The Amelia Concours is the best classic car event in the country (mind you I'm on the B.O.D.). Much calmer and nicer than the Pebble week IMHO. See
www.ameliaconcours.org for our official schedule of Concours events.
There are a handful of auctions now on the island - RM, Gooding, Bonhams, Russo and Steele and 1-2 smaller ones. Just going to their free previews is a car show in of itself.
Porsche has as big Werks reunion one day too - can't recall if Fri or Sat.
The Concours' big Cars and Coffee event is at the Ritz on Sat, and is free and fun.
Personally, I'm not a fan of the Festival of Speed, that has been at the Omni before.
The actual world class Amelia Concours is Sunday - would try to buy tix in advance, as lines can get insane. Typically >300 of the best vintage and racing cars in the world.
If trouble finding a room - stay in Jacksonville. Maybe 45 min to an hour away.