10 Best Siena Multiday Tours in September 2026

Accommodations

Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Via Francigena: Best of Tuscany - September 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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Via Francigena: Lucca to Siena - September 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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Via Francigena: Southern Tuscany from Siena - September 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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Via Francigena: Walk from Lucca to Siena - September 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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The Full Via Francigena - September 2026

(2 reviews )

No booking fees

Best price guaranteed

One of the most amazing, adventurous, challenging and exciting trips we've ever done. A must for your bucket list.

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

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22% OFF TODAY

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Barcelona to Rome - September 2026

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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

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Super Sales

Tuscany Walks & Chianti Wines - September 2026

No booking fees

Best price guaranteed

The intoxicating beauty of Tuscany is there for all to see. But that’s just the start on this gentle small-group hiking adventure. Guided by an expert tour leader, we experience the Garden of Italy through the eyes of a local, staying in the small village of Pancole, where we’re treated to classic Italian hospitality by the Sabatini family. Our walks take us through beautiful vineyards and we explore the Renaissance cities of Siena and Florence with expert local guides. Of course, we also sample several varieties of the local chianti together, forging friendships that could last a lifetime.

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

18-99 yrs

Operated in

english

Destinations

Siena

Duration8 days

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Siena Tours in September 2026

Get a customized trip to Siena in September 2026

33 Trips in Siena during September 2026 with 406 Reviews

Via Francigena: Best of Tuscany - September 2026

Via Francigena: Lucca to Siena - September 2026

Via Francigena: Southern Tuscany from Siena - September 2026

Via Francigena: Walk from Lucca to Siena - September 2026

The Full Via Francigena - September 2026

Barcelona to Rome - September 2026

Tuscany Walks & Chianti Wines - September 2026

33 Trips in Siena during September 2026 with 406 Reviews

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Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

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Special interests and hobbies

Siena Tours in September 2026

Get a customized trip to Siena in September 2026

33 Trips in Siena during September 2026 with 406 Reviews

Via Francigena: Best of Tuscany - September 2026

Via Francigena: Lucca to Siena - September 2026

Via Francigena: Southern Tuscany from Siena - September 2026

Via Francigena: Walk from Lucca to Siena - September 2026

The Full Via Francigena - September 2026

Barcelona to Rome - September 2026

Tuscany Walks & Chianti Wines - September 2026

33 Trips in Siena during September 2026 with 406 Reviews