San Gimignano Tours in October 2026
Planning for a trip to San Gimignano during October? We offer 10+ tour packages to San Gimignano departing in October 2026 that have 380+ 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 2026 Tours in San Gimignano
Join one of these handpicked San Gimignano October 2026 tour packages, tailored to the season.
Tuscany’s rolling hills and Rome’s timeless allure take center stage on the 'Rome and Tuscan Highlights' tour, a 9-day city sightseeing journey that brings your Italian dreams to life. Stay at an agriturismo with hosts Sandra and Antonella, delve into Leonardo da Vinci’s world, and soak in Montecatini’s healing spa waters. Crafted for those who appreciate authentic local flavors and easy-paced exploration, this tour package includes comfortable stays, meals, and guided transport. The unique selling point is the hands-on local immersion, making every moment feel truly Italian. For travelers eager to experience the essence of Tuscany and Rome, this trip is a must.
9 days
Experience the food and fun of Italy on this 12-day guided tour. In Rome, see the Colosseum where gladiators fought to the death, then visit the Vatican Museums with a Local Expert. Travel from Florence to the heart of Tuscany, stopping in scenic San Gimignano for a taste of gelato with a world-champion gelato maker; later, arrive at your hotel for a sampling of the region’s most robust red wines. Prop up the Leaning Tower of Pisa for a photo and see the UNESCO World Heritage Site Cinque Terre with a Local Expert, who will join you for a sea-to-table feast in the medieval town of Monterosso. Allow yourself to be serenaded as you float along the canals of Venice in a traditional gondola, and watch a renowned craftsman blow Venetian glass into a masterful work of art.
12 days
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
Italy’s enchanting backroads come alive on the "Country Roads of Italy, a Women-Only Tour," an inspiring 16-day journey from Rome to Venice. Designed for experienced travelers and seniors, this adventure combines art, culture, and culinary discovery with the camaraderie of a women-only group. Taste the essence of Italy at matriarch-led wineries, sail to the dramatic cliffs of Capri, and learn loom-weaving from women artisans in Perugia. From cocktail classes in Florence to canal cruises in Venice, each day blends hands-on experiences with iconic sightseeing. With accommodation, meals, and transport included, this tour package is not just a trip, but a celebration of Italy’s female heritage and creative spirit. Its unique selling point is the empowering atmosphere and exclusive access to women-run businesses, making it a memorable cultural exploration for those seeking deeper connections and unforgettable moments.
16 days
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
Discover Italy in style on this 12-day guided tour that celebrates the country’s timeless beauty, rich culture and world-renowned cuisine. From the pastel-hued villages of the Ligurian Coast to the Renaissance treasures of Florence and the grandeur of Rome, each moment is exquisitely curated. Sail to Capri and admire the dramatic Faraglioni Rocks before indulging in Michelin-starred dining overlooking the Gulf of Naples. In Assisi, view Giotto’s frescoes with a local historian. Join a hands-on cooking class in Tuscany and in Venice, unlock the secrets of the Doge’s Palace during an exclusive after-hours visit. From hilltop villages to iconic cities, this is Italy at its most indulgent, immersive and inspiring.
12 days
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
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
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
Create lasting memories with your children on the "Rome, Florence & Tuscany Family Adventure," a trip designed for families eager to bond over Italy’s treasures. Explore the myths of Roman emperors at the Colosseum, marvel at the Vatican’s masterpieces, and journey through Siena’s medieval streets en route to Florence.
In Florence, meet Michelangelo’s David, stroll Renaissance avenues, and soak in the magic of the Uffizi. The adventure continues through Tuscany’s iconic vineyards—perfect for parents and kids alike to discover the region’s timeless charm.
This private tour package balances immersive guided experiences with free exploration, ensuring flexible adventures for all ages. The unique selling point: fully customizable options to tailor your Italian journey to your family’s interests, making every day both educational and unforgettable.
8 days
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Top San Gimignano Tour Activities for October 2026
From cultural, religious and historic sites tours to art and architecture and others, here are some popular tour activities in San Gimignano with departures in October 2026.
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Tuscany’s rolling hills and Rome’s timeless allure take center stage on the 'Rome and Tuscan Highlights' tour, a 9-day city sightseeing journey that brings your Italian dreams to life. Stay at an agriturismo with hosts Sandra and Antonella, delve into Leonardo da Vinci’s world, and soak in Montecatini’s healing spa waters. Crafted for those who appreciate authentic local flavors and easy-paced exploration, this tour package includes comfortable stays, meals, and guided transport. The unique selling point is the hands-on local immersion, making every moment feel truly Italian. For travelers eager to experience the essence of Tuscany and Rome, this trip is a must.
9 days
Experience the food and fun of Italy on this 12-day guided tour. In Rome, see the Colosseum where gladiators fought to the death, then visit the Vatican Museums with a Local Expert. Travel from Florence to the heart of Tuscany, stopping in scenic San Gimignano for a taste of gelato with a world-champion gelato maker; later, arrive at your hotel for a sampling of the region’s most robust red wines. Prop up the Leaning Tower of Pisa for a photo and see the UNESCO World Heritage Site Cinque Terre with a Local Expert, who will join you for a sea-to-table feast in the medieval town of Monterosso. Allow yourself to be serenaded as you float along the canals of Venice in a traditional gondola, and watch a renowned craftsman blow Venetian glass into a masterful work of art.
12 days
See all San Gimignano October 2026 travel deals
San Gimignano October 2026 Tour Types
Discover San Gimignano October 2026 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
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