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Navigate through the picturesque landscapes of Tuscany with the Tootbus Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.
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Tuscany 2-Days 5-Cities Flexible Sightseeing bus tour
2 days
Free Cancellation
4.5
(4)
from
$72
Discover Tuscany from a truly unique perspective with this small-group horseback riding experience through rolling vineyards and olive groves, followed by a traditional lunch and wine tasting at a local estate. Departing from Florence or San Gimignano, this experience offers the perfect balance of scenic adventure and authentic flavors, allowing you to explore the countryside away from the crowds and savor regional specialties paired with estate-produced wines. Ideal for nature lovers and food enthusiasts alike, it’s an unforgettable way to immerse yourself in the beauty, tastes, and traditions of Tuscany, all in one day.
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Tuscany Horseback Riding and Winery Tour with Lunch
7 hours
Free Cancellation
5.0
(23)
from
$126
Step into the Middle Ages on this 2-hour private tour of San Gimignano, one of Italy’s most stunning medieval villages. Stroll through historic squares, admire ancient towers, and choose to visit the majestic Cathedral or climb the Big Tower for breathtaking views. Discover local traditions, art, and flavors, including award-winning gelato and DOCG Vernaccia wine.
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Private Tour in San Gimignano
2 hours
Free Cancellation
4.9
(56)
from
$163
Price varies by group size
Navigate through the picturesque landscapes of Tuscany with the Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.
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Tuscany 5-Days 5 Cities Flexible Sightseeing bus tour
5 days
Free Cancellation
4.5
(5 Operators)
from
$89
Combine your San Gimignano sightseeing with a taste of the local terroir on this organic winery visit. Go behind-the-scenes at the family-run farm and vineyard, tour the facilities, and then indulge in a generous wine tasting. You’ll also sample locally made olive oils and balsamic vinegars, and enjoy a classic Tuscan feast of bruschetta, pasta, and more.
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Private Wine & Oil Tasting with Lunch
1 hour 30 minutes
Free Cancellation
4.6
(117)
from
$79
Visit two Tuscan wineries without having to worry about designating a driver by opting for this tour that includes transportation. Immerse yourself in the Chianti wine region as you sample a variety of wines. Discover the art of winemaking through tastings while enjoying the scenery of the Tuscan countryside. Then head to San Gimignano to spend some time exploring its medieval ramparts.
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Tuscany Wine Tour: 2 Wineries & Chianti from San Gimignano
6 hours
Free Cancellation
4.8
(72)
from
$94
Escape to the heart of Tuscany with a private vineyard experience in San Gimignano. Discover the secrets of biodynamic winemaking and olive oil production at a historic family-run farm. Enjoy a guided tasting of organic wines, extra virgin olive oils, and balsamic vinegar, paired with a delicious farm-to-table Tuscan meal.
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Private Tuscan meal with Wine and EVO oil tasting
1 hour 30 minutes
Free Cancellation
4.8
(46)
from
$79
Navigate through the picturesque landscapes of Tuscany with the Tootbus Tuscany Multi-Day Pass. Enjoy unlimited travel across Florence, Pisa, Siena, Lucca, and San Gimignano, allowing you to explore at your own pace. This flexible pass eliminates the stress of rigid schedules, offering scenic routes through the stunning Chianti countryside. With Tootie, your AI-powered guide, receive personalized recommendations and real-time travel tips in over 50 languages, making your journey seamless and enriching. Start your adventure from any city at any time and immerse yourself in the beauty and culture of Tuscany.
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Tuscany 3-Days 5-Cities Flexible Sightseeing bus tour
3 days
Free Cancellation
4.5
(5 Operators)
from
$81
Discover the authentic flavors of Tuscany on our Family-Friendly Tuscany Tour — a perfect mix of food, wine, and fun for all ages! Travel through the scenic Chianti countryside and visit a local farm overlooking San Gimignano, where you’ll taste local honey, cheeses, and fresh bruschetta with seasonal ingredients. Continue to a traditional winery for a light lunch with balsamic and olive oil tastings. Adults can enjoy a tasting of three Tuscan wines, while younger guests and non-drinkers are treated to grape juice or refreshing soft drinks. Finish the day with free time to explore the medieval streets of San Gimignano before returning to Florence. A delicious and family-friendly Tuscan experience that everyone will love!
