I lived in the West Village for a year and it was my favorite neighborhood in all of the city. Everything is walkable, so pack comfortable shoes and just walk around! I'll jump in on the suggestions for Chelsea Market and the highline. At Chelsea Market be sure to hit up Eleni's for a raspberry cupcake and/or Fat Witch for the best damn brownie you'll ever eat. Walk through Greenwhich Village and you'll find amazing shops, cafes, and restaurants. If you like NYC style pizza, John's on Bleeker is legit (although they only sell by the pie, not the slice). In the West Village, favorite spots are Prodigy Coffee, Swine on Hudson (serves food super late), Vin Sur Vingt Wine Bar on 11th, Westville (10th and Hudson). My husband and I lived on Hudson and Leroy and walked down to Westville at least a few times a week for dinner. The food is superb and fast service. Great for before a night out. I can't say enough great things about the West Village, truly. It's such a unique place in that you often don't even feel like you're in a big, bustling city--especially in the mornings. I loved walking over to prodigy in the morning for an Americano, when the shopkeepers were washing off sidewalks and setting up chairs. Where you go to shop will depend on what type of shopping you like. Soho/Chelsea/West Village all have boutiques. You'll want to go uptown for more high end stuff--midtown on up. 5th Ave is very high end and not a good representation of true NYC in my opinion, but it's a nice place to walk if you want to head up to the park afterwards. Have so much fun and soak up this incredible neighborhood!