10 Best San Gimignano Multiday Tours in October 2026

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Tuscany Walks & Chianti Wines - October 2026

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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Via Francigena: Best of Tuscany - October 2026

4.6

(28 reviews )

No booking fees

Best price guaranteed

Great trip, all happened as planned.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Tuscany, Buonconvento, San Minia

Tuscany, Buonconvento, San Miniato Alto, Gambassi Terme, San Gimignano, Gracciano, Monteriggioni, Siena, Lucignano D Arbia

Duration9 days

From

USD 1,290

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Spotlight on Tuscany - October 2026

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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Via Francigena: Lucca to Siena - October 2026

4.7

(18 reviews )

No booking fees

Best price guaranteed

Beautiful walk. Accommodation was comfortable and breakfasts were good.

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Siena, Lucca, San Miniato Alto

Siena, Lucca, San Miniato Alto, Gambassi Terme, San Gimignano, Gracciano, Monteriggioni

Duration8 days

From

USD 1,190

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Tuscany Walking and Wine - October 2026

4.9

(10 reviews )

No booking fees

Best price guaranteed

Want to explore Tuscany without a rushed itinerary? Want a small group? Want to hike to wineries and hill towns? Stay in interesting hotels that are hundreds of years old? A wine and food buff? Then this is for you. I had a great time on this trip. Had a full day in Sienna and a nice orientation tour of Florence (I spent a few extra days) Plus to get to visit lesser known towns that the big companies overlook. My favorite was Pienza. A nice little town that also had my favorite hotel and great places to eat. And yes, we tasted wonderful Italian wines, as well as the best cold cuts and cheeses I’ve ever tasted. And did I also mention hiking to wineries and hill towns? Wonderful sights, with spectacular views. One hike it rained towards the end, but that didn’t dampen our spirits.

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Florence, Pisa, San Gimignano, T

Florence, Pisa, San Gimignano, Tuscany, Pienza, Montalcino

Duration8 days

From

USD 2,830

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Rome, Florence & Tuscany Family Adventure - October 2026

(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

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Cycle the Via Francigena - Parma to Siena - October 2026

(1 review )

No booking fees

Best price guaranteed

Excellent trip - the bike was great - all hotels also very good with good breakfasts. Was very impressed with the logistics - no dramas!

Bicycle toursSightseeing Tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Siena, Parma, Aulla, Massa, Lucc

Siena, Parma, Aulla, Massa, Lucca, San Miniato Alto, San Gimignano

Duration9 days

From

USD 2,290

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Ultimate Italy - October 2026

(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

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17% OFF TODAY

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Italian Elegance - October 2026

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

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Super Sales

Premium Italy in Depth - October 2026

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

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Super Sales

Premium Rome to Dubrovnik - October 2026

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

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Rome And Tuscan Highlights - October 2026

14% OFF TODAY

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Rome and Tuscan Highlights - October 2026

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

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Country Roads Of Italy, A Women-only Tour - October 2026

6% OFF TODAY

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Country Roads of Italy, a Women-Only Tour - October 2026

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

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Mediterranean Coastal Journey Spain, France & Italy - October 2026

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 2026

16 Trips in San Gimignano during October 2026 with 276 Reviews

Get a customized trip to San Gimignano in October 2026

16 Trips in San Gimignano during October 2026 with 276 Reviews

Tuscany Walks & Chianti Wines - October 2026

Via Francigena: Best of Tuscany - October 2026

Spotlight on Tuscany - October 2026

Via Francigena: Lucca to Siena - October 2026

Tuscany Walking and Wine - October 2026

Rome, Florence & Tuscany Family Adventure - October 2026

Cycle the Via Francigena - Parma to Siena - October 2026

Ultimate Italy - October 2026

Italian Elegance - October 2026

Premium Italy in Depth - October 2026

Premium Rome to Dubrovnik - October 2026

Rome and Tuscan Highlights - October 2026

Country Roads of Italy, a Women-Only Tour - October 2026

Mediterranean Coastal Journey Spain, France & Italy - October 2026

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 2026

16 Trips in San Gimignano during October 2026 with 276 Reviews

Get a customized trip to San Gimignano in October 2026

16 Trips in San Gimignano during October 2026 with 276 Reviews