Tuscany Shore Excursion: Chianti Wine Country and San Gimignano

A Chianti Wine Tasting Excursion

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.


While you will spend some time in the car, once you are in San Gimignano and the wine country, you will be walking the rest of the time.

9 h
custom size
from 2 reviews
1 Door-to-Door Transportation
2 The Drive
3 San Gimignano
4 Medieval Skyline
5 Picturesque town
6 Organic Farmhouse and Tasting
7 Meet the Locals
8 Organic Lunch
9 More Vino
10 Winery Tasting
11 Happiness
12 Sleep Well


Food & Wine
Tuscan Countryside
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. 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.