10 Best San Gimignano Multiday Tours in May 2027

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
Simon H.Travel Expert in Belgium, France, Italy & Switzerland

Start planning your Trip

Recommended by

Accommodations

Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Spotlight on Tuscany - May 2027

No booking fees

Best price guaranteed

Discover the rolling hills of Tuscany, home to sprawling vineyards, charming medieval hill towns, and enchanting cities. Savor a 7-night stay in Montecatini Terme, the famous resort and spa town. Visit Pisa, Florence, and San Gimignano, nestled in the Italian countryside. Discover the charming town of Lucca, Italy’s best-kept secret. Enjoy free time in Montecatini or see the Gothic Line of WWII and visit the Museum of Liberation. Explore the cultural treasures of Florence. Partake in a Tuscan cooking class. Sample cheese at the farm where it is made. Enjoy fabulous local wines and the region’s famous cuisine. Steeped in history, culture and legend, this is Tuscany as you always imagined it.

Art and architecture

Tour Type

Group Tour

Accommodation

Resort, Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Montecatini Terme, Lucca, Floren

Montecatini Terme, Lucca, Florence, Pisa, Siena, San Gimignano

Duration9 days

From

USD 2,119

View Tour

Rome, Florence & Tuscany Family Adventure - May 2027

(3 reviews )

Trip customizable

Best price guaranteed

Hi Stefania! Sorry to take so long to write back. It has been crazy trying to get back into the swing of things at work after that trip. Italy was amazing!! We absolutely loved it! As for feedback on the trip, we really don't have anything that was negative. We loved everything that was planned! We especially loved how you planned the sites that we went and how the pattern flowed (not sure if you did it on purpose but we think so). Also, thank you for being very accessible to us during the whole planning of the trip. You helped put us at ease and it was very reassuring that we chose the right company. That is all that I can given you that might be considered constructive. The rest I could say would just be compliments on everything else. If I can think of anything else that I think is useful I will definitely email you. Hope all is well, Jane P.S. - Does your company only provide trips for Italy or other countries as well, just wondering for the future :)

Food tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Rome, Florence, Tuscany, San Gim

Rome, Florence, Tuscany, San Gimignano, Chianti, The Vatican

Duration8 days

From

USD 7,609

View Tour

Via Francigena: Walk from Lucca to Siena - May 2027

(1 review )

Trip customizable

Best price guaranteed

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.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel, Hostel

Age Range

18-99 yrs

Operated in

English

Destinations

Siena, Tuscany, Lucca, Altopasci

Siena, Tuscany, Lucca, Altopascio, San Miniato Alto, Gambassi Terme, San Gimignano, Monteriggioni

Duration8 days

From

USD 682

View Tour

13% OFF TODAY

Super Sales

Italy Real Food Adventure - May 2027

No booking fees

Best price guaranteed

Italians are the masters of creating simple dishes that burst with flavour. Inspired by nonnas’ kitchens all over the country, this food is regional, seasonal and fresh, and on this eight-day trip through everybody’s favourite culinary hub, you’ll discover that pizza and pasta are only the tip of the iceberg. Uncover the diverse array of unforgettable street eats, meals and cicchetti (small bites) from the postcard-perfect Venice to Rome, where medieval meets modern. Delight in local wine, fresh produce, homemade dinners and seasonal favourites in San Gimignano, Tuscany and Bologna – all with a local by your side – and take your tastebuds on an unforgettable adventure.

Food tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Bologna, San Gimignano

13% OFF TODAY

Duration8 days

From

USD 3,860

USD 3,370

Saving

USD 490

View Tour

Super Sales

Ultimate Italy - May 2027

(34 reviews )

No booking fees

Best price guaranteed

It was a great experience with many highlights throughout our tour. We particularly enjoyed the many immersive stops (i.e. wine tasting, weaving, truffle hunting, pasta making, etc.) in addition to our guided tours. Our tour guide, was very well versed, knowledgeable, and helpful and provided good insights and tips throughout our trip. I can't imagine someone else doing a better job than she did! The local experts were also on top of their games.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Lodge, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Capri, Perugia, Sa

Rome, Venice, Capri, Perugia, San Gimignano, Florence, Rapallo

Duration12 days

From

USD 10,525

USD 10,209

Saving

USD 316

View Tour

17% OFF TODAY

Super Sales

Italian Elegance - May 2027

4.8

(30 reviews )

No booking fees

Best price guaranteed

The guides are the best and make all the difference.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Florence, San Gimi

