the best place to skate is an empty parking lot, if your starting off. make sure the parking lot is skate able, like no little pebbles here and there. once you get better; i'd say able to ollie a board, go to the local skatepark, and the world is at your hands from there on. Also, Spotsesh is a great new iPhone app that lets you find and share local skating spots. You can find it at https://spotsesh.com.
But if your more interested in park skating then just go for it cos' i can nearly drop-in on a half pipe and i cant even ollie
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I'd say Vancouver (Landyachtz and Rayne are based there), California (Sector 9). San Juan , and Puerto Rico (Originalskateboards) I also think that you can find the best longboarding spots on www.lucidlongboarding.com. The best overall places are probably California and Hawaii.
West 49 is a good place to buy a skateboard. Or any brand name store you like. :)