10 Best Siena Multiday Tours in September 2026

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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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 2,369

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Italy City Break - 5 Days - September 2026

4.5

(4 reviews )

Trip customizable

Best price guaranteed

Exploring Italy through this trip was an unforgettable experience! It allowed us to see all the iconic landmarks in each city we visited, offering a remarkable variety of activities that left no room for boredom. What made the journey even more exceptional were the guides - their passion for the country, combined with their extensive knowledge, made the trip truly unforgettable. They made it a priority to connect with each and every traveler, ensuring that everyone was fully immersed in the tour. With everything taken care of, this trip exceeded our expectations and more. I highly recommend it to anyone who wants to discover Italy in the best possible way!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Assisi

Rome, Florence, Venice, Assisi, Montepulciano, Siena, Tuscany, Bologna, Padua

Duration5 days

From

USD 1,780

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Grand Journey of Italy - 11 Days - September 2026

(2 reviews )

Trip customizable

Best price guaranteed

Awesome tour, Many fantastic sights throughout the tour, great experience I'll never forget. Well organised and good value for money. Thanks for all you do. We really appreciated it.

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Pompeii, Rome, Florence, Venice

Pompeii, Rome, Florence, Venice, The Vatican, Assisi, Montepulciano, Siena, Naples, Sorrento, Tuscany, Bologna, Padua

Duration11 days

From

USD 5,695

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Discovery of Italy: 8 Days - September 2026

4.5

(2 reviews )

Trip customizable

Best price guaranteed

I have had the wonderful pleasure of touring with you, the tour was well executed. The experiences are amazing and very unique. So much fun and I will tour again. I will recommend.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, The Vati

Rome, Florence, Venice, The Vatican, Assisi, Montepulciano, Siena, Tuscany, Bologna, Padua

Duration8 days

From

USD 2,750

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Explore Italy - 4 Days - September 2026

(1 review )

Trip customizable

Best price guaranteed

Our trip was absolutely wonderful! I would like to thank our tour guide, for taking great care of everything. We had something planned every day and the group that travelled with us was so friendly. Everything worked out beautifully. We made memories that will last a lifetime!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-90 yrs

Operated in

english

Destinations

Rome, Florence, Venice, Assisi

Rome, Florence, Venice, Assisi, Siena, Bologna, Padua, Venice & Veneto

Duration4 days

From

USD 1,630

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16% OFF TODAY

Best of Europe - September 2026

4.7

(27 reviews )

No booking fees

Best price guaranteed

The tour was excellent. Sonny was an incredible driver, prompt, friendly and kind. Our tour guide, Callum 'Blinky' Pyper, was full of historical and local knowledge, friendly, patient and kind. Both took very good care of us. We enjoyed all the excursions as they allowed for a bit more interaction with the local cultures.

City sightseeingAdventure

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Budapest, Paris, Rome, London, V

Budapest, Paris, Rome, London, Venice, Berlin, Vienna, Amsterdam, Prague, Pisa, Zagreb, Lucerne, Innsbruck, Heidelberg, Siena

16% OFF TODAY

Duration22 days

From

USD 4,835

USD 4,085

Saving

USD 750

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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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10% OFF TODAY

Best of Western Europe - September 2026

4.7

(17 reviews )

No booking fees

Best price guaranteed

Did alot that I didn't even know existed, like Modena balsamic vinegar...wow. I thought the tour leader was very accommodating for folks with different energy levels .

Art and architecture

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Rome, London, Paris, Heidelberg

Rome, London, Paris, Heidelberg, Lucerne, Innsbruck, Siena

10% OFF TODAY

Duration10 days

From

USD 2,410

USD 2,165

Saving

USD 245

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22% OFF TODAY

Super Sales

Barcelona to Rome - September 2026

No booking fees

Best price guaranteed

Lose yourself in three of Europe's most enchanting countries on this 15-day adventure from Barcelona to Rome. Arrive in the vibrant streets of Barcelona, then travel into the heart of the Spanish Pyrenees. Discover Provencal food and world-class wines as you frolic with Europe’s high rollers in the French Riviera, then feast on breathtaking sights in the cliff-top towns of the Cinque Terre. See master works of art in Florence and get your iconic pic at the leaning Torre de Pisa. Call into beautiful Siena before ending it all in the ancient city of Rome.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Barcelona, Cinque Terre an

Rome, Barcelona, Cinque Terre and Liguria, Florence, Siena, Ribes De Freser, Toulouse, Provence, Nice

22% OFF TODAY

Duration15 days

From

USD 5,680

USD 4,408

Saving

USD 1,272

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A Taste of Tuscany - Hilltop Towns and Vineyards - September 2026

4.9

(9 reviews )

No booking fees

Best price guaranteed

Trip was excellent. Tour Guide, Gus, was fantastic, very knowledgeable, great communicator, and made sure all of our needs were met. Food and wine tour could not have been better. Never really liked many wines but the tastings proved me wrong. The agricultural farms were great and the food fresh and abundant. Villages were quaint. Castle was very interesting - 34 generations living in it and continuously running a vineyard and producing wine since 1141 is unbelievable! Looking into another food tour in another country. Gave accommodations less rating because hotels were in old buildings and they made due with space available: 1) First 2 nights in Hotel Bologna, the room was very, very small and had 2 twin beds aligned in tandem against one wall - would not have fit any other way, 2) Hotel Le Cisterna, last 3 nights, walls were so thin we could hear every word people next door said.

Wine tasting toursFood tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Pisa, Pienza, Siena, Chianti, Vo

Pisa, Pienza, Siena, Chianti, Volterra, San Gimignano

Duration8 days

From

USD 3,040

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All Siena Tours in September 2026

11 Trips in Siena during September 2026 with 156 Reviews

11 Trips in Siena during September 2026 with 156 Reviews

Tuscany Walks & Chianti Wines - September 2026

Spotlight on Tuscany - September 2026

Italy City Break - 5 Days - September 2026

Grand Journey of Italy - 11 Days - September 2026

Discovery of Italy: 8 Days - September 2026

Explore Italy - 4 Days - September 2026

Best of Europe - September 2026

Discover Tuscany: Culture, Food & Wine - September 2026

Best of Western Europe - September 2026

Barcelona to Rome - September 2026

A Taste of Tuscany - Hilltop Towns and Vineyards - 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 Siena Tours in September 2026

11 Trips in Siena during September 2026 with 156 Reviews

11 Trips in Siena during September 2026 with 156 Reviews