Wine and cheese · Tuscany
Prices checked 2026-11-04.
GetYourGuide, Viator and Musement list 82 wine tours and tastings that name San Gimignano. Prices run from €39 to €1,143 a person, €265 in the middle of the range. 15 are rated 4.5 or better from at least ten reviews; those come first below.
Every listing on this page names San Gimignano in its title: tastings at its estates, tours that stop there, and lunches among its vineyards. For the rest of Tuscany, see the region's own lists below.
Best reviewed
4.8 (666)7 hours
Join a wine tour of the Tuscan countryside from Florence, tasting up to 7 wines at 2 wineries. Explore the beautiful Chianti landscape and visit one of the most famous Tuscan towns of San...
4.9 (521)9 hours
Discover Tuscany's charming towns on a guided tour with a small group of up to 25 people. Explore Siena, taste Tuscan wine, indulge in local cuisine, and wander San Gimignano's streets.
4.6 (207)9 hours
Discover the beauty of Tuscany on a full-day group tour to Siena and San Gimignano. Enjoy round-trip transport, expert guidance, and free time in both towns to explore at your own pace.
4.9 (112)8 hours
Enjoy 100% organic food, olive oil and wine tastings in Tuscany's Chianti region. Visit two wineries, have a delicious lunch, explore San Gimignano and see Florence from above.
4.7 (107)6.5 hours
Get a taste of Chianti; visit one of the world’s most enchanting areas with rolling hills, stunning scenery, quaint villages and vineyards. This comfortable minivan tour includes a stop i...
4.7 (72)12 hours
Enjoy a full-day tour through Tuscany’s rolling hills: visit Pisa’s wonders, taste Chianti wine with lunch, explore Siena’s history, and admire San Gimignano’s towers, all in one unforget...
4.8 (60)9.5 hours
Discover the villages of San Gimignano and Volterra by traveling through the Tuscan hills with a guide in a small group. Enjoy a day immersed in nature, food, and wine.
5.0 (47)8 h
Explore the beautiful Tuscan countryside with a private driver and customize your itinerary to visit Pisa, San Gimignano, Chianti and Piazzale Michelangelo. History, art, culture and brea...
5.0 (33)7 h
Explore the beautiful Tuscan countryside with a private driver and customize your itinerary to visit two wineries in Chianti and San Gimignano, with a 15-minute stop at Piazzale Michelang...
5.0 (29)8 h
Private tour to San Gimignano and Chianti with an English speaking driver in a deluxe minivan. Your driver will delight you with live commentary on board about Tuscany, general informatio...
4.9 (20)7 hours
Ride among vineyards, olive groves, and rolling hills with no experience. Visit Chianti's most attractive medieval village, taste world-champion gelato, and tour a winery with lunch and w...
5.0 (17)7 h
Experience the beauty of Tuscany on a private tuk-tuk tour through the Chianti countryside! Depart from Florence by shared bus/van, then enjoy an exclusive ride past rolling vineyards, st...
5.0 (15)7 h
This experience is 100% private and designed exclusively for you and your group. From private transportation to a dedicated local tour leader, every detail is tailored to your pace and in...
5.0 (12)5 h
This is a great opportunity to spend HALF DAY (5 hours) in Tuscany enjoying a great lunch and wine tastings. We will pick you up directly by your accommodation in Florence and we will he...
5.0 (11)7 hours
Only one day in Tuscany? Don’t mess it up. Skip crowded buses, max 8 by van with hotel pickup. Make cheese in San Gimignano and enjoy Chianti wine tasting. The one choice you won’t regret...
4.1 (57)12 hours
Would you like to see the most beautiful places in Tuscany on a memorable day? Join this tour for a magical experience, made even more enjoyable by a typical lunch and a tasting of local ...
4.1 (33)8 hours
Discover the stunning towns of Siena, San Gimignano, and Monteriggioni on a small group tour by comfortable minivan, exploring symbols of Medieval and Gothic architecture.
4.3 (25)11 hours
Start your journey in San Gimignano, a world-famous medieval hilltop town known for its ancient towers, frescoes and perfectly preserved historic centre. Your tour leader will escort you ...
5.0 (9)8 h
Spend a day through the Chianti sweet hills. A wonderful Experience between art, wine and local food to discover vineyards, towers and typical farms. • Meet your driver escort at your Cr...
