control

  • A visit to San Gimignano

  • Lunch and wine at an organic farmhouse

  • Wine tasting at a vineyard

Please note: If you’re not docking in Livorno, please reach out to our Travel Experts for alternative day trip options. We’d still love to provide you with an unforgettable experience in Tuscany.

Private Luxury Transportation from Livorno

To make this private shore excursion in Tuscany even better, we pick you up from the Livorno cruise port in a luxury climate-controlled vehicle. From there, on the way to San Gimignano, travel through the beautiful Tuscan countryside with your own personal guide. Travel past vineyards and olive groves, as you take in the gorgeous landscape of one of the most prestigious winemaking regions in the world.

San Gimignano

The first stop on this Tuscany shore excursion is an incredible place known as “Medieval Manhattan”. Situated on a hill, San Gimignano is a 10th-century town famous for its tall medieval towers. The surviving towers rise above the small houses and resemble skyscrapers from a distance. The main gate to the walled city dates back to the 13th century - since 1990 the historic city center has been on the UNESCO World Heritage list. Enjoy some time to wander around, shop, relax on the church steps or sit down for a local breakfast (food in San Gimignano is not included in the price of the Shore Excursion).

Chianti Farmhouse

Your next stop is an organic farmhouse in the heart of Chianti. Tour the farm and meet the owner, before sampling some extra-virgin oil, Chianti wine and truffle oil. Taste locally-grown products from the family's farm for a typical lunch of antipasto, primo, contorno more wine and a sweet snack to finish. Staying true to the Italian slow food movement, these Italian delicacies are sure to please your stomach. 

Visit a Vineyard for More Wine Tasting

The adventure continues to another winery for a tour of the vineyard and a chance to learn more about the rich art of winemaking. Tour the vineyard and learn more about the rich art of winemaking. Afterward, sample the estate’s biodynamic/organic wines for a true taste of the Tuscan countryside. The wine tasting is included. After the second vineyard, enjoy the comfortable drive back to Livorno. After all that beauty and wine, you’ll be happy to get back to your boat and get some rest.

What you get with this tour
Home-cooked Lunch at an Organic Farmhouse
Full Wine Tasting Experiences in Chianti
Our door-to-door service means that you get to sit back and relax.
Private luxury climate-controlled transportation
Tripadvisor Logo

See what people are saying

4 total reviews

Leave a review
5.0/5 (based on 4 reviews)
5 stars
4 stars
3 stars
2 stars
1 stars
Lovely day!
24 September 2019
U
Reviewed by
Unverified Review

I was on a cruise with my friends and we DESPERATELY wanted to do a wine trip in Tuscany. Because the port was a bit further away from that region, we didn't think we'd be able to do it. But then we came across this tour and we were THRILLED! We had roundtrip transportation from the port and then a fantastic day filled with amazing food, delicious wine, and unforgettable memories. Thanks Roman Guy for making this happen for us!

Great tour from a great company!
21 June 2019
U
Reviewed by
Unverified Review

This was a great shore excursion! Perfect if you're looking for a way to spend your time in Tuscany. Great wine, great guide, very simple, and amazing customer service.

Great Vineyard!
11 March 2019
U
Reviewed by
Unverified Review

The wine was great, the tour was awesome and our guide was pleasant! Such a great way to spend the day!

show more reviews

Frequently Asked Questions

Where to meet?

At the port of Livorno

What to bring?

Since you will be walking around for much the day so wear comfortable shoes and bring sunscreen in the summer.

What if I don't see availability on the day I want to go?

Just reach out to us and we will try our best to accommodate your scheduling needs.

Is the cost of lunch and wine included in the price?

While a wine tasting and lunch is included in the tour price, we do not provide additional food and drink in San Gimignano.

What if my ship isn't docking in Livorno?

If you aren't docking in Livorno, just reach out to us via email or toll-free number. We'd still like to provide you with an unforgettable experience in Tuscany.

How many people can I bring?

If there are more than seven people in your group, please contact us prior to booking so we can sort out the details.

How do we arrange the timing of this shore excursion?

Please reach out to us upon booking to provide the exact time you'll disembark from your ship and we'll take care of the details.

What to bring?

Since you will be walking around for much the day so wear comfortable shoes and bring sunscreen in the summer.

Where to meet?

