10 Best Tuscany Multiday Tours in October 2026

Get a customized trip to Tuscany in October 2026

Plan a multi-country or regional adventure across Tuscany in October 2026, with help from a local expert.

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Page 2 of 12 Trips in Tuscany during October 2026 with 54 Reviews

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A Taste of Tuscany Cycling - October 2026

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This is not just a cycling holiday it is an immersion into local Tuscan life, from wine and oil sampling to hot thermal spa baths and the chance to taste local wines and olive oils. Sample the Vino Nobile of Monepulciano, rich Pecorino cheese in Pienza or take a bath in Roman Bagno Vignoni.

Bicycle toursFood tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Tuscany, Chianciano Terme, Radic

Tuscany, Chianciano Terme, Radicofani, Cetona, Chianciano Vecchia, Bagno Vignoni

Duration8 days

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Page 2 of 12 Trips in Tuscany during October 2026 with 54 Reviews

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Timeless Tuscany: A Tuscan Villa Experience - October 2026

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Best price guaranteed

Experience the heart of Tuscany with a gastronomic escape at a historic Tuscan villa. This deliciously curated package includes hands-on cooking and pizza-making classes with the warm and welcoming chef, plus a scenic wine tasting at a local farm near San Gimignano. Enjoy time to relax or explore the nearby medieval gems of Siena and Florence, all while staying in a villa once home to popes and princes. With unforgettable meals, charming towns, and authentic Tuscan hospitality, this is the perfect getaway for food and wine lovers seeking a true taste of Italy

Explorer

Tour Type

Private Tour

Accommodation

Hotel, Villa

Age Range

7-99 yrs

Operated in

english

Destinations

Tuscany, San Gimignano

Duration6 days

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Food, wine, events and nightlife

Adventure and sport

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Tuscany Tours in October 2026

Get a customized trip to Tuscany in October 2026

Page 2 of 12 Trips in Tuscany during October 2026 with 54 Reviews

A Taste of Tuscany Cycling - October 2026

Page 2 of 12 Trips in Tuscany during October 2026 with 54 Reviews

Timeless Tuscany: A Tuscan Villa Experience - October 2026