5.0 (8)7 h
The best unforgetable tour in Tuscany in order to discover the real life in Tuscany. You will visit the great countryside, you will discover the old wineries so you can understand the o...
5.0 (8)8 h
* Private, Exclusive, Customizable, door-to-door tour of San Gimignano and Chianti Classico, wine and food Tour from Florence * 8 hours in a luxury Mercedes sedan/minivan with air condit...
5.0 (7)8 h
Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous fo...
5.0 (7)8 hours
Experience the magical Tuscan countryside, and visit two UNESCO World Heritage sites, on this private, customizable day trip, directly from your door.
5.0 (7)7 hours
Discover the Tuscan countryside on a sunset tour from Florence. Visit a winery for a tasting, explore San Gimignano, and enjoy a traditional Tuscan dinner paired with local wines.
5.0 (7)8 h
Admire the two gems nestled in the Tuscan countryside, Volterra and San Gimignano, the best medieval villages. A jump in the past, great atmospere in the Etruscan city. Visit the winery (...
5.0 (6)9.5 h
Discover 3 of the most authentic towns nestled in the heart of the tuscany countryside. Siena, the famous Palio city, San Gimignano, UNESCO heritage and Monteriggioni, one of the most en...
5.0 (6)9 hours
Experience the heart of Tuscany, from Florence to Siena, through Monteriggioni, Chianti vineyards, and the medieval charm of San Gimignano. Art, history, wine, and timeless landscapes.
5.0 (6)8 h
• ESPERIENZA PER IL TUO GRUPPO PRIVATO • This GUIDED tour will take you in the morning to visit the city of Siena accompanied by an expert official guide. The afternoon will be dedicated ...
5.0 (6)6 h
Medieval towers but also the best ice cream of the world! If your dream is to discover all the hidden corners of a Tuscan city, this is your tour. I will pick you up with my professional...
5.0 (6)8 h
The tour starts everyday from Florence (from Siena only on request) at around 9.30 and ends at around 4.30 pm Vernaccia di San Gimignano Wine tasting and Tuscan lunch with saffron (depen...
5.0 (6)8 h
Our exclusive food and wine tour begins in Siena, one of the most fascinating cities in Tuscany. The day begins with a visit to the majestic Siena Cathedral, known for its splendid Gothic...
4.2 (6)11 hours
Enjoy a full-day exploration of Tuscany's villages and wine regions, starting from Siena. Discover the beauty of San Gimignano, the Chianti wine area, and the Montalcino fortress.The day ...
4.0 (6)11h 30m
If you want to feast your eyes and tantalize your taste buds with the delights of Tuscany in one day, this tour is for you!Your day will begin with a free tour of Pisa. Here you'll have t...
5.0 (5)5 h
Tuscany...what else? Immerse yourself in the beauty of the Tuscan countryside and leave the confusion of the city. Spend half a day in the most famous wine region in the world (Chianti),...
5.0 (4)7 h
Spend a day visiting Volterra with its splendid Roman Theater and the "Beautiful Towers" of San Gimignano. A trip from the Etruscan period to the Renaissance. A wonderful experience among...
5.0 (4)9 h
Indulge yourself with a pleasant trip to the medieval cities of San Gimignano and Volterra. Admire the Tuscan countryside and take lovely pictures of the gently rolling hills as you snake...
5.0 (4)9 h
This tour includes a car at your disposal during the tour and a transfer to San Gimignano, where you’ll have free time to explore the beautiful medieval village of San Gimignano. Then tr...
5.0 (4)7 h
If you wish to get to know more about Tuscany, visit a beautiful medieval town and get to taste the wine and the local dishes in a relaxing athmoephere, this is the perfect tour for you.
4.8 (4)10 hours
On this private Tuscany day tour from Florence to Hills of Siena you will taste Tuscany. Your itinerary involves limited driving time so that you can thoroughly enjoy the places visited o...
5.0 (3)8 h
Indulge in the perfect tour for those seeking to explore the Tuscan Countryside. Your private driver, at your disposal for the day, will guide you through the picturesque Tuscan hills ado...
5.0 (3)8 h
This tour is designed for those who want to immerse themselves in the history, culture and flavors of one of the most fascinating regions of Italy. Stroll through the cobbled streets of t...
5.0 (3)6 h
Daily bike tour to discover San Gimignano, small walled medieval hill top town. San Gimignano has 13 unique and perfectly preserved tower houses which create a stunning hilltop skyline. F...
