My two cents having lived here for years now. Yankee Stadium: If there's not a specific game you're looking to go to, and I would think only the BoSox or Mets would be ones you would specifically look at, I would try to go there on a weekend instead of a weekday. The times I've been there on the weekdays a larger portion the crowd has been more of the corporates going to the game as a business meeting. The bleachers are fun, but dry. I wouldn't sit in the left field bleachers under any circumstances. The seats are just too far away. The right field bleachers bring in the rowdier crowd anyways, and they're the fans who take attendance of the Yankees players in the top of the first, which is always fun to see. If you want to drink and still want the bleacher atmosphere try to get seats along the first base line so you can listen and see all the ruckus from the bleachers but still drink $8.75 beers. Also there's no signature food item. The only good thing is they let you bring food in from outside, so you're not limited to what's inside the stadium. Aside from that I'll echo that it's nothing special. Shea Stadium: Nothing special to see. You'll deal with planes flying into and out of LaGuardia the entire game, so be prepared for that. I actually don't mind the upper deck seats at Shea if you're looking for a cheap option. I've sat there and the bleachers and would prefer the upper deck actually. I don't remember if you can bring food into Shea. The fans seems to come live for the Yankees, Braves, and Phillies. In general if you can find Yankees-Mets tickets at either stadium those are good buys. I've been to those games at both stadiums and paid simiar prices to what you would find on Stubhub for weekend games at Wrigley. The City: I'll echo that Times Square, Empire State Building, etc aren't that exciting, but if you want to "check the tourist box" then feel fre. I would absolutely recommend checking out Ground Zero though. It's hard to walk by Sears Tower and imagine it not being there, but it hit's you quickly when you go to Ground Zero and see a giant hole in the ground where the equivalent of two Sears Towers used to stand. The other thing I generally tell people is try to head to a comedy club here. Caroline's on Times Square pulls in some decent names, but even some of the smaller venues have funny people performing every night. Aside from that I'm one of those people that JCF referred to about not going above 14th Street, at least on the weekends. I lived in Midtown for three years and never understood that mentality, but after moving to Little Italy I found out what people meant. Head to East Village, the Lower East Side, Greenwich, Village, West Village, Tribeca etc and just walk around - grab some random food, drink a few beers, do some random shopping. For Roast, Garwilly, and any others who want recommendations feel free to PM me. I've lived in the city since I moved east and make good use of my time at restaurants and bars here.