A trip is not made of sightseeing alone. The best vacation memories come from what you did, not what you saw.
Take a walking tour of Siena - See the sights of Siena with an art historian, anthropolgist, or other professional guide... » more
Join the evening passeggiata - Stroll with the locals during Siena's popular evening passeggiata, which starts around 4:30pm. It concentrates on Via di Città and the southern arm of Via Banchi di Sopra, but I recommend... » more
Take a cooking class - Learn to make an entire Sienese meal, from antipasti to handmade pasta to dessert... » more
Sample vino in the "Wine Museum" - Siena's massive 16th century Medici fortress was once a symbol of Florence's dominance. Now its brick vaults host the Enoteca Italiana Permanente, a national wine museum where you can taste the exhibits... » more
Visit nearby Tuscan vineyards - From the hills of Chianti to the mighty Brunello vineyards of Montalcino to the cellars of Montepucliano with their Vino Nobile... » more
Shop Siena - From ceramics to wines, hand-woven textiles to handmade torrone sweets... » more
Hike the Chianti hills - Take a day to hike parts of the Via Francigena, the ancient pilgrimage route through Italy... » more
Attend the Palio horse race - The Palio is one of Europe's most famous medieval contests and festivals, a bareback breakneck horse race around the central Piazza del Campo... » more
Day trip to nearby hilltowns - Within an hour's drive of Siena you can visit San Gimigano, the "Medeival manhattan" of stoney towers; Montepulciano, the archetypal hilltown surrounded by Vino Nobile vineyards; Volterra with its Etruscan heritage; Pienza famous for its cheeses; and the Chianti hills coverd in vineyards and castles... » more
Walking tours & activities
Siena tourist information office
Piazza del Campo 56
tel. +39-0577-280-551
Terresiena.it
Also useful:
Museisenesi.org
Comune.siena.it
Sienaonline.it (private)
Sienafree.it (private)
Planning your time in Siena: Though you can see a few of its greatest hits in just half a day, Siena really deserves at least one good, full day.
In fact, Siena's riches of sights really make it hard to do in a single day, so you're better off spending the night here—that way, you can squeeze in some sightseeing on the first afternoon, and some more on the second morning.
Couple that fact with Siena's central location in Tuscany, and it makes a lot of sense for Siena to be one of the overnight stops on your tour of Tuscan hilltowns.
Hotels
Booking.com, Venere.com, GetARoom.com,
Hostelworld.com
B&Bs & Rental rooms
Bedandbreakfast.com, Hostelworld.com, Booking.com, Airbnb.com, Venere.com
Agriturismi (farm stays)
Booking.com, Bedandbreakfast.com, Airbnb.com, Venere.com, Agriturismo.net, Terranostra.it, Agriturist.it, Agriturismo.com
Apartments
Airbnb.com, Booking.com, Venere.com, Rentalo.com, Vrbo.com, Belvilla.org, Homeaway.com
Hostels
Hostelworld.com, Hostelbookers.com
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Tours of Siena
Tours to Siena from Florence
Escorted daytrips from Siena