10 Best Siena Multiday Tours in May 2026

Via Francigena: Best of Tuscany - May 2026

4.7

(34 reviews )

No booking fees

Best price guaranteed

The trip was well organized with some of the hotels on the trip being real gems especially the one in the agriturismo and the one in Monteriggioni. The team was responsive when I had questions both before and during the trip and the app was easy to use. We had a fantastic time and the route was gorgeous.

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

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30% OFF TODAY

Italy City Break - 5 Days - May 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

30% OFF TODAY

Duration5 days

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Via Francigena: Lucca to Siena - May 2026

4.6

(19 reviews )

No booking fees

Best price guaranteed

Amazing experience. It was harder than we expected but we do not regret a moment.

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

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35% OFF TODAY

Grand Journey of Italy - 11 Days - May 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

35% OFF TODAY

Duration11 days

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8% OFF TODAY

Super Sales

Treasures of Italy - May 2026

4.9

(7 reviews )

No booking fees

Best price guaranteed

Regarding the MY TRIP ITINERARY, it will be great if there is an estimate time per location, this can help us plan our own time if we want to do side trips or see other sights on our own and make sure we can get back to the bus on time.

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

8% OFF TODAY

Duration13 days

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35% OFF TODAY

Discovery of Italy: 8 Days - May 2026

(1 review )

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

35% OFF TODAY

Duration8 days

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Via Francigena: Southern Tuscany from Siena - May 2026

4.4

(10 reviews )

No booking fees

Best price guaranteed

Having worked with them on a trip in Northern Italy last year, I was confident they would deliver a great experience. They did. From the quality of the hotels, included meals, the navigation app used down to the distances covered each day, everything was well thought out and first rate. Along the way I met other walkers who’d used other companies. Every single one had a complaint about the company they used. I had no complaints and recommended them repeatedly along the route. I’m already making arrangements for an Italian walk next year with this company.

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

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Amazing Italy - May 2026

(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

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Via Francigena: Walk from Lucca to Siena - May 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

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Cycle the Via Francigena - Parma to Siena - May 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

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35% OFF TODAY

Explore Italy - 4 Days - May 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

35% OFF TODAY

Duration4 days

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8% OFF TODAY

Super Sales

Roman Holiday - May 2026

(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

8% OFF TODAY

Duration8 days

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Cycle the Via Francigena - Siena to Rome - May 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

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

(1 review )

No booking fees

Best price guaranteed

An exhilarating cycle along the full length of the Via Francigena from the St Bernard Pass on the Swiss border to the Eternal City of Rome. The Via Francigena is far more than just a pilgrim trail. Those with more time can discover the full route, cycling this exhilarating and moderately graded bike ride from the Alps to the Eternal City of Rome. Starting from the Great St Bernard Pass on the Swiss-Italian border, you will discover a huge array of spectacular scenery and impressive towns. The route will take you through the vast and fertile Po River plain, across the fast flowing Dorea Baltea river, through stone walled country lanes as you exit the Aosta Valley, over the hills and vineyards of Tuscany, through beautiful Umbrian countryside, down to Lake Bolsena, and finally along ancient Etruscan roads to the impressive city of Rome and St. Peter’s Square. You will discover historic and culturally rich towns of Vercelli, Pavia, Parma, Lucca, San Gimignano, Siena, Viterbo and Sutri, just to name a few. On the way, take time out of your cycle day to visit imposing castles, churches, roman ruins, hilltop towns and vineyards. A trip to Italy would not be complete without delighting in the local food, and this trip does not disappoint. You will eat and drink your way through the best of northern Italian cuisine, visit the gastronomic heaven of Parma in Emilia Romagna, sample the wines and olive oils of Tuscany and indulge in cheese produced in the zones of the cacio di Pienza.

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

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Siena Tours in May 2026

Get a customized trip to Siena in May 2026

32 Trips in Siena during May 2026 with 404 Reviews

32 Trips in Siena during May 2026 with 404 Reviews

Via Francigena: Best of Tuscany - May 2026

Italy City Break - 5 Days - May 2026

Via Francigena: Lucca to Siena - May 2026

Grand Journey of Italy - 11 Days - May 2026

Treasures of Italy - May 2026

Discovery of Italy: 8 Days - May 2026

Via Francigena: Southern Tuscany from Siena - May 2026

Amazing Italy - May 2026

Via Francigena: Walk from Lucca to Siena - May 2026

Cycle the Via Francigena - Parma to Siena - May 2026

Explore Italy - 4 Days - May 2026

Roman Holiday - May 2026

Cycle the Via Francigena - Siena to Rome - May 2026

Cycle the Full Via Francigena - Aosta to Rome - May 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

Siena Tours in May 2026

Get a customized trip to Siena in May 2026

32 Trips in Siena during May 2026 with 404 Reviews

32 Trips in Siena during May 2026 with 404 Reviews