5.0 (3)8 h
Enjoy this private tour immersed in Tuscan countryside nature, culture and local wine and food. You will adore amazing views on the way to San Gimignano - a journey into the charm of the ...
5.0 (3)6 h
This small-group experience blends the iconic towers of San Gimignano with a personally hosted winery lunch at a family-run Chianti estate. Rather than rushing between multiple stops, the...
5.0 (3)5 h
Discover the charm of San Gimignano and experience Tuscany's culinary delights on this half-day tour from Florence. Begin your adventure in an air-conditioned van, taking in the picturesq...
5.0 (3)8 h
The beauty of the landscape all around and the experience of the tipical lunch in a local winery will be unforgettable
5.0 (3)10h 30m
Enjoy the coach ride from Florence to Monteriggioni, one of the medieval gems located on a hilltop among the beautiful Chianti hills. Inside its still intact walls, you will drink in hist...
5.0 (3)1.5 h
This tour is not a simple wine tasting, but you will have the opportunity to be accompanied by the producer in the vineyards and in the cellar, to get to know the viticulture and winemaki...
5.0 (3)9 h
Enjoy this unforgettable High Level Tour and make memories of the landmarks. A day exploring the landscapes and artistic small towns that Tuscany can offer: • San Gimignano • Monteriggio...
5.0 (3)6 h
Our driver guide will collect you at your accommodation, ( No meeting points, we pick you up at your place! ) setting off toward the heart of Chianti Classico. Experiences 1 day exciting ...
5.0 (3)1 h
Podere La Quercia offers an intimate and personal experience hosted directly by the producer. With limited capacity and reserved tables for each booking, guests enjoy a relaxed atmosphere...
5.0 (2)8 h
If you like cycling and admiring beautiful landscapes we will take you from the most famous wine area in Tuscany to the fantastic hilltop town known as the “Manhattan of the middle ages”....
5.0 (2)5.7 h
Leave the crowds of Florence behind and discover the beauty of Tuscany on this Chianti morning wine tour. Travel through the iconic Tuscan countryside and visit two charming wineries in t...
5.0 (2)4 h
TOUR HIGHLIGHTS • Taste some of the library reserve vintage wines including other wine from the current release vintage • Eat the Fiorentina Steak paired with the best wines directly from...
5.0 (2)8 h
A full-day tour to Siena and to San Gimignano, the medieval town considered a Unesco World Heritage Site. Lunch will be held at the Castle of Monteriggioni in a small medieval village cro...
5.0 (2)4.5 h
TOUR HIGHLIGHTS • Explore San Gimignano, vineyards and olive groves on a horseback ride • Take in the fascinating and warm landscape of the San Gimignano while enjoying a Tuscan tradition...
5.0 (2)8 h
A full day trip in the landscape of the rolling Chianti hills with a private tour, surrounded by cypress avenues, medieval villages. sunflower fields, tasting the best wines of our region...
5.0 (2)7 h
Spend a day visiting Volterra with its splendid Roman Theater and the "Beautiful Towers" of San Gimignano. A trip from the Etruscan period to the Renaissance. A wonderful experience among...
5.0 (2)8 h
Spend a day visiting Volterra with its splendid Roman Theater and the "Beautiful Towers" of San Gimignano. A trip from the Etruscan period to the Renaissance. A wonderful experience among...
5.0 (2)7 h
Our first stop will be in Siena which with its medieval monuments and art treasures is considered a world heritage site by UNESCO. We'll start our walk from the Basilica of San Domenico, ...
5.0 (2)2 h
A relaxed Tuscan light lunch just steps from San Gimignano’s historic center. A moment to slow down, sit, and enjoy a balanced combination of wine and traditional flavors in an authentic ...
5.0 (2)2 h
A few steps from San Gimignano do not miss a special food and wine experience: a tasting of the best Chianti wines with lunch included and grappa tasting!
5.0 (2)8 h
DA Florence and discover Siena, San Gimignano and the Tuscan hills. In Siena you will visit Piazza del Campo and the Duomo. In San Gimignano you can walk among the towers and enjoy a famo...
5.0 (2)5 h
Visit one of the most famous Italian wine areas, San Gimignano, with your private group followed by a wine tasting at a family-owned winery in the hills of San Donato in Poggio. Enjoy hot...
