Siena private tours

Welcome to Siena, a city steeped in medieval rhythm where cobblestones lead you to the lively Piazza del Campo. Here, the spirit of the Palio horse race lingers, a testament to competition and community. With a guide, Siena unfolds beyond the Duomo, sharing the tales of its Contrade, the districts that form its heart. Experience Tuscan warmth as you enjoy local tastes on a food and wine tour, while your guide introduces Siena's hidden corners and stories. Each alley and square becomes a chapter in Siena's living narrative, ready for you to explore. If you’re looking for more inspiration, take a look at our curated list of

Welcome to Siena, a city steeped in medieval rhythm where cobblestones lead you to the lively Piazza del Campo. Here, the spirit of the Palio horse race lingers, a testament to competition and community. With a guide, Siena unfolds beyond the Duomo, sharing the tales of its Contrade, the districts that form its heart. Experience Tuscan warmth as you enjoy local tastes on a food and wine tour, while your guide introduces Siena's hidden corners and stories. Each alley and square becomes a chapter in Siena's living narrative, ready for you to explore. If you’re looking for more inspiration, take a look at our curated list of things to do in Siena.

Explore Siena your way

At ToursByLocals, we believe that how you explore is just as important as where you go. That’s why every Siena tour is private, flexible, and built around you: Move at your own pace, skip the crowds, make connections and follow your curiosity. Find local guides offering private tours in Siena for every interest, including:

Food and Drink tours: Learn how pici is rolled by hand in a family trattoria, pair it with ragù or aglione, then sample pecorino and finocchiona at a tiny bottega in the Oca contrada. Cap it with Chianti Classico tastings in a vaulted enoteca off Via Camollia and a stop at Pasticceria Nannini for panforte and ricciarelli.

Layover tours: With 3–5 hours, your guide can meet you at the train station or Piazza Gramsci bus stop, ride the escalators up, and lead a compact loop past Piazza del Campo and the Duomo, with timed entry to the Piccolomini Library if you’d like. There’s time for an espresso and a slice of panforte before a prompt drop-off for your next connection.

History tours: Step into a contrada museum to see Palio banners and hear how each neighbourhood prepares for the race, then view Lorenzetti’s Allegory of Good and Bad Government in Palazzo Pubblico to understand Siena’s civic ideals. Explore Santa Maria della Scala, the former pilgrims’ hospital on the Via Francigena, and find medieval fountains like Fontebranda that kept the city supplied.

The historic centre is very walkable but hilly, and local buses connect the station with the city gates; if stairs or time are a concern, you can book chauffeured tours or ask your local guide about tours with private transportation for station pick-ups, winery add-ons, or nearby villages.

This isn’t a one-size-fits-all itinerary, you can tailor your private tour to match your interests, pace and personality with a local who knows Siena inside and out.

Walking tours & neighbourhoods

Day trip ideas from Siena

From Siena, you can stretch your time with easy day trips to nearby hill towns, vineyards, and art cities, using customizable tours to lean into history, wine, food, or great views.

San Gimignano: Stone lanes, tall medieval towers, and small workshops make this a simple pick if you like history you can see up close, local gelato, and quick stops for photos; your tour can focus on the old town’s quiet corners or a Vernaccia tasting just outside the walls.

Monteriggioni: A tiny walled village that feels like a living postcard, good for a relaxed wander, light walking, and a calm break between bigger stops; pair it with nearby vineyards if you want a short culture hit plus time in the countryside.

Chianti Classico: Curving roads, vineyard views, and hilltop villages like Greve and Castellina suit wine fans and anyone who enjoys simple Tuscan food; tours here can balance tastings with time in small squares and viewpoints without rushing.

Val d’Orcia (Montalcino and Pienza): Rolling hills, cypress-lined lanes, and two towns known for Brunello and pecorino let you mix cellar visits, cheese shops, and scenic pullouts; if you like photography and slower streets, this route fits your pace.

Florence: Big-name architecture, river views, and artisan work in the Oltrarno neighbourhood give you a full art day without living in museums, so you can split time between piazzas, markets, and workshops that match your interests.

A private tour with a local guide is the best way to really get to know a place. Skip the crowds, follow your interests, and see a side of Siena most travellers miss.