re: Planning a trip to Boston/NYC. Worth using a trip planner?

I’m guessing it’s your first time. Can’t speak for Boston, but for NYC buy the city pass. It will have all the “must see” attractions at a discount. Do a couple of walking tours too (might be on the pass as well). We did Meat Packing District, Financial District, and one other. It was great to hear about what you would ordinarily just walk by. If you want to do a broadway show you can get discount tickets Saturday morning at the TKTs booth in Times Square. Not every show is sold there, but you’ll probably find something you like. You will need to plan according to the times of tours and shows. NYC is walkable, and we didn’t find the subway too scary (a bit confusing though).