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Experiences on demand · Medieval Tuscany

Private tours in Siena

Five private experiences in Siena and the surrounding Tuscan countryside — the Val d'Orcia, Chianti, San Gimignano.

Led by working scholars Small groups · usually 6 or fewer B Corp certified partner
4.9 / 5 Trustpilot · 4,000+ reviews · Context Travel
Booked in 60+ countries 20 years of private tours
Certified B Corp Doorways' mindful-travel partner

5 private experiences in Siena

Hand-picked from Context Travel's catalog. Every CTA below books direct with Context, no markup, no agency fee.

Staying nearby?

Doorways books the villa

We have 6 hand-picked villas in Siena and the surrounding country, each walked through by us. Pair an experience with a villa week and we'll line up the rest.

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Custom request

Want something not on the list?

A private cooking class with a Michelin chef in Siena. A vineyard with the founder. A truffle hunt in November with the dog who actually finds them. Tell us the brief and we'll have our partner build the experience.

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Experiences are delivered by Context Travel, our B Corp-certified partner. Bookings made through these links may earn Doorways a referral commission, at no additional cost to you. Doorways does not mark up Context Travel pricing.

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