Hi S.,
I live in NYC and my daughter is home from college (19). We do all sorts of things together - it's great! We get manicures and then the chair massage while they dry. We eat out at nice restaurants for lunch so it's less and go on Michelin Star searches, as well as, the best hot dog place in NYC (Crif Dog), The real Ray's Pizza, authentic foods etc. You could walk over the Brooklyn Bridge, bring cameras and take pictures all over the city. There's a Hop On Hop Off Water Taxi that goes from S. St Seaport stopping at Battery Park, The Jewish Heritage Museum, The Village and ending (and back) at The Intrepid. Bowling, Chelsea Pier, Off B'Way show, Comedy Club, The PIT is a comedy school and they have show nights less expensive. We run errands together all over the city. There are great movies out like the one with Meryl Streep, Decendants, Mission Impossible and it's great to see them at the Lincoln Square Loews which is like a modern grander version of Graumann's Chinese Theater. The top of the Empire State Building used to have this cool 3D ride in a small theater at the top. The Staten Island Ferry. Bushwick has an art gallery area and so does Chelsea - get the little Art Gallery Guide pamphlet. The museums of course - MET, MOMA, MAD (new and fun!). Ice Skate. You can look up walking tours in NYC and do one of them like a writer's walking tour, foodie walking tour etc. There are great places to eat as you know - Maize/Gordon Ramsey, Le Cirque, Hillstone (best french dip), Felidia, JoJo, Cafe Bouloud, Burger Joint (hidden in the Meridien Hotel), roam around the theater district - tons of restaurants. There's that new sky walkway in the west 20's. Have you seen The WTC Memorial yet? You need a reservation but they're easy to get (you did at first anyway). That's all I can think of now lololol.