Rome, Venice, Florence, San Gimignano, Santa Margherita, Cinque Terre, Lake Maggiore, Cortina d'Ampezzo

17% OFF TODAY

Duration12 days

From

USD 5,025

USD 4,169

Saving

USD 856

View Tour

Super Sales

Premium Italy in Depth - May 2027

No booking fees

Best price guaranteed

This is your ticket to explore the best of Italy in just 15 days. From the ancient sites of Rome and visiting one of the Seven Wonders of the World – the Colosseum – to staying in the rolling vineyards of Tuscany to visiting the site of Pompeii with a local guide, this trip encompasses some of Italy's must-do experiences. You’ll visit ancient monuments, lively cities and sprawling vineyards, indulging in delicious traditional cuisine. Kick back on sparkling coastal beaches, get to know the locals and visit lesser-known spots with your knowledgeable local leader – what more could you ask for?

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Venice, Polignano A Mare, Bari

Venice, Polignano A Mare, Bari, San Gimignano, Florence, Nardò, Matera, Naples, Rome

Duration15 days

From

USD 10,715

USD 10,394

Saving

USD 321

View Tour

Super Sales

Premium Rome to Dubrovnik - May 2027

No booking fees

Best price guaranteed

From storied cities to glittering coastlines, uncover the best of Italy, Slovenia and Croatia on a 23-day Premium adventure. Travel through the rustic heart of Tuscany, explore the wonders of Venice, Pisa’s Leaning Tower and visit one of the Seven Wonders of the World in Rome. Discover Lake Bled, the underground world of the Postojna Caves and the spectacular Plitvice Lakes National Park. Take in ancient riches on Korcula island and stroll the legendary streets of Dubrovnik. Throw in expert local leaders, plenty of sunshine and some of Europe’s best food and you have an adventure to remember.

Art and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Dubrovnik, Rome, Bled, Rovinj, P

Dubrovnik, Rome, Bled, Rovinj, Plitvice Lakes National Park, Zadar, Split, Korčula, San Gimignano, Florence, Venice

Duration23 days

From

USD 12,850

USD 12,465

Saving

USD 386

View Tour

Super Sales

Premium Sicily and Italy in Depth - May 2027

No booking fees

Best price guaranteed

Traverse from top to toe of Italy's 'boot' and explore ancient ruins and iconic sites. Eat your weight in pasta and tuck into giant piazzas as you get lost in Venice and find yourself in the Tuscan countryside. This 24-day trip will take you to all the best spots and teach you all the most important parts of Italian culture – like how to roll pasta like the pros! Visit Mount Etna, as you drive up the northern flank of the volcano and take a walk through the spectacular Valle del Bove. Visit a family-run winery, learn about ancient Pompeii, visit Rome’s famous sites and write home about your three amazing Feature Stays – all with a local leader by your side.

AdventureSightseeing Tours

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Venice, Palermo, Bari, Nardò, Ma

Venice, Palermo, Bari, Nardò, Matera, Naples, Rome, San Gimignano, Florence, Marsala, Agrigento, Siracusa, Catania

Duration24 days

From

USD 17,095

USD 16,582

Saving

USD 513

View Tour

14% OFF TODAY

Super Sales

Rome and Tuscan Highlights - May 2027

4.7

(51 reviews )

No booking fees

Best price guaranteed

I chose this trip because of the 6 nights in Tuscany - Montecatini Terme. Cinque Terre, Lucca, Siena and San Gimignano were highlights of this tour. The food for the special dinners was amazing. Rosella and Massimo kept things on track. Organizing and coordinating tickets, transportation (2 ferries, train and bus) and firsthand knowledge of the areas visited was well exhibited by Rosella. The specialty tour guides were knowledgeable and added extra flair to the excursions. Enjoyed the trip immensely.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Montecatini, Florence, Vin

Rome, Montecatini, Florence, Vinci, San Gimignano

14% OFF TODAY

Duration9 days

From

USD 2,750

USD 2,357

Saving

USD 393

View Tour

Country Roads Of Italy, A Women-only Tour - May 2027

6% OFF TODAY

Super Sales

Country Roads of Italy, a Women-Only Tour - May 2027

4.7

(3 reviews )

No booking fees

Best price guaranteed

It was great traveling with other women. I felt some days were too busy, especially the miles we went one day for 45 minutes at a spare. Really enjoyed the meals.

