Tuscany Shore Excursion: Chianti Wine Country and San Gimignano

A Chianti Wine Tasting Excursion

4.95 (94) ·

Travel Flexibly

· 9.00h · Florence, Italy

Tuscany Shore Excursion: Chianti Wine Country and San Gimignano

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

94 total reviews

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4.9/5 (based on 94 reviews)

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1 stars

01 November 2025

Reviewed by
Aliyah Jain

Comfort All Day

01 November 2025

Reviewed by
Aliyah Sinha

Luxury transport made the tour super comfortable. Our driver took care of every detail. We just enjoyed the ride and the beautiful scenery.

Tasty Olive Oil

17 October 2025

Reviewed by
Aarav Wood

Tried the best olive oil I’ve ever had in my life! Learned how it’s made and enjoyed dipping fresh bread. A tasty and fun moment.

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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.