Tuscany Shore Excursion: Chianti Wine Country and San Gimignano
A Chianti Wine Tasting Excursion
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.
- 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
See what people are saying
4 total reviews
Leave a reviewLovely day!
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!
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!
Unverified Review
The wine was great, the tour was awesome and our guide was pleasant! Such a great way to spend the day!
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.
You may also like
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
Guided Tour
Florence Evening Food Tour with Florentine Steak and Tuscan Wine
Indulge in 14 authentic tastings across 5 local restaurants for the ultimate Florentine food journey
Skip the Line
Statue of David Evening Tour
Skip the line to see Michelangelo's David on a later tour of the Accademia Gallery with fewer crowds
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
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
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
Skip the Line Uffizi Gallery Tour
See Botticelli, Caravaggio, and Michelangelo's masterpieces in Florence's famous Uffizi Gallery
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
Skip the Line Duomo Terraces Tour with Dome Climb
Admire the Florence Cathedral, climb to the top of Brunelleschi’s Dome, and enjoy breathtaking views
New Tour
Tuscany in a Day Tour from Florence
Visit Siena, dine at a Chianti vineyard, explore San Gimignano, and see the Leaning Tower of Pisa!
Accademia's David and Uffizi Half-Day Skip the Line Tour
Explore Florence's must-see masterpieces including the Duomo in a small group
New Tour
Florence Duomo Skip-the-Line Tour
Explore the iconic cathedral with an expert guide and visit the fascinating Misericordia Museum
New tour
Pisa and The Leaning Tower Half Day Tour from Florence
Explore the City famous for its Piazza dei Miracoli and enjoy skip-the-line access with this tour
New Tour
Florence Accademia Gallery Express Guided Tour
Skip the line, marvel at renowned masterpieces and see Michelangelo’s iconic David statue!
New Tour
Chianti Vineyards Tour and Wine Tastings from Florence
See two luxurious wine estates, taste local wine, and sample delicious produce on this half day 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
Cinque Terre Tour with Locally Produced Limoncino Tasting from La Spezia
Explore the Beaches and Picturesque Peaks in a Small Group
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
Complete Florence Duomo Tour with Dome Climb and Secret Terraces
View this charming city from the hidden terraces of Brunelleschi’s dome after touring the cathedral
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
Cinque Terre Hiking Tour from La Spezia
Walk clifftop trails to discover vineyards, epic views, and famous villages on Italy's magical coast
New Tour
Pasta Cooking Class and Gourmet Wine Pairing in Florence
Create authentic pasta with a Michelin-star chef and savor Tuscan wines guided by a master sommelier
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
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
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
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
Tuscany Wineland Safari from Florence
Get off the beaten track across vineyards, castles and Chianti wine and chees on this 4x4 experience
Skip the Line
Kid-Friendly Private Florence Walking Tour: David & Gelato
Bring the fun to Florence on this family walking tour that includes a merry-go-round and papermaking
Private Tour
Private Wine Day in the Chianti Hills from Florence
Enjoy an intimate day trip tasting wine and organic food from local farms and vineyards in Tuscany
Private Tour
Private Pisa Day Trip from Florence with Lunch in Vinci
Discover Tuscany on this VIP private tour, with Leaning Tower of Pisa, Da Vinci Museum, and more!
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
Private Tour
Orvieto, Civita di Bagnoregio & Winery Private Day Trip from Rome
Escape the city on a memorable journey through Umbria’s historic towns to taste fine local wines
Private Tour
Livorno Shore Excursion: Florence & Pisa
Maximize your day ashore on this jam-packed private tour with Leaning Tower, David, and more!
Skip the Line
Private Siena Walking Tour
Explore this charming Tuscan city with an engaging local guide to see the Duomo, San Domenico & more
Brunello di Montalcino Helicopter Tour from Rome or Florence
Soar above Tuscany on an exclusive VIP tour, complete with private wine tastings and a gourmet lunch
Pisa & Cinque Terre Day Trip From Florence
Explore the charming towns of Monterosso and Manarola, embark on a coastal hike, and tour Pisa
New tour
Authentic 4-Course Meal at a Local’s Home in Florence
Watch your host’s cooking demo from her own kitchen, then enjoy a family lunch or dinner together!
New Tour
Tuscan Countryside Vespa Tour from Florence
Cruise to the rolling hills of Tuscany and taste local food and wine!
E-Bike Tour Through Florence and Tuscan Countryside
Ride along Tuscany’s majestic rolling hills, visit a medieval village, and sample local delicacies!
Chianti Vineyards 3-Course Dinner with Transportation from Florence
Escape to Tuscany for an evening of wine tastings, savoring 4 exquisite wines and local cuisine
New Tour
Tuscany Winery Tour and Gourmet Bites in Montalcino
Pair irresistible wine with delicious gourmet bites after strolling through picturesque vineyards
Val d’Orcia Day Trip with Two Wine Tastings from Florence
Sip on Brunello in Montalcino, wander through Pienza, and savor pecorino cheese in Montelpuciano
New Tour
Brunello di Montalcino Winery Tour & Tasting
Sip wine and stroll through vineyards alongside an expert guide in the hills of Montalcino
500 tour from Florence
Private Vintage FIAT 500 Chianti Tour with Driver from Florence
Cruise through the hills of Tuscany in style and dine at a Tuscan villa on this exclusive experience
Palazzo Vecchio Small Group Skip the Line Guided Tour
Roam through the lavish apartments and halls that were home to the iconic Medici family in Florence
Three-Day Chianti Vineyard Wine & Spa Getaway
Rejuvenate at the rustic Borgo Casa al Vento while learning the secrets of Tuscan wine and cuisine
New Tour
Early Morning Duomo Tour with Exclusive Entry and Brunelleschi's Dome
Be among the first of the day to enter Florence cathedral on this VIP experience
New Tour
San Lorenzo Market Tour and Wine Tasting in Florence
Eat your way through Florence’s historic market, enjoy a wine tasting, and try real Italian gelato!
New Tour
Pizza and Gelato Cooking Class in a Tuscany Farmhouse in Florence
Pick fresh ingredients and learn to make authentic, Italian cuisine on an unforgettable day trip!
Sant’Ambrogio Market Tour and Cooking Class with a Local Chef in Florence
Discover Tuscan street food, prepare a 3-course meal with tagliatelle and tiramisù and try 2 wines
New Tour
Oltrarno Local Food Tour in Florence
Take a break from the crowds and eat like a local in the lively neighborhood of Oltrarno
Florence Duomo Skip-the-Line Tour with Dome Climb
Explore the breathtaking cathedral and take in captivating views from Brunelleschi’s Cupola!
Vintage FIAT 500 Tour from Florence
Vintage FIAT 500 Self-Drive Tuscany Tour from Florence
Get behind the wheel of an iconic Italian car, cruising to the Tuscan countryside
New Tour
Tuscany Day Trip from Rome with Vineyard Lunch and Wine Tasting
Wander through the medieval towns of Montepulciano and Pienza and enjoy a 3-course meal!
