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Are we talking about surfing or skating?
Since apparently no one has mentionned what wheels and trucks they use, I'll start... (edit: actually, just noticed this isn't true...)
Indy 210s, with old blue Kryptos (80mm) and Abec11 Grippins. I also got Biltin bearings form my Grippins, they are wicked!
LOL. My bad. Ok I have a sector 9 and my buddies and I used to cruise through Aliso Viejo on carve boards because all of the streets are smooth "mac" and long undulating hills. Some runs are 3-4 miles long. We alternate who has to drive the van to run interference for traffic coming up behind us. When we reach the bottom we drive to the top again. Tons of fun.
That sounds awesome, it's the ideal longboarding situation in my mind. The main reasons I don't do it more often are because there's a lot of rough pavement around here or back at home, and lots of steep scary hills without good runouts (I really have no idea how to stop yet, short of bailing). I like long, gradual hills that I can just relax and cruise down, no high speed bombing...
My board is a stock Sector 9 El Camino pintail, probably 48" or so. It should keep me happy for a long time at this rate.