Ok, so I have a bucket full of points with United that will expire in September, so I'm trying to persuade the wife that this is the year to do Monterey week. Good idea? Thoughts? Experiences? Tips?
I've attended every one for the last 8 or 10 years or so. Each time they are great fun.
My favorite thing is spending all day Saturday at Laguna Seca at the car races. For me it's not so much the races but strolling the paddock there that is most cool. All the cars that are racing (from 1930s Bugattis to Shelby Cobras) are there to walk around, oogle, talk to the owners or drivers etc.
And there are all those chance events that are cool too. It was great fun watching Stirling Moss scare the daylights out of Jay Leno as he "chauffeured" Leno around the track in the 1955 Mercedes SLR he had drove to win the Mille Miglia. In 2006 Toyota, who was just entering F1, broke the track record with their new F1 car (Ricardo Zonta at the wheel). A couple of years ago, I spent over 30 minutes talking one-on-one with (an apparently bored!) Pierre Henri Raphanel about being the Bugatti test driver for the Bugatti Veyron SS speed record. YMMV, but I always have fun at Laguna Seca.
We share a Turn 5 paddock at the track. By "we" I mean the Ferrari Club, the Porsche Club and the BMW Club. You get to park your car right in the infield. I have always attended with the BMW Car Club (and may do so again this year even if I am successful in acquiring my 328 or 308 since the 2013 BMW Car Club of America "Oktoberfest" immediately follows the Monterey Car weekend). The paddock requires advance tickets, but is a great base from which to venture through the day. (I oogled a lot of Ferraris in the car corral last summer, and I apologize if I drooled on any of them).
The rest of the weekend is amazing too. Lots to do. The Pebble Beach Concours occurs that weekend and is also a cool event (although once was enough for me). There are dinners everywhere, lots of concours and lots of eye-candy everywhere. Everyone hits saturation point and unless you are driving a lime green zebra striped Enzo spewing 4 foot flames from the tail pipe, after a while almost no one bats an eye.
Check out the websites of the "Concorso Italiano", "Monterey Motorsport Reunion", the "Pebble Beach Concours" and "Barrett Jackson'" to get a sense of what the weekend is like.