San Gimignano Tours in October 2025
Planning for a trip to San Gimignano during October? We offer 10+ tour packages to San Gimignano departing in October 2025 that have 150+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of San Gimignano on your October holiday.
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10 Best October 2025 Tours in San Gimignano
Join one of these handpicked San Gimignano October 2025 tour packages, tailored to the season.
3% Off Today
Imagine wandering through the rolling vineyards and sun-drenched hills of Tuscany, glass of Chianti in hand, with Renaissance cities as your backdrop. The "Tuscany Walks & Chianti Wines" trip is tailored for seasoned travelers who appreciate a balance of invigorating exploration and cultural depth. Over eight days, this guided trekking tour lets you absorb the essence of the region at a comfortable, moderate pace, taking in Chianti, Siena, San Gimignano, Florence, and more.
Your home base is the welcoming village of Pancole, where the Sabatini family’s hospitality offers a true taste of Italian life. Daily walks wind through lush vineyards and olive groves, leading to iconic sites and off-the-beaten-path treasures alike. Expert guides share Tuscany’s history and secrets as you explore Siena’s medieval streets and Florence’s Renaissance masterpieces, ensuring every moment is rich with local insight.
This tour package’s unique selling point is its combination of scenic hikes, immersive cultural experiences, and convivial wine tastings that foster genuine connections with fellow travelers. With all accommodation, transport, and meals included, your only focus is to savor Tuscany’s flavors and vistas. If you’re seeking a walking tour that weaves together fine wine, local hospitality, and historical wonders, this journey through the heart of Italy is not to be missed.
8 days
USD 2,775fromUSD 2,692
Step into the heart of Tuscany and experience its timeless beauty on the "Via Francigena: Best of Tuscany" walking tour. Over nine days, this self-guided journey leads travelers along the famed pilgrimage route from San Miniato Alto to Buonconvento, passing through San Gimignano, Monteriggioni, and Siena. Each day’s walk offers a blend of historic hamlets, fortified towers, and rolling vineyards, with achievable daily distances suited for moderately active explorers. Along the way, indulge in regional delicacies like white truffles, Siena’s pici pasta, and saffron from San Gimignano. Evenings are spent in carefully selected hotels and agriturismi, combining authentic hospitality with comfort. The unique selling point: this tour package immerses you in Tuscany’s best food, landscapes, and culture—all along an ancient pilgrimage trail.
9 days
fromUSD 1,290
3% Off Today
For a truly immersive escape into the Tuscan lifestyle, "Local Living Italy—Tuscany San Gimignano" offers a week-long adventure centered in the medieval gem of San Gimignano. This guided wildlife trip invites you to settle into shared accommodations with fellow travelers and a knowledgeable CEO, all while having Rome and Florence at your fingertips.
Venture into the heart of Tuscany: stroll vineyard-laced hills, discover medieval treasures, and embrace your creative spirit amid the region’s rolling countryside. Optional day trips to Siena and Florence add depth for those who want to experience Italy’s cities, while ample free time lets you savor local wines or wander rustic farmsteads.
The unique selling point of this tour package is its focus on forging meaningful connections—with the land, local traditions, and your travel companions. Whether you’re a solo explorer or seeking a communal travel vibe, this trip provides a rare opportunity to live and breathe the authentic Tuscan way of life.
7 days
USD 1,749fromUSD 1,697
13% Off Today
Savor the flavors of Italy on the Italy Real Food Adventure, an eight-day journey for food lovers seeking to uncover the country’s culinary heart. Travel from Venice to Rome, sampling street eats, local wines, and homemade favorites in Tuscany, Bologna, and beyond. Each region reveals its own specialties, from cicchetti in Venice to rustic Tuscan fare and the vibrant food scene in Rome.
This easy-paced tour is led by locals who guide you through markets, vineyards, and kitchens, ensuring you experience both classic dishes and hidden gems. Whether you’re a seasoned gourmand or simply curious, the trip’s USP is its regional diversity—showing you that Italian cuisine is much more than just pizza and pasta.
Perfect for anyone with a passion for food and culture, this tour package promises a journey through Italy’s most delicious traditions.
8 days
USD 3,860fromUSD 3,370
Follow in the footsteps of medieval pilgrims on the "Via Francigena: Lucca to Siena" tour, an 8-day self-guided hiking trip through Northern Tuscany’s enchanting landscapes. Ideal for experienced travelers and seniors with a moderate sense of adventure, this private tour lets you traverse the flat plains of Val d’Elsa, ascend into the Tuscan hills, and explore UNESCO-listed towns such as San Gimignano and Monteriggioni. Comfortable, family-run accommodations and delicious local cuisine enhance each day’s journey. The unique selling point of this tour package is the freedom to experience Italy’s iconic countryside and historic villages at your own pace, steeped in tradition and beauty.
