@awakemysoul: Okay, cool! I mostly have food suggestions, but I think that’s the best way to get to know a city, so… I hope you enjoy them!
Chinatown is one of my favorite parts of Manhattan. It can be a little grungy in places but the food is often really great. DH and I are really loyal to Nice Green Bo, which is a Cantonese restaurant with great pork dumplings, scallion pancakes and noodle dishes. You can get good dim sum at Nom Wah Tea Parlor, though my favorite dim sum requires a trip deep into Brooklyn. (If you feel like making the trek, it’s East Harbor Seafood Palace in Sunset Park. Aim to arrive around 10 am, otherwise the wait is forever because it’s so packed.) Stop into a Chinese bakery for dessert (just point at what looks good) or have some bubble tea, or an ice cream cone at the Chinatown Ice Cream Factory. (They have awesome flavors like lychee and almond cookie.)
You can also walk over to Little Italy from there. It’s a shadow of it’s former self, but you can get yummy red sauce Italian at Rubirosa, and good pastries at Ferrara.
Shake Shack is a great New York fast food chain. They have a deep-fried cheese-stuffed portobello mushroom “burger” for non-red-meat-eaters, and their shakes are out of control.
If you like oysters, go to the Grand Central Oyster Bar. It’s right in midtown near lots of tourist attractions and is a classic NYC experience. Sit at the counter and get raw oysters, a chowder or pan roast or one of their fried clam or fried oyster sandwiches. Don’t bother sitting in the restaurant portion – the food there is overpriced and not so great – but the counter is where it’s at.
For pizza, I like John’s Pizzeria on Bleecker Street or Lombardi’s on Spring Street. The best pizza ever is at DiFara on Avenue J in Brooklyn, but it’s a full-day sort of thing. If you go, arrive close to opening time or endure a very long wait. If you head out that way, make a Brooklyn day of it and continue on to Coney Island for beach, boardwalk and (if you have any room left) a hot dog from the original Nathan’s.
If the weather is good, walk over the Brooklyn Bridge! And if you’re into biking, you can rent a bicycle on Governor’s Island or at the Brooklyn Bridge Park and bike along protected paths. (Governor’s Island is closed to traffic, so it has incredible views of the city and is a perfect place to bike without worrying about cars.) The island is also a good place for a picnic! There are food vendors there, or you can pick something up before heading over there. The ferry leaves from the pier next to the Staten Island Ferry terminal.
Speaking of the Staten Island Ferry, it’s a nice, free way to see the Statue of Liberty without having to pay for a boat tour. You can just take the ride to Staten Island, enjoy the views, then turn around and head back to Manhattan. If you do that, also check out Battery Park – it’s a nice place to lounge and enjoy a beautiful day.