10 Best San Gimignano Multiday Tours in October 2025

Get a customized trip to San Gimignano in October 2025

Plan a multi-country or regional adventure across San Gimignano in October 2025, 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

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Recommended by

Super Sales

Tuscany Walks & Chianti Wines - October 2025

4.8

(89 reviews )

No booking fees

Best price guaranteed

The trip had a really good balance of activities, with plently to do while still leaving you time to relax and chill out. Tuscany is so beautiful and Fattoria Voltrona was a great place to stay. I would definitely recommend this trip to my friends.

Trekking and HikingFood tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Siena, Tuscany, Chianti, Pancole

Siena, Tuscany, Chianti, Pancole, Florence, San Gimignano

Duration8 days

From

USD 2,775

USD 2,692

Saving

USD 83

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Spotlight on Tuscany - October 2025

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

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Super Sales

Local Living Italy—Tuscany San Gimignano - October 2025

(7 reviews )

No booking fees

Best price guaranteed

Excellent, well thought out tour.

Wildlife

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

12-100 yrs

Operated in

english

Destinations

Rome, San Gimignano, Florence, Siena

Duration7 days

From

USD 1,749

USD 1,697

Saving

USD 52

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Italy Real Food Adventure - October 2025

13% OFF TODAY

Super Sales

Italy Real Food Adventure - October 2025

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

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Mediterranean Coastal Journey Spain, France & Italy - October 2025

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

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All San Gimignano Tours in October 2025

5 Trips in San Gimignano during October 2025 with 96 Reviews

Get a customized trip to San Gimignano in October 2025

5 Trips in San Gimignano during October 2025 with 96 Reviews

Tuscany Walks & Chianti Wines - October 2025

Spotlight on Tuscany - October 2025

Local Living Italy—Tuscany San Gimignano - October 2025

Italy Real Food Adventure - October 2025

Mediterranean Coastal Journey Spain, France & Italy - October 2025

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 October 2025

5 Trips in San Gimignano during October 2025 with 96 Reviews

Get a customized trip to San Gimignano in October 2025

5 Trips in San Gimignano during October 2025 with 96 Reviews

Tuscany Walks & Chianti Wines - October 2025

Spotlight on Tuscany - October 2025

Local Living Italy—Tuscany San Gimignano - October 2025

Italy Real Food Adventure - October 2025

Mediterranean Coastal Journey Spain, France & Italy - October 2025