8 days
fromUSD 1,190
Discover the Tuscan countryside and culture on this 8-day self-guided walking tour. Through the extensive footpath network of the area, roughly following the traces of the Via Francigena, one of Europe’s most important ‘highways’ in medieval times, you walk from village to village and experience a full immersion in the world-famous Tuscan landscape. The tour is perfect as an introduction to the region and a great choice for people who love museums, galleries and Gothic and Romanesque architecture. You have plenty of time to visit attractions on most of the days.
You will also have time to visit all the beautiful medieval villages and historic towns along the Via Francigena: starting from beautiful Lucca, you’ll pass through Fucecchio, San Miniato, Gambassi Terme, the stunning San Gimignano with its medieval skyscrapers and Monteriggioni, admired by Dante in his Divine Comedy. An optional detour can bring you to beautiful Colle Val d’Elsa and the tour ends in Siena, arguably the most perfectly preserved medieval town in Tuscany. This tour threads together some of the most attractive towns and villages in Tuscany in an eloquent procession.
However, the emphasis of the tour is to enjoy the countryside, the rolling vineyards, the poppies in spring and the wild cyclamen in autumn. The area north of Siena is an amazing landscape of rolling hills, alternating vineyards and forests, while cypresses line the way leading to the distant farmhouses. Walking here is an unforgettable experience and many of the views have barely changed for hundreds of years.
Accommodation and some meals are included. You spend a night in one of the best agriturismos in Tuscany, and the final night in the heart of Siena, in one of the most characteristic little hotels.
This is a moderately easy tour which is suitable for those who have some experience of walking and a good general physical condition.
8 days
fromUSD 686
11% Off Today
The rolling hills and timeless charm of Tuscany await on the "Spotlight on Tuscany" tour, a 9-day art and architecture adventure through Italy’s most cherished region. Starting and ending in Montecatini Terme, this moderate-activity trip is crafted for those who revel in culture, history, and authentic flavors.
Enjoy a 7-night stay in the renowned spa town of Montecatini Terme, your base for exploring Pisa, Florence, San Gimignano, and Lucca—Italy’s best-kept secret. Learn the region’s history at WWII’s Gothic Line and the Museum of Liberation. Delight in hands-on experiences, from a Tuscan cooking class to cheese tastings at a local farm. Savor world-class wines and the region’s celebrated cuisine, and enjoy free time to wander Florence’s artistic treasures.
With accommodations, transport, and meals included, the unique selling point is the blend of immersive culinary and cultural activities, ensuring each traveler connects deeply with the heart of Tuscany in a single, thoughtfully curated tour package.
9 days
USD 2,369fromUSD 2,119
Set out on a captivating 9-day cycling adventure along Italy’s renowned Via Francigena, from Parma to Siena. Designed for experienced travelers and seniors seeking a moderate challenge, this self-guided bicycle tour traverses the scenic Appennines, medieval towns, and the rolling hills of Tuscany. Visit historic gems like Lucca and San Gimignano, explore ancient churches, and indulge in Parma’s culinary delights. The route is rich in both history and local flavor, offering time to marvel at castles and archaeological wonders. The trip’s unique selling point is its harmonious blend of demanding yet rewarding cycling and immersion in Italy’s most storied landscapes and towns.
9 days
fromUSD 2,290
10% Off Today
Set off on a sun-drenched Mediterranean Coastal Journey from Barcelona to Tuscany, weaving through Spain, France, and Italy over 16 immersive days. This moderate-activity sightseeing tour is ideal for seniors and experienced travelers eager to sample regional flavors—paella in Barcelona, Provençal cuisine in Marseille, and focaccia in Genoa—while exploring iconic sites like La Sagrada Familia and the Tuscan hills. Go beyond the tourist trail by meeting locals and discovering hidden gems in glamorous Monaco and the Chianti countryside. The unique selling point: a carefully crafted journey connecting the best of three Mediterranean coasts, blending culinary delights with cultural insight.
16 days
USD 6,299fromUSD 5,699
See all San Gimignano October 2025 Tours
Top San Gimignano Tour Activities for October 2025
From cultural, religious and historic sites tours to trekking and hiking and others, here are some popular tour activities in San Gimignano with departures in October 2025.
San Gimignano October 2025 Tour Types
Discover San Gimignano October 2025 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
Get a customized trip to San Gimignano in October 2025
Plan a multi-country or regional adventure across San Gimignano in October 2025, with help from a local expert.
Alessandra GalassiTravel Expert in Italy
Danilo CataniaTravel Expert in Italy
Enrico Maria MalacarneTravel Expert in Italy
Elena KyrimiTravel Expert in Greece & Italy
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