5.0 (2)2 h
Set in a stunning Tuscan vineyard, this winery tour and tasting offers a perfect mix of authentic flavors, culture, and family-friendly fun. Begin with a guided tour of the winery, where...
5.0 (2)6 h
Don’t miss the chance to visit the Chianti wine region and its rolling hills ! Spend half a day in the iconic landscape of the "Chianti Hills", among cypress avenues, vineyards, sunflower...
5.0 (1)8 h
A full day trip with an exclusive and private tour in the landscape of the rolling hills of Chianti, surrounded by avenues of cypress trees, medieval villages, ancient castles, sunflower ...
5.0 (1)5 h
Tuscany... What Else? Discover the Magic of Chianti & San Gimignano! Leave the chaos of the city behind and immerse yourself in the timeless charm of the Tuscan countryside. Spend half a...
5.0 (1)6 h
Enjoy a half-day journey from San Gimignano to the picturesque wine region of Chianti. Begin your adventure with a visit to the charming village of Castellina in Chianti, followed by a de...
5.0 (1)8 h
A scenic ride along the Via Francigena to San Gimignano: the home of Vernaccia wine and world-renowned gelato. With our E-bikes you’ll make your way to San Gimignano (a UNESCO world herit...
5.0 (1)9 h
When your boat docks at the Livorno Port, don’t waste time at the port. Book a private Tuscany day trip in advance, and head out with a guide, who’s serving also as your dedicated driver ...
5.0 (1)9 h
A customized day trip of Chianti countryside and San Gimignano for the discerning traveler seeking an authentic Italian experience on a small group tour for up to 7 people with only the v...
5.0 (1)8 h
Spend a full day in the iconic landscape of the Chianti hills, among cypress avenues, vineyards, sunflowers and medieval villages. Visit Siena and the historic village of San Gimignano, f...
5.0 (1)6 h
A wonderful day visiting the medioeval village of San Gimignano one of the main villages of Tuscany called the medioeval Manhatten because for all his towers and after 2 hours free to wal...
5.0 (1)8 h
Embark on a condensed yet captivating exploration of Siena and San Gimignano. Begin in Siena's heart at Piazza del Campo, marvel at the cathedral, and admire historic landmarks like Palaz...
5.0 (1)2.5 h
Experience a delightful Tuscan winery tour that combines a multi-course meal with a wine tasting. Start with a traditional appetizer platter featuring fettunta, homemade vegetable spread...
5.0 (1)9 hours
Your day starts in central Florence, where you’ll meet your small group of no more than 14 people and an expert tour leader. Then you’ll hop into private transportation and be spirited ou...
6h 30m
Spend the day in the stunning Chianti region, a region that mixes hilltop towns with top-notch wine tastings. Explore the UNESCO-listed San Gimignano and be in awe of the gently undulatin...
Are you in Florence and you want to visit Pisa, San Gimignano, Siena and Chianti on your own? To do this we offer our transport service with minivan and expert driver in English or Italia...
8 hours
You'll discover two of Tuscany's most iconic destinations on this full-day experience departing from Siena. Travel in comfort aboard an air-conditioned coach with an expert multilingual t...
Discover three of the most famous and fascinating towns in Tuscany: Siena, San Gimignano and Pisa. This full-day tour offers you the highest level of comfort as you will travel with a sma...
Three hundred years ago, aristocratic and noble young men from Europe began taking a trek through Italy in search of art, culture and the roots of Western civilization: the Grand Tour. Si...
Listings, prices and ratings come from GetYourGuide, Viator, Musement. We earn a commission when you book through these links; it does not change the price you pay.
At the table
The food and wine pairings our editors chose for Tuscany, the dishes you are most likely to meet on a tasting or at lunch.
Before you book
Across the 82 wine tours and tastings listed here, prices start at €39 and the middle of the range is €265 per person; 6 cost under €50. Prices are the marketplaces' own and were last checked on the date shown at the top of the page.
By rating and number of reviews on the marketplaces: From Florence: Tuscany Wine Tour, 2 Wineries & San Gimignano (4.8 from 666 reviews), Small Group Tour - Siena, San Gimignano & Chianti with lunch (4.9 from 521 reviews) and From Florence: Siena & San Gimignano Tour with Chianti Views (4.6 from 207 reviews).
Most take about a full day; the listing for each one gives its exact length.
Keep exploring
Hungry for more? Florence food guide on TableJourney, our sister site.
