San Gimignano Tours in May 2027
Planning for a trip to San Gimignano during May? We offer 10+ tour packages to San Gimignano departing in May 2027 that have 120+ 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 2027 Tours in San Gimignano
Join one of these handpicked San Gimignano May 2027 tour packages, tailored to the season.
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
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
14% Off Today
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
USD 2,750fromUSD 2,357
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
3% Off Today
Experience the timeless allure of Italy on the "Premium Sicily and Tuscany" tour, a 17-day sightseeing adventure that journeys from the vibrant streets of Palermo to the enchanting canals of Venice. Designed for travelers with a taste for culture and comfort, this trip uncovers the best of Italy and Sicily’s natural beauty, warm hospitality, and celebrated cuisine. Travel through iconic cities such as Rome and Venice, explore the ancient ruins of Agrigento, and savor exclusive moments like a private visit to a nobleman’s home in Rome. The itinerary features unforgettable highlights, including a scenic drive up the slopes of Mount Etna—Europe’s most active volcano—and hands-on culinary experiences that go far beyond the typical guidebook fare. Throughout your small group journey, enjoy top-tier accommodations, delicious local dishes, and the expertise of knowledgeable guides. The unique selling point of this tour is its curated access to authentic local experiences and off-the-beaten-path encounters, offering a deeper connection to Italy’s living heritage. Prepare to immerse yourself in art, history, and regional flavors on an Italian tour package that promises sophistication, comfort, and lifelong memories.
17 days
USD 10,714fromUSD 10,393
3% Off Today
Embark on the ultimate Italian journey with the "Premium Sicily and Italy in Depth" tour, a 24-day guided adventure for experienced travelers and seniors. Starting in Palermo and concluding in Venice, you’ll traverse the length of Italy, from the volcanic slopes of Mount Etna to the canals of Venice.
Savor local wines at a family-run vineyard, learn to roll pasta like a pro, and explore the marvels of Pompeii and the Tuscan countryside. With three unforgettable Feature Stays and a knowledgeable local leader, this tour package offers a comprehensive immersion into Italy’s culture, cuisine, and history—the perfect Italian odyssey.
24 days
USD 16,870fromUSD 16,364
3% Off Today
From the rolling hills of Tuscany to the sun-drenched shores of the Adriatic, the "Premium Rome to Dubrovnik" trip is a 23-day odyssey through Italy, Slovenia, and Croatia. Explore world-renowned cities like Rome, Venice, and Dubrovnik, marvel at natural wonders like Lake Bled and Plitvice Lakes, and soak in the ambience of ancient towns and coastal gems. This easy-paced, expertly guided itinerary is perfect for those who want to savor Europe’s art, architecture, and cuisine in style. The real highlight? The sheer variety—each day unfolds a new layer of culture, scenery, or culinary delight, ensuring a truly memorable European tour package.
23 days
USD 12,850fromUSD 12,465
See all San Gimignano May 2027 Tours
Top San Gimignano Tour Activities for May 2027
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 2027.
San Gimignano May 2027 Tours for all Age Groups
San Gimignano tours in May 2027 designed for all ages—families, young adventurers, seniors, and everyone in between.
San Gimignano May 2027 Tour Types
Discover San Gimignano May 2027 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.
Get a customized trip to San Gimignano in May 2027
Plan a multi-country or regional adventure across San Gimignano in May 2027, 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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