10 Best Siena Multiday Tours in September 2026

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 6,150

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The Full Via Francigena - September 2026

(1 review )

No booking fees

Best price guaranteed

We walked the whole Italian Via Francigena and though it was sometimes challenging weather-wise it was a fabulous way to really see and experience Italy. The support and organisation through UTracks was excellent!

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 8,390

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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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Italian Highlights - September 2026

Trip customizable

Best price guaranteed

This Self-drive journey starts from Rome the capital of Italy towards the Siena Area and continues through Orvieto famous for its majestic Gothic Cathedral and the beautiful Perugia region home of the Baci (world-famous chocolate). Drive along beautiful scenic roads in the Tuscan hills. Explore the village of Montalcino and taste the famous Brunello wine. Then you will reach Bagno Vignoni renowned for its spa with a large swimming pool. Visit Pienza famous for its sheep cheese “Pecorino”. Your last stop of the day will be in Montepulciano where you will have the opportunity to taste local wines. Next day, continue your journey through Chianti Landscape, famous for its wines. Driving ahead towards San Casciano Val di Pesa where local oil and wine tasting is scheduled. Then you will reach Florence. The following day, discover Florence, renowned for Piazza della Repubblica, Piazza della Signoria and Ponte Vecchio with its goldsmith's shops. Late afternoon you will depart for Bologna. The next day drives to Parma and enjoys the visit to the vinegar factory in Modena and returns to Bologna. The following day explore Bologna and in the afternoon drive through Ferrara city with a wonderful castle and reach Padua. Next day, Enjoy a visit to picturesque places in Padua: Scrovegni Chapel with Giotto's frescoes, the St Antony’s Basilica, Prato della Valle and Palazzo della Ragione. Next, you will drive to Venice, also known as The Floating City. Sail the Gondola, an iconic Venetian wooden boat and be amused by the Venice lagoon. This itinerary is a perfect example of what you’ll find in Exclusive Italy tours and packages, combining historic cities, culinary experiences, and iconic landscapes into one unforgettable journey.

City sightseeing

Tour Type

Independent Tour

Accommodation

Hotel

Age Range

8-99 yrs

Operated in

English

Destinations

Rome, Venice, Bologna, Siena, Fl

Rome, Venice, Bologna, Siena, Florence, Padua

Duration9 days

From

USD 1,154

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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

Page 2 of 19 Trips in Siena during September 2026 with 210 Reviews

Page 2 of 19 Trips in Siena during September 2026 with 210 Reviews