Tuscany Shore Excursion: Chianti Wine Country and San Gimignano

A Chianti Wine Tasting Excursion

4.88 (151) ·
Travel Flexibly
· 9h · Florence, Italy

This private Livorno Shore Excursion takes care of all the details, from port pickup to drop-off, so you can relax and enjoy Tuscany’s treasures. Discover the medieval charm of San Gimignano, drive through the scenic Chianti Hills, and indulge in a farmhouse lunch with local delicacies and plenty of wine to taste. Experience the best of Tuscany’s food, wine, and breathtaking scenery, all stress-free and perfectly tailored to your day.

What You Get With This Tour

  • Port pick-up and drop-off
  • Luxury transportation
  • Free time in San Gimignano
  • Lunch at Chianti farmhouse
  • Olive-oil tasting
  • Winery tour
  • Wine tasting
  • Private tour
  • Guide gratuity
  • Wheelchair accessible

Tour Itinerary

  • 1

    Door-to-Door Transportation

    Your driver will pick you up from the port of Livorno in a climate controlled vehicle right from your ship. Begin your journey as you work your way to through the heart of Tuscany.
  • 2

    The Drive

    While driving from Livorno port to San Gimignano, enjoy views of the awe-inspiring Tuscan countryside.
  • 3

    More Vino

    It's time to visit the second vineyard on our itinerary where you'll taste a completely different type of Tuscan wine.
  • 4

    San Gimignano

    Known as the "Town of Fine Towers", San Gimignano is one of the most iconic places in all of Tuscany!
  • 5

    Medieval Skyline

    The city has managed to preserve 14 of it's towers, maintaining it's spectacular medieval skyline.
  • 6

    Organic Farmhouse and Tasting

    The first stop on our tour is a visit to an operational family farmhouse where you'll taste locally-grown products.
  • 7

    Meet the Locals

    It's important to meet the people who farm these incredible lands. Enter our friend Silvano who will greet you on arrival.
  • 8

    Organic Lunch

    Tuck into some delicious food. Staying true to the Italian Slow Food movement, enjoy an organic lunch full of Italian delicacies.
  • 9

    Happiness

    Need we say much more? Tuscan wine makes us all happy!
  • 10

    Winery Tasting

    Be warned, once you try the biodynamic/organic wines at this vineyard, you may never drink another type of wine again.
  • 11

    Sleep Well

    After a day like today, you'll undoubtedly have the best night's sleep ever.
  • 12

    Transportation Included

    Tuscany Shore Excursion: Chianti Wine Country and San Gimignano
  • 13

    Picturesque town

    Explore the streets of this lovely hill-top town and perhaps take the opportunity to indulge in a coffee or gelato while you stroll.

Additional Information

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 driver. 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.

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Customer Reviews

4.88 (151)
Leave a review
Eloise F., 22 January 2026

Amazing Full Day Trip During Our Cruise
Tanish B., 22 January 2026

This was a top cruise day trip! Our private driver made it easy to get from cruise port to the Tuscan gems. The San Gimignano towers were stunning, the farm to table lunch was delicious, and the wines was poured freely. All the details were covered perfectly. We definitely felt pampered and full by the end when we were brought back to our ship. Thank you Flavia and The Tour Guy!

Lovely Streets
Zachary P., 10 January 2026

Walking through the streets of San Gimignano was lovely. We saw famous places and also quiet areas. It felt real and not rushed like some tours can be.

Matheo D., 09 January 2026

Farm Wine Fiesta
Luisa B., 29 December 2025

From ship to Chianti farms with San Gimignano the stop everything was great.! Wandered the towers and shopped a bit. Lunch and tastings were mouthwatering. Relaxed return to port. Ideal for couples or families, highly recommend.

Show more reviews

Frequently Asked Questions

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.

Start From: $2,076.24

Available days Discounted days

Free cancellation up to 7 days in advance!