Private tours in Siena
Five private experiences in Siena and the surrounding Tuscan countryside — the Val d'Orcia, Chianti, San Gimignano.
5 private experiences in Siena
Hand-picked from Context Travel's catalog. Every CTA below books direct with Context, no markup, no agency fee.
From$458
Introduction to Siena Tour with the Duomo
A walk through medieval Siena with an art historian — the Duomo, the Campo, the Palazzo Pubblico, the contradas. Why this city stopped in the 14th century and was preserved by stopping.
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Bespoke
Full-Day Tuscany Day Trip from Siena with Wine Tasting
Pienza, Montepulciano, the cypress road outside San Quirico, the abbey at Monte Oliveto Maggiore. The full Crete Senesi day with a local driver and a historian.
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From$483
Siena Palio Tour
The story of the Palio, the horse race that has run twice a year since 1656, told by a member of one of the city's seventeen contradas. The best way to understand why this race matters.
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Bespoke
Full-Day San Gimignano and Volterra Day Trip from Siena
San Gimignano's towers, Volterra's Etruscan museum and alabaster workshops. The medieval-Etruscan double bill of the Tuscan hills west of Siena.
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From$50
Chianti Excursion with Wine Tasting from Siena
Two cantinas in Chianti Classico, a long lunch between them, the SP408 road through the cypresses. A working-vineyard day, with a sommelier driver.
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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.
See Siena villas →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.
Request a custom experience →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.
