Visiting Siena should definitely be on your Tuscan itinerary. Siena's heyday was in the Middle Ages and we're very lucky that the city has maintained its unique medieval character, taking us back in time as we wander down its streets.
To really see what Siena has to offer, spend at least a night here. That way you have at least 2 days to explore the city: you can walk up and down its curving streets and find you've come back around to the same spot, discover great, small restaurants right behind a corner you had passed before and not seen and have time to explore the insides of its imposing palaces.
You can stay in the city to get a chance to both visit Piazza del Campo, have a nice lunch, explore the cathedral (and other sites offered with the same pass), enjoy a delicious, romantic dinner and then turn in for the night. Next morning, climb the Torre del Mangia before exploring the Civic Museum inside the Palazzo Pubblico. You'll have a chance to enjoy and soak the atmosphere of this quaint Medieval town, so different from our usual, contemporary daily lives.
You can also stay nearby outside of Siena and enjoy a bit of both worlds: stay in the countryside with nature all around you, then head in to Siena for day trips and special meals. We've stayed in both bed and breakfasts and hotels in Siena, always finding them very convenient for visiting the sites, resting up and then walking to a nearby restaurant to enjoy delicious Tuscan meals as well as in farmhouses outside that allow for further exploration of the area. We speak from personal experience when we highly recommend spending some time in Siena and its surroundings to experience the special magic of Tuscany!