At the port of Livorno

$91.51 per adult
+ $1,049.62 base price
Total: $1,141.13

available days discounted days

Reserve Now $91.51 / per person
$91.51 / per person
You may also like
Skip the Line
Up to 15 % off

Skip the Line

Florence in a Day Combo Tour with David and Uffizi

Explore Accademia Gallery, Ponte Vecchio, Florence Duomo, Uffizi Gallery, and so much more

Skip the Line
Up to 10 % off

Skip the Line

Florence Walking Tour with Statue of David

Uncover the best of Florence at the Duomo and Ponte Vecchio, and skip the line at Accademia

Day Trip
Up to 15 % off

Day Trip

Tuscany Wine Tour from Florence to Siena & Chianti

Enjoy a luxury Tuscany day trip to visit Siena and San Gimignano then taste food and wine in Chianti

Skip the Line
Up to 10 % off

Skip the Line

Skip the Line Uffizi Gallery Tour

See Botticelli, Caravaggio, and Michelangelo's masterpieces in Florence's famous Uffizi Gallery

Guided Tour
Up to 15 % off

Guided Tour

Florence Local Food Tour in Santo Spirito

Get an authentic taste of Florence’s exquisite food and wine in a lively local neighborhood

Skip the Line

Skip the Line

Florence Private Walking Tour with Michelangelo's David

Explore the famous sites of Florence, with Ponte Vecchio, Duomo, and skip-the-line Accademia entry

Skip the Line
Up to 15 % off

Skip the Line

Statue of David Evening Tour

See Michelangelo's David and tour the Accademia after hours without the crowds

New Tour

New Tour

Pizza and Gelato Making Cooking Class in Florence

Create the authentic food of Italy with an expert pizzaiolo chef, homemade lunch, and wine

Skip the Line

Skip the Line

Private Siena Walking Tour

See Siena Through a Local's Eyes

New Tour

New Tour

Authentic Tuscan Cooking Class in Florence with San Lorenzo Market

Create delicious pasta, tiramisu, and more with market-fresh ingredients and an expert local chef

Skip the Line

Skip the Line

Uffizi Private Tour in Florence

Skip the line to see Birth of Venus, Medusa, Doni Tondo, and more with your own private art guide

New Tour

New Tour

Tuscany Wine Making Experience and Gourmet Dinner from Florence

Dine like Tuscan royalty and create your own Chianti wine blend on this small group VIP evening tour

New Tour

New Tour

Semi-Private Cinque Terre Day Trip & Vineyard Tour from Florence

Discover the best of Cinque Terre with seafood lunch, wine tasting, and transportation included

New Tour

New Tour

Pisa and Lucca Day Trip from Florence

Book a stress-free trip to see the Leaning Tower of Pisa and Lucca's medieval walls in a day

New Tour

New Tour

Cinque Terre Day Trip from Florence with Boat Ride

Visit these iconic fishing villages the easy way on this tour to the beautiful Italian Riviera

New Tour

New Tour

Tuscany Wine Tour by Vespa from Florence

Taste the food and wine of Chianti as you ride through the Tuscan countryside on a vintage scooter

New Tour

New Tour

Skip the Line Florence Duomo Tour and Dome Climb with Secret Terraces

Climb Brunelleschi's famous dome for unforgettable views of Florence from the secret terraces

New Tour

New Tour

Florentine Gondola Boat Tour

Sip wine on the Arno River and cruise by Ponte Vecchio, Uffizi, and more on a classic Barchetto boat

New Tour

New Tour

Florence in a Half Day by Bike Tour

Take a ride through the city's hidden gems from Ponte Vecchio to the Oltrarno neighborhood

New Tour

New Tour

Tuscany Wineland Safari from Florence

Get off the beaten track to explore vineyards, castles, food, and Chianti wine on this 4x4 day tour

Skip the Line

Skip the Line

Kid-Friendly Florence Walking Tour: David & Gelato

Bring the fun to Florence on this private family walking tour, with merry-go-round and paper-making

Private Tour

Private Tour

Wine day in the Chianti Hills from Florence

Enjoy a private day trip tasting wine and organic food from local farms and vineyards in Tuscany

Private Tour

Private Tour

Pisa Day Trip with Lunch in Vinci from Florence

Discover Tuscany on this VIP private tour, with Leaning Tower of Pisa, Da Vinci Museum, and more!

Private Tour

Private Tour

Orvieto, Civita di Bagnoregio and Wine Tasting Day Trip from Rome

Visit the "Dying City" of Civita, Medieval Orvieto and a Delicious Wine Tasting at a Local Vineyard

Private Tour

Private Tour

Livorno Shore Excursion: Florence & Pisa

Maximize your day ashore on this jam-packed private tour with Leaning Tower, David, and more!

Private Tour

Private Tour

Brunello di Montalcino Helicopter Tour from Rome or Florence

Take to the skies on the ultimate VIP Tuscany tour that includes wine tasting and a gourmet lunch

Skip the Line

Skip the Line

Full Day Florence Dome Climb, David and Walking Tour

Tour the David Statue & Climb the Duomo With No Line

Skip the Line

Skip the Line

Ultimate Full Day Florence Tour with Dome Climb, David, and Uffizi Gallery

After Duomo Climb, see The David & Uffizi Art