The financial district as a whole, especially the blocks near South St seaport are really well lit at night and smooth; some of them are also blocked to traffic. Zucotti Park near the Wall St. bull statue is well lit and has a plaza style surface; as someone mentioned- some of the piers near there have some nice things to skate…etc.
-I have seen a lot of ppl skating at Wash Sq Park late at night. It’s well lit and has the fountain and some trash cans, but of course thousands of tourists and cops too.