Hi all,
I finally have my itinerary down and hotel/apartment reservations complete for our August trip. A big thank you to all the Fodorites who helped!

Having spent 3 nights in Montepulciano, we are going to travel from Montepulciano to Greve in Chianti for the next 3 nights, on August 13. I thought this would be a good time to stop in Siena, en route to Greve. I read somewhere that the horse trials for the Palio will be held at 9 a.m. and 7 p.m. (in the three days befor the Palio). Hopefully, we'll get the kids on the road early that morning to see the 9 a.m. trials.

I know that I absolutely do not want to be in Siena during the actual Palio on August 16 (looks to be too much of a madhouse). My question has two parts:
Will the horse trials in the morning let us get the flavor of the Palio without the crowds?
Should I return to Siena after the Palio to get the true sense of the city?

My husband and I were in Siena the day after the Palio in August 2005 choosing that day for the same reason you are - didn't want to face the crowds. And we didn't. It appeared no worse than any well known Tuscan town. But imagine our surprise and delight when, while strolling a side street from the Campo, we were met by a huge parade with members of the winning contrada with all the regalia: flags, drummers, medieval dress, and pacifiers (new birth). We learned later that it had been about 40 years since this particular contrada had won and they were displaying bragging rights in the other neighborhoods. It was one of those unplanned moments that make a lasting memory!

The Palio is Italian theatre at its infamous best - weeks and weeks of rumour and intrigue that amounts to absolutely nothing - it had to be the biggest anticlimax ever - 3.5 hours of waiting in 90oF for 90 seconds of a race that you can't see -

I would well and truely suggest your idea it gives a great insight into the history of the race and the city has a great atmosphere at that time.

Will the horse trials in the morning let us get the flavor of the Palio without the crowds?

Yes

Should I return to Siena after the Palio to get the true sense of the city?

Yes

The very next day, the city is basically back to normal and as toni_g_b says, you will find the winning contrada parading around. It is quite a site.
dave

We have been there during the week b/f
the Palio and walking the back streets
and the city was v. festive - banners
and outdoor dinner tables set up. Really colourful and interesting - but the Palio itself is not for the likes of me - hours in a compound in the broiling sun w/o access to 'facilities'
- no, not for the likes of me! LOL