San Gimignano Tours in May 2026
Planning for a trip to San Gimignano during May? We offer 20+ tour packages to San Gimignano departing in May 2026 that have 280+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of San Gimignano on your May holiday.
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10 Best May 2026 Tours in San Gimignano
Join one of these handpicked San Gimignano May 2026 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
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
fromUSD 2,830
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
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
fromUSD 7,667
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
3% Off Today
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
USD 10,850fromUSD 10,525
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
7% Off Today
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
USD 6,025fromUSD 5,602
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 688
3% Off Today
Settle into the rolling hills of Tuscany for an eight-day journey that’s a feast for the senses. The "Discover Tuscany: Culture, Food & Wine" tour invites you to savor the region’s timeless charm, whether you’re a culinary enthusiast, culture lover, or a traveler seeking relaxation.
Over the week, you’ll stay in a welcoming family-run albergo, gaining insider access to both iconic cities—Siena and Florence—and hidden medieval gems off the typical tourist path. Wine tastings at celebrated Chianti vineyards and a hands-on pasta-making class led by local experts let you truly embrace the Tuscan lifestyle.
The tour’s easy pace and small-group format make it ideal for those who appreciate fine food, age-old traditions, and a slower rhythm of travel. The USP? Deep immersion into Tuscany’s culture through authentic local interaction and culinary delights—ensuring every moment is as rich as a glass of the region’s finest red.
8 days
USD 3,375fromUSD 3,274
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Top San Gimignano Tour Activities for May 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 May 2026.
San Gimignano May 2026 Tours for all Age Groups
San Gimignano tours in May 2026 designed for all ages—families, young adventurers, seniors, and everyone in between.
San Gimignano May 2026 Tour Types
Discover San Gimignano May 2026 tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
San Gimignano Travel Styles
Explore San Gimignano with our diverse travel styles! Choose from luxurious tours that pamper you with comfort and elegance, or budget-friendly options that let you experience the beauty of San Gimignano without breaking the bank. Whether you're indulging in fine dining or discovering hidden gems, there's a perfect adventure waiting for you.
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Plan a multi-country or regional adventure across San Gimignano in May 2026, with help from a local expert.
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