I went with friends last year, and my friends have been going for the past 3 years. We stay with a buddy who lives close to Louisville. I'm not sure about this, but if you want to sit in the grandstands anywhere, I'm sure it's at least a couple hundred dollars. The nicer sections of the grandstands and the boxseats I would guess start at near $1,000. I can only really speak for the $40 tickets though. And those you DO NOT have to purchase in advance. If I remember correctly, the first race started at around 11-12pm. The main Kentucky Derby race (which is about the 9th or 10th race) started closer to 5pm. We arrived around 10am and had no problem getting a ticket or finding a place to sit down in the infield. As long as you show up before mid-afternoon, I'm sure you'll get a ticket. A few words on the infield. I've heard that turns 1 and 2 are more "family-orientated." The 3rd and 4th turns are generally known as the "party" corners. It's a drunken free-for-all, and is honestly quite disgusting especially if the infield grounds get at all muddy or wet. By about 4:30pm, the port-o-potties are almost unmanageable. There are plenty of betting counters however set up in tents all over the place. My advice would be to get your betting for the 7th-8th-9th etc... races done way ahead of time to avoid standing in line for 30-45 minutes. Also, unless you are near the fence, you will barely see a horse. Watching is mostly done on the Jumbotrons they have set up on the corners. I'm pretty sure that you cannot bring in alcohol. You can bring in chairs/blankets/tarps though to set up your little "station" where you are going to be setting up shop. At least until people get fall-over drunk, they respect your blanket/tarp area. As far as parking, we used the Louisville football stadium parking lot, and from there it was no more than a mile walk to the infield. Another bit of advice. If you can, go to the racing grounds the day before the Derby. There's a bunch of racing. Tickets are less than $10 to get in and you can sit anywhere you want. And you get a "lay of the land" for the next day. I really felt like I was able to soak up more of a horse racing atmosphere the day before the Derby at the grounds. Saturday was just a big party. It's become a tradition with me and my friends to go to the Derby. It's exhausting but it's fun. I can tell that the infield atmosphere is going to eventually wear on me though. Also, the whole thing with Eight Belles last year kind of put me in a funk after the races.