Take the Circle Line boat ride around Manhattan, gives a nice perspective of the enormous size of the city. Sailing under the Brooklyn, George Washington, Wiiliamsburgh, and other really cool to look at bridges is quite a marvelous experience. Not to mention seeing the Statue of Liberty, and the downtown Manhattan skyline. As far as dining, as others have said around Times Square is very touristy. Taking in the Times Square scene is a must, as well as seeing a Broadway show (you can get same day tickets 1/2 price at the TKTS booth - there's a long line), but I would find out of the way special places to eat. Yelp actually is a decent way to track down restaurants of which there are many, that are of outstanding quality. Zagats is also a great way to find them. Let's put it this way, there are over 20,000 restaurants in New York City, so it pays to do some research. The area south of Houston street in Nolita and Soho has lots of really nice and not that expensive restaurants and is also a cool place for a stroll. Go for a walk down 5th Avenue starting at 59th street and see Rockefeller Center. Shop at small boutiques if you like in the village (greenwich village) and Soho, check out the large department stores such as Macy's 34th Street, Bloomingdales 59th on the east side, Saks 5th avenue across from Rockefeller center, if you want to drop some serious coin try Bergdorf Goodman across from the Plaza Hotel (which is mainly condos now if you want to really buy a big souvenir - studios start at $1.5 million). See some museums like the Metropolitan Art museum on 5th and 80th, the Guggenheim further up 5th around 89th, the Frick down 5th at 70th and the Museum of Modern Art - the MOMA at 53rd between 5th and 6th. I've lived in the city for 20 years and seen maybe 20% of it, so it's size is just enormous when you count all the boroughs. Take in a game at Yankee stadium in 'da Bronx, too, though it's not the original house that Ruth built, the Bornx bombers are pretty good at scoring runs and the new yankee Stadium is pretty nice, actually a lot more luxurious than the old, gritty Yankee stadium but the old one had so much character. Have fun!!