Adventure

Tour Type

Group Tour

Accommodation

Hotel, Villa, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, San Gimignano, Luc

Rome, Venice, San Gimignano, Lucca, Parma, Sorrento, Todi, Perugia, Florence

6% OFF TODAY

Duration16 days

From

USD 7,225

USD 6,775

Saving

USD 450

View Tour

Mediterranean Coastal Journey Spain, France & Italy - May 2027

No booking fees

Best price guaranteed

Venture along the glittering Mediterranean coast on an immersive journey connecting the Spanish, French and Italian Rivieras. Taste your way along the Mediterranean coast sampling traditional Catalan specialties in a 17th-century farmhouse, flavorful Provençal cuisine in Marseille, and traditional focaccia in Genoa. Enjoy the iconic must-sees and venture to gems off the beaten path, like the rolling hills of the Tuscan countryside. Take a step into the culture and meet the locals. From chameleonic Barcelona to sun-kissed Nice; from glamorous Monaco to the rolling hills of the Chianti countryside, find your dream Mediterranean journey.

Sightseeing Tours

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

1-99 yrs

Operated in

english

Destinations

Barcelona, Tuscany, Nice, Genoa

Barcelona, Tuscany, Nice, Genoa, San Gimignano, Costa Brava, Figueres, Marseille

Duration16 days

From

USD 5,499

View Tour

Super Sales

Premium Sicily and Tuscany - May 2027

No booking fees

Best price guaranteed

Make your way to the Mediterranean to discover all the natural beauty, warm hospitality and cuisine Italy and Sicily have to offer. On this 17-day adventure, you’ll travel from Rome to postcard-perfect Venice. From visiting one of the Seven Wonders of the World – the Colosseum – to driving up the flank of Mount Etna, Europe’s largest active volcano, this trip goes the extra mile to deliver experiences that go beyond the guidebooks. Visit the famous spots like the Spanish Steps and Trevi Fountain, then go off the path to a local’s favourite restaurant. Get ready to tuck into local eats, explore iconic sites and brush up on your ancient history, all with an experienced local by your side.

Sightseeing ToursWalking tours

Tour Type

Small Group Tour

Accommodation

Hotel, Resort, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Palermo, Rome, Chianti, San Gimi

Palermo, Rome, Chianti, San Gimignano, Florence, Venice, Marsala, Agrigento, Siracusa, Catania

Duration17 days

From

USD 10,960

USD 10,631

Saving

USD 329

View Tour

Super Sales

Premium Rome to Split - May 2027

No booking fees

Best price guaranteed

Embrace the cultural, culinary and natural delights of Italy, Slovenia and Croatia on a 16-day Premium adventure. Travel through the rustic heart of Tuscany, explore the wonders of Venice’s Piazza San Marco and Pisa’s Leaning Tower and visit the home of a Nobleman in Rome with an expert local leader. Discover the waters of Lake Bled and the underground world of the Postojna Caves. Ride the cable car up Mt Vogel for views over Lake Bohinj and appreciate the caves and waterfalls in Plitvice Lakes National Park. Coloured by sunshine and flavoured with local wine, this pocket of Europe is a joy to explore.

Culture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Split, Rome, Bled, Rovinj, Plitv

Split, Rome, Bled, Rovinj, Plitvice Lakes National Park, Zadar, Chianti, San Gimignano, Florence, Venice

Duration16 days

From

USD 8,980

USD 8,711

Saving

USD 269

View Tour

All San Gimignano Tours in May 2027

14 Trips in San Gimignano during May 2027 with 122 Reviews

Get a customized trip to San Gimignano in May 2027

14 Trips in San Gimignano during May 2027 with 122 Reviews

Spotlight on Tuscany - May 2027

Rome, Florence & Tuscany Family Adventure - May 2027

Via Francigena: Walk from Lucca to Siena - May 2027

Italy Real Food Adventure - May 2027

Ultimate Italy - May 2027

Italian Elegance - May 2027

Premium Italy in Depth - May 2027

Premium Rome to Dubrovnik - May 2027

Premium Sicily and Italy in Depth - May 2027

Rome and Tuscan Highlights - May 2027

Country Roads of Italy, a Women-Only Tour - May 2027

Mediterranean Coastal Journey Spain, France & Italy - May 2027

Premium Sicily and Tuscany - May 2027

Premium Rome to Split - May 2027

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All San Gimignano Tours in May 2027

14 Trips in San Gimignano during May 2027 with 122 Reviews

Get a customized trip to San Gimignano in May 2027

14 Trips in San Gimignano during May 2027 with 122 Reviews