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 330+ 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.
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
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
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
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
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
Italy’s rich tapestry unfolds on the "Premium Italy in Depth" walking tour, an expertly crafted 15-day journey designed to balance leisure with discovery. From the historic streets of Bari to the shimmering waterways of Venice, experienced travelers will delight in the country’s cultural and culinary treasures. Highlights include an exclusive audience with a Roman nobleman, overnight stays among the rolling vineyards of Tuscany, and a guided exploration of Pompeii’s ancient ruins. Along the way, savor traditional Italian cuisine, unwind on pristine coastal beaches, and discover charming villages alongside vibrant urban centers. Led by an attentive local guide, this small group tour ensures both comfort and connection, offering unique opportunities to interact with locals and venture off the tourist trail. What sets this trip apart is its seamless blend of must-see landmarks with insider experiences—ideal for those seeking both iconic sites and hidden gems on a truly immersive Italian adventure.
15 days
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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.
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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 May 2027 Tour Types
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