San Gimignano Tours in September 2026
Planning for a trip to San Gimignano during September? We offer 20+ tour packages to San Gimignano departing in September 2026 that have 390+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of San Gimignano on your September holiday.
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10 Best September 2026 Tours in San Gimignano
Join one of these handpicked San Gimignano September 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
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
Experience the rolling hills and vineyard-dotted landscapes of Tuscany on the Tuscany Walking and Wine tour, an easy-paced 8-day journey created for travelers who appreciate the finer things in life. Starting in Pisa and ending in Florence, this walking tour blends scenic rambles with rich cultural encounters.
Meander through Chianti’s renowned vineyards, explore the sun-drenched medieval towns of San Gimignano, Pienza, and Montalcino, and sample some of Italy’s most celebrated wines—Brunello and Chianti among them. Along ancient pilgrimage paths, you’ll savor local cuisine and fresh produce, refueling your spirit as well as your palate.
The trip includes accommodations in carefully selected hotels, transport, and delicious meals, ensuring a seamless Italian experience. The unique selling point of this tour package is the harmonious combination of gentle hiking and gastronomic pleasure, offering access to Tuscany’s scenic beauty and culinary treasures. For those seeking an indulgent yet active escape, Tuscany Walking and Wine is the perfect getaway.
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 an epic pilgrimage across Italy with "The Full Via Francigena" walking tour, taking you from the Saint Bernard Pass on the Swiss border all the way to Rome over 50 days. This comprehensive self-guided journey covers a vast array of landscapes—alpine passes, vineyards, rolling Tuscan hills, and iconic towns like Lucca, Siena, Monteriggioni, and Viterbo. Each day reveals new cultural riches and culinary delights, with overnight stays in atmospheric farmhouses and family-run hotels. The unique selling point: the opportunity to complete the entire Italian Camino, experiencing the full sweep of the country’s history, scenery, and hospitality. For travelers with time and a passion for immersive travel, this tour package promises a once-in-a-lifetime achievement.
50 days
Experience the thrill of cycling across Italy’s historic heartland with the 'Cycle the Full Via Francigena - Aosta to Rome' tour. Perfect for experienced travelers and seniors seeking moderate activity, this 24-day self-guided journey stretches from the alpine St Bernard Pass to the Eternal City. Pedal through the Po River plain, Tuscan vineyards, Umbrian hills, and along ancient Etruscan roads, discovering towns like Parma, Lucca, Siena, and Viterbo. Along the way, savor regional delicacies, sample local wines and cheeses, and revel in the ever-changing scenery. The USP of this bike trip is its comprehensive route—offering a rare opportunity to cycle the entire Via Francigena, blending cultural depth and culinary adventure from the Alps to Rome.
24 days
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Top San Gimignano Tour Activities for September 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 September 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
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San Gimignano September 2026 Tour Types
Discover San Gimignano September 2026 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
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