...being there, but without the crowds
Watching the Palio from the central part of the Piazza del Campo is free for everyone. A Palio ticket is required to access Siena's balconies, grandstands, windows, which are all private property. Your Palio experience will vary very much according to the viewpoint selected in the piazza del Campo, a selection which should comply with your personal priorities for the day. You should consider if you require more comfort (windows), more action (the grandstands), or maybe a specific viewpoint such as the Mossa (start) or the San Martino bend. Balconies to watch the Palio di Siena aren't more comfortable than granstands, but being balconies a little higher, they might still be your preferred choice. Grandstand are erected directed on the track, very close to the horses and the race.
All Palio tickets always include the view of the Historical Parade (Corteo Storico), which takes place in the Piazza del Campo before the horse race. All viewing positions are assigned, all Palio tickets report a number and they all guarantee a view as described for that specific position (all spots are different from one other, since both the Piazza del Campo and the palazzi in Siena are all quite irregular). My offer of Palio viewing positions, carefully selected during the years spent in Siena, guarantees the best quality within each category. There is no central Palio Tickets box office; I am the one that goes the closest to being it, with the widest and most selected offer of tickets.
During the three days prior to each Palio the Trial Races are run. During the trial races everything looks like on Palio day, and the Square will be totally full. The jockeys will be wearing the colours of their Contradas, and the start is a regular “Mossa”, like on Palio day. The only difference will be in the speed and intensity of the race. Still each Trial Race can rightly be described as a “Little Palio“, as they are very important tests for your horse, your jockey, and their joint reaction to the piazza del Campo.
Starting four-five days prior to each Palio, Contrada Dinners are held. Each Contrada holds them in its own district, open-air in some scenic spot of the Old Town. The dinners are an important moment of the Contradas year, but are also a source of income, fundamental to the Contrada’s activities (Contradas are active all year round, the Palio is just their highlight). For those new to Siena and the Palio, the Contrada Dinners are the best occasion to get acquainted with the complexity of the Palio and of the Contrada of which one is guest (and to the likelihood to get “adopted” by someone...)
I can also find hotel rooms, in some cases in otherwise sold-out properties during Palio days. And I know the best guides, for special Siena (and Palio) tours which go well beyond the Contrada Museum or the Blessing of the Horse. And I always find a table at the best resaturants in town, say at Le Logge, at I Tre Cristi, or Da Divo. Enjoying being in Siena myself does help a lot...