10 Best Siena Multiday Tours in August 2026

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Tuscany Walks & Chianti Wines - August 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 - August 2026

4.6

(26 reviews )

No booking fees

Best price guaranteed

We walked the Via from San Miniato to Buonconvento, a major life experience. The Tuscan countryside unfolds and offers picture-perfect vistas every day. The track is very quiet, some days we would only see one or two other walking groups, so plenty of time for reflection. The days were longer than we expected, we certainly weren't fast walkers, so obviously that plays in, but we did find that some of the stretches were uncomfortably hot, in full sun. Often there was long stretches between water, and not many places to stop. You need to factor this in to your thinking and expectations. We had thought about this in advance and carried sun umbrellas that clipped onto our belts and backpacks so that we could walk with our own shade with hands free to use poles... strongly recommend investment. Some of the accommodations were fantastic, others quirky and fun, and a couple disappointing. Highlights in Gambassi Terme and our last night before Buonconvento.

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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11% OFF TODAY

Spotlight on Tuscany - August 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

11% OFF TODAY

Duration9 days

From

USD 2,369

USD 2,119

Saving

USD 250

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Italy City Break - 5 Days - August 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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Via Francigena: Lucca to Siena - August 2026

4.7

(16 reviews )

No booking fees

Best price guaranteed

Varied hotels en route, all good standard. Smooth delivery of luggage daily. Helpful app.

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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Grand Journey of Italy - 11 Days - August 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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Private Gourmet Wine Tour in Tuscany - August 2026

4.5

(2 reviews )

Trip customizable

Best price guaranteed

What a beautiful time spent in Tuscany on this trip. This was a wonderful tour. Great accommodations! Fabulous wines and meals. We had a wonderful driver, Brando, who was patient and knowledgeable. This is a trip well worth it. Villa Lecchi was elegant and made us feel very special! Spectacular location in the heart of Chianti hills

Food toursWine tasting tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

22-89 yrs

Operated in

english, german

Destinations

Tuscany, Chianti, Florence, Sien

Tuscany, Chianti, Florence, Siena, Pisa

Duration4 days

From

USD 2,840

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Discovery of Italy: 8 Days - August 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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Via Francigena: Southern Tuscany from Siena - August 2026

4.5

(8 reviews )

No booking fees

Best price guaranteed

An amazing walk through the Tuscan countryside. Exceptional organisation and attention to detail meant we could concentrate on having a great time and not have to worry about accommodation, meals and transfers. Thanks!

Trekking and Hiking

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Siena, Lazio, Lucignano D

Rome, Siena, Lazio, Lucignano D Arbia, Tuscany, San Quirico d'Orcia, Castiglione D Orcia, Radicofani

Duration8 days

From

USD 1,260

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Cycle the Via Francigena - Parma to Siena - August 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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Explore Italy - 4 Days - August 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 - August 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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The Tuscan Dream Self-Drive - August 2026

(2 reviews )

Trip customizable

Best price guaranteed

GO!!! Our first time in Italy and this package was absolutely amazing. The price, sights, hotels and people couldn’t be beat. Really, just go!

City sightseeing

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Rome, Siena, Tuscany, Chianti, Pistoia

Duration7 days

From

USD 629

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Cycle the Via Francigena - Siena to Rome - August 2026

4.5

(2 reviews )

No booking fees

Best price guaranteed

The Via Francigena is well signed and has a lot of different scenery, wheat and hazelnut farms, forests old towns etc and great different accommodation each night.

Bicycle tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Rome, Siena, San Quirico d'Orcia

Rome, Siena, San Quirico d'Orcia, Radicofani, Bolsena, Viterbo, Sutri, Formello

Duration9 days

From

USD 2,460

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All Siena Tours in August 2026

18 Trips in Siena during August 2026 with 201 Reviews

Tuscany Walks & Chianti Wines - August 2026

Via Francigena: Best of Tuscany - August 2026

Spotlight on Tuscany - August 2026

Italy City Break - 5 Days - August 2026

Via Francigena: Lucca to Siena - August 2026

Grand Journey of Italy - 11 Days - August 2026

Private Gourmet Wine Tour in Tuscany - August 2026

Discovery of Italy: 8 Days - August 2026

Via Francigena: Southern Tuscany from Siena - August 2026

Cycle the Via Francigena - Parma to Siena - August 2026

Explore Italy - 4 Days - August 2026

Best of Europe - August 2026

The Tuscan Dream Self-Drive - August 2026

Cycle the Via Francigena - Siena to Rome - August 2026

18 Trips in Siena during August 2026 with 201 Reviews

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 August 2026

18 Trips in Siena during August 2026 with 201 Reviews

18 Trips in Siena during August 2026 with 201 Reviews