Siena Palio Race

I went to the Palio one time - and it was an amazing week of watching flag throwing practice, marching bands, horses on the track and costumes that got better and more detailed by the day. BUT, it was all on my feet. It isn't easy but my feet forgave me!

I would contact ToursbyRoberto and see if he can help with lodging and event tickets.

Well, you said it already: "pay a bundle for a seat." This event is not that different from being in Times Square NYC for New Year's Eve. Pay up, or don't go. Note that if you wanted to leave early from a high-priced restaurant seat with bathroom access, you probably could not leave - it would be impossible. And it must take quite a while to get "to the exits" after the event. Doesn't sound like fun to me.

We went the day after, and Siena was still pretty busy. We did get to see some Contrada dinner setups still needed, but it would be nice to go to one of those on a non-race day. We could not find the live TV event on the TV at our hotel in Tuscany.

We stayed here https://www.airbnb.com/rooms/13120240?source_impression_id=p3_1681180900_fumqE1p2bGgLg5Fd on the days leading up to Palio in 2017. We did not stay for Palio, but the processions and all of the pagentry were awsome from the balcony! I would even venture to say that the pagentry and the neighborhood celebrations are almost as good as the race. It can't hurt to inquire.

Different city, different Palio, but we were in Asti about a week ahead of their Palio (the oldest in Italy), as they were setting up for the whole week. They set up bleachers and stadium like seating, and sell tickets based on the desirability of the seating, not necessarily based on view, possibly more related to prestige. I would be surprised if Sienna didn't do something similar, but if they don't, and you're not married to Tuscany, Asti and the surrounds were amazing, and less touristy.

More my speed, is the Palio degli Asini di Alba, held on the first Sunday of every October, commemorating a battle in 1275 when Asti was laying siege to Alba, but also to kick off the International White Truffle Fair. Alba is considerably smaller than Asti today, and the pageantry isn't nearly as large as Asti's, but it's a combination of serious tradition, regional rivalry and wonderful absurdity. Probably doesn't involve as much standing or as much competition for seats.

Siena is probably the biggest, it's the most famous, making it likely the largest ask and the most expensive. The pageantry is hours, the race is 90 seconds at most.

I'd guess my recommendation would be to buy a seat for the Asti one instead of Sienna. It's a 350 year older tradition, and I've never eaten better than I did in Piemonte.

Thank you all for the great comments and suggestions. We will take them all into consideration. It was great to hear your ideas.