I just put together an email of nyc suggestions for an acquaintance, and I'm posting it here so that I can share this link with people when they ask for advice.
A great path for a walk from downtown heading uptown would be