2 of My Favorite Street Sailing Vids

In addition to Andy ripping it up on a short trick board you have the option of using a longboard where the wheels are at the ends of the board. This keeps you from a mis-step, possibly popping the board up and out from under you. Most any generic longboard will due but a board targeted toward carving is the best. It's great for practicing wave technique. This is a great feel good vid. Just two guys having fun on a longboard. (not me, so it is cool)

This an example of what you can do in higher wind. This looks to be a mountain board set up for the pavement. The board is heavier but carvy as anything! You can really try some stuff on a longer wider deck.