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Family-Friendly Tuscany Day Tour for Wine Lovers and Non-Drinkers
7 hours
Free Cancellation
5.0
(11)
from
$167
Price varies by group size
Likely to Sell Out
Discover the magnificent architecture of the Renaissance on this full-day tour from Florence to Pisa and Lucca. Explore the famous marble monuments of Pisa’s Piazza dei Miracoli with a guide, including the city’s grand cathedral and vaulted cemetery. For the ultimate Pisa experience, climb the famous leaning tower and soak up panoramic views. After a stop at a local vintner’s shop for wine tasting, continue on to the medieval walled city of Lucca, where you’ll enjoy free time to stroll the well-preserved streets and squares your own.
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From San Gimignano: Pisa Half Day Trip
6 hours
Free Cancellation
4.2
(6)
from
$57
Soak up the local vino and small-town charm of San Gimignano on this wine tasting trip from Siena. Explore San Gimignano first at your leisure, spotting landmarks such as the Collegiata and Pizza del Duomo while strolling the medieval streets. Afterward, travel deeper into the Tuscan hills, and enjoy an intimate winery tour. Sip and swirl Chianti blends with an inside look at the winemaking process.
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San Gimignano Wine Tasting & Tuscan Dinner at a Local Winery
4 hours
Free Cancellation
4.5
(203)
from
$70
Likely to Sell Out
Tuscany is Italy’s gastronomic heart and this full-day tour from San Gimignano is the ideal introduction for traveling foodies. Sample regional wines and Tuscan specialties at a Montalcino winery; enjoy a self-guided tour of Montalcino fortress; taste regional delicacies such as Pecorino cheese in Pienza; and discover the famous Nobile di Montepulciano wine at a Montepulciano winery.
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Chianti & Montalcino Wine Tour from San Gimignano
8 hours
Free Cancellation
4.3
(6)
from
$163
Discover the essence of Tuscany on this immersive wine tour through the beautiful Chianti region. Visit three distinct wineries, where you'll explore traditional vineyards and enjoy multiple tastings of exquisite Chianti wines. With a knowledgeable guide leading the way, you’ll learn about the art of winemaking while soaking in the stunning countryside views. Perfect for adults seeking a delightful day of wine and camaraderie.
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Ultimate Tuscany Wine Tour: 3 Wineries & Tastings from Florence
6 to 7 hours
Free Cancellation
5.0
(5)
from
$188
Likely to Sell Out
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 delightful wine tasting at a nearby vineyard. Stroll around Monteriggioni, a medieval village where you can admire the ancient walls. At a beautiful wine estate, take part in a wine tasting savoring the rich aroma and ruby-red tones of Chianti wine crafted from Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes.
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Chianti and Castles Tour from San Gimignano Small Group
6 hours
Free Cancellation
5.0
(1)
from
$138
Likely to Sell Out
Visit two renowned wineries—and enjoy two separate tastings—during this full-day, small-group wine lovers’ tour of Tuscany’s Chianti region. Head to scenic, medieval-era Castellina In Chianti to enjoy Chiani wines paired with traditional cured meats. Then, head to Fattoria Lornano for a chance to sample even more local vintages along with extra virgin olive oil.
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Castles & Chianti Wine Experience– Small Group from San Gimignano
7 hours
Free Cancellation
4.1
(22)
from
$99
Discover the most beautiful places of San Gimignano and the surrounding Chianti area starting from Florence with our professional photographer and our guide who will take you wonderful photos in the village and on the hills among the vineyards. You will not be a passive spectator, but you will be the center of attention, free to enjoy the experience without hindrances such as cameras and various devices. Once the tour is over the photographic material will be shared telematically already edited.
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Private tour San Gimignano-Chianti w/ photographer from Florence
6 hours
Free Cancellation
5.0
(11 Operators)
from
$349
Price varies by group size
Make the most of your time while your ship is docked, and avoid the hassle of planning logistics, on this private tour of Siena and San Gimignano. Drive through the Tuscan countryside to bustling Siena, walk its winding streets with your guide, and visit the Duomo and the central square, famous for the annual horse race. Next, head to the charming UNESCO-listed town of San Gimignano and immerse yourself in its medieval surroundings.
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The best of Siena and San Gimignano from Livorno
8 to 9 hours
Free Cancellation
5.0
(3)
from
$989
Per group
In the heart of Tuscany and Chianti. Hills, vineyards, unspoiled nature. Intact medieval cities. Unforgettable atmospheres.
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San Gimignano and Abbey of San Galgano
6 to 7 hours
Free Cancellation
5.0
(33 Operators)
from
$640
Per group
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