10 Best San Gimignano Multiday Tours in September 2026

Get a customized trip to San Gimignano in September 2026

Plan a multi-country or regional adventure across San Gimignano in September 2026, 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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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.

Super Sales

Tuscany Walks & Chianti Wines - September 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 - September 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 - September 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 - September 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 - September 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 - September 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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Via Francigena: Walk from Lucca to Siena - September 2026

(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

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Super Sales

Ultimate Italy - September 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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Cycle the Full Via Francigena - Aosta to Rome - September 2026

(1 review )

No booking fees

Best price guaranteed

An amazing trip, seeing so many different sides of Italy, the main tourist centres, but the rural villages. Fantastically organised and supported when things went wrong (personal injury). Highly recommend this trip for adventurers.

Bicycle toursExplorer

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Turin, Piedmont & Valle d’

Rome, Turin, Piedmont & Valle d’Aosta, Aosta Valley, Aosta, Berceto, Aulla, Massa, Lucca, San Miniato Alto, San Gimignano, Siena, San Quirico d'Orcia, Radicofani, Bolsena, Saint Bernardo Pass, Viterbo, Sutri, Formello, Verres, Viverone, Vercelli, Vigevano, Pavia, Piacenza, Parma

Duration24 days

From

USD 6,850

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17% OFF TODAY

Super Sales

Italian Elegance - September 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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The Full Via Francigena - September 2026

(2 reviews )

No booking fees

Best price guaranteed

One of the most amazing, adventurous, challenging and exciting trips we've ever done. A must for your bucket list.

Walking tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Great St Bernard Pass, Sai

Rome, Great St Bernard Pass, Saint Bernardo Pass, Santhia, Vercelli, Mortara, Garlasco, Pavia, Belgioioso, Piacenza, Fiorenzuola, Fidenza, Medesano, Etroubles, Sivizzano, Berceto, Previde, Pontremoli, Filetto, Aulla, Sarzana, Massa, Camaiore, Lucca, Aosta, San Miniato Alto, Gambassi Terme, San Gimignano, Colle Di Val D Elsa, Monteriggioni, Siena, Lucignano D’Arbia, Buonconvento, San Quirico d'Orcia, Castiglione D Orcia, Nus, Radicofani, Lazio, Bolsena, Montefiascone, Viterbo, Vetralla, Sutri, Campagnano Di Roma, Isola Farnese, Saint Vincent, Verres, Pont-Saint-Martin, Ivrea, Viverone

Duration50 days

From

USD 9,790

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Cycle the Via Francigena - Parma to Siena - September 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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Super Sales

Discover Tuscany: Culture, Food & Wine - September 2026

(5 reviews )

No booking fees

Best price guaranteed

This was an excellent trip. Delivered everything it says in trip name. Visited fabulous locations, learnt interesting facts about each place, tried local food and wine. Magnificent.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Tuscany, Pancole, Siena, Castell

Tuscany, Pancole, Siena, Castellina In Chianti, San Gimignano, Florence, Volterra

Duration8 days

From

USD 3,375

USD 3,274

Saving

USD 101

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Italy Real Food Adventure - September 2026

13% OFF TODAY

Super Sales

Italy Real Food Adventure - September 2026

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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All San Gimignano Tours in September 2026

23 Trips in San Gimignano during September 2026 with 282 Reviews

Get a customized trip to San Gimignano in September 2026

23 Trips in San Gimignano during September 2026 with 282 Reviews

Tuscany Walks & Chianti Wines - September 2026

Via Francigena: Best of Tuscany - September 2026

Spotlight on Tuscany - September 2026

Via Francigena: Lucca to Siena - September 2026

Tuscany Walking and Wine - September 2026

Rome, Florence & Tuscany Family Adventure - September 2026

Via Francigena: Walk from Lucca to Siena - September 2026

Ultimate Italy - September 2026

Cycle the Full Via Francigena - Aosta to Rome - September 2026

Italian Elegance - September 2026

The Full Via Francigena - September 2026

Cycle the Via Francigena - Parma to Siena - September 2026

Discover Tuscany: Culture, Food & Wine - September 2026

Italy Real Food Adventure - September 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 September 2026

23 Trips in San Gimignano during September 2026 with 282 Reviews

Get a customized trip to San Gimignano in September 2026

23 Trips in San Gimignano during September 2026 with 282 Reviews