Siena locals take Il Palio quite seriously, so if this is your first time, sit back and observe. Complaints can be taken as criticism, so it’s best to keep comments to yourself, especially during a contrade’s “moment of tension.”
Italians take their time with these things, and there can be up to 20 false starts to the race.
Whether it’s visiting the medieval Tuscan towns of San Gimignano and Volterra, spending some time in Florence an hour away, or just sinking into the Sienese insanity, there’s much to occupy your time and fascination. Don’t think that this is just a one-night event.
For a nice cheap option try the Tre Donzelle, which you must book well in advance. If you arrive to find it full, try the two-star Piccolo Hotel Etruria, which is a few doors down and only slightly more expensive.
Find a balcony for the trials
While it costs a fortune to find a balcony space during the final race, the six trial runs in the three days prior to Il Palio allow you the opportunity to see what the big shots pay for (approximately 10-30 Euros during the trials). Do one trial in the piazza center near the starting line and you’ll see what “jockeying for position” truly means.
Spend the night before the race at a Contrada dinner
For about 60 Euros, you can infiltrate a truly local tradition and have a six-course, open-air dinner with one of the fiercely-local groups and their jockey.
If you fall in love with Il Palio, you can always come back in August.
Book flights into (SAY) as early as possible. As with any city-wide event, the whole town gets slammed and booked long advance. You’ll want to get to the Piazza del Campo up to 5 hours prior to the main event. Even then, you may have trouble finding a place to watch, but you’ll get a good view of the front lines, which will be crowded with perhaps the second-most entertaining part of Il Palio—the fervent residents of each contrade cheering and jeering the horses. Book accommodation a year in advance, and arrive to the race early—like really early—for a chance at a good viewing spot.