10 Best Siena Multiday Tours in October 2025

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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11% OFF TODAY

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

11% OFF TODAY

Duration9 days

From

USD 2,369

USD 2,119

Saving

USD 250

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Italy City Break - 5 Days - October 2025

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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Super Sales

Treasures of Italy - October 2025

4.3

(7 reviews )

No booking fees

Best price guaranteed

TRIP WAS GOOD

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Perugia, Siena, Fl

Rome, Venice, Perugia, Siena, Florence, Genoa, Milan, Verona

Duration13 days

From

USD 1,901

USD 1,844

Saving

USD 57

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Discovery of Italy: 8 Days - October 2025

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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Amazing Italy - October 2025

(3 reviews )

Trip customizable

Best price guaranteed

Absolutely incredible! Italy’s history, food, and charm blew us away. The small group setting was perfect, and everything was tailored for Canadian travelers. Highly recommend!

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

english

Destinations

Rome, Florence, Verona, Sorrento

Rome, Florence, Verona, Sorrento, Venice, Perugia, Naples, Salerno, Siena, Genoa, Milan

Duration15 days

From

USD 2,729

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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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Explore Italy - 4 Days - October 2025

(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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Super Sales

Roman Holiday - October 2025

4.5

(2 reviews )

No booking fees

Best price guaranteed

Everything was good, no complains. the tour guy Antonio was amazing. we are happy with all.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Siena, Florence

Duration8 days

From

USD 1,055

USD 1,023

Saving

USD 32

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Super Sales

The Essential of Italy - October 2025

4.6

(12 reviews )

No booking fees

Best price guaranteed

This trip was incredible….A perfect balance of guided informational tours and free time for exploring your interests. The areas of Italy included were connected thoughtfully with stops in smaller villages between larger metropolitan cities. This divided the travel time into short segments and made the trips between cities enjoyable. We were greeted at the airport with enthusiasm and roses by Joseba and Maxie. Joseba provided us with great advice and then was with us with local Rome expert Mano for a lovely day. For the remainder of the trip our guide Jon was fantastic He was knowledgeable and flexible and fun The trip could not have been better and exceeded all expectations Europomundo made quite an effort to begin this travel season with our tour of Italy and we couldn’t be happier We highly recommend their company and will travel with them again.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Venice, Siena, Florence, G

Rome, Venice, Siena, Florence, Genoa, Milan, Verona

Duration11 days

From

USD 1,577

USD 1,530

Saving

USD 47

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Super Sales

The Essential of Italy end Milan - October 2025

4.3

(6 reviews )

No booking fees

Best price guaranteed

Hi, I really enjoyed this trip. I would suggest to put just two stops/visits for each day and not more: otherwise this could easly cause daley during the tour.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Milan, Rome, Siena, Florence, Genoa

Duration9 days

From

USD 1,248

USD 1,211

Saving

USD 37

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22% OFF TODAY

Super Sales

Barcelona to Rome - October 2025

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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Super Sales

Tutta Italia To Sicily by Plane And Aeolian Islands - October 2025

No booking fees

Best price guaranteed

Travel from Rome to Palermo on the Tutta Italia To Sicily by Plane And Aeolian Islands trip, an 18-day sightseeing adventure tailored for seniors. This easy-paced group tour explores Taormina, Verona, and several other Italian treasures, blending city strolls, cultural sites, and scenic landscapes. With all logistics—including comfortable accommodations, transfers, and meals—handled for you, the journey prioritizes relaxation and discovery. The tour’s standout feature is its inclusion of the enchanting Aeolian Islands, offering a tranquil Mediterranean escape alongside Italy’s classic cities.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Palermo, Venice, Milazzo

Rome, Palermo, Venice, Milazzo, Taormina, Agrigento, Siena, Florence, Genoa, Milan, Verona

Duration18 days

From

USD 3,386

USD 3,284

Saving

USD 102

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Super Sales

Tutta Italia With Beautiful Campania and Sicily - October 2025

No booking fees

Best price guaranteed

Experience an enchanting blend of Italy’s celebrated cities and southern gems on the Tutta Italia With Beautiful Campania and Sicily tour. Over 17 leisurely days, seniors will traverse from Rome to Palermo, visiting Venice, Siena, and Palermo plus nine other scenic stops. This easy-paced city sightseeing tour includes all the essentials—accommodation, transport, and meals—so you can focus on enjoying Italy’s art, cuisine, and culture. The unique selling point is its inclusion of both Campania’s coastal beauty and Sicily’s distinct heritage, creating a truly well-rounded Italian adventure.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

15-99 yrs

Operated in

english

Destinations

Rome, Palermo, Venice, Perugia

Rome, Palermo, Venice, Perugia, Naples, Salerno, Taormina, Siena, Florence, Genoa, Milan, Verona

Duration17 days

From

USD 3,030

USD 2,939

Saving

USD 91

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All Siena Tours in October 2025

22 Trips in Siena during October 2025 with 183 Reviews

22 Trips in Siena during October 2025 with 183 Reviews

Tuscany Walks & Chianti Wines - October 2025

Spotlight on Tuscany - October 2025

Italy City Break - 5 Days - October 2025

Treasures of Italy - October 2025

Discovery of Italy: 8 Days - October 2025

Amazing Italy - October 2025

Local Living Italy—Tuscany San Gimignano - October 2025

Explore Italy - 4 Days - October 2025

Roman Holiday - October 2025

The Essential of Italy - October 2025

The Essential of Italy end Milan - October 2025

Barcelona to Rome - October 2025

Tutta Italia To Sicily by Plane And Aeolian Islands - October 2025

Tutta Italia With Beautiful Campania and Sicily - 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 Siena Tours in October 2025

22 Trips in Siena during October 2025 with 183 Reviews

22 Trips in Siena during October 2025 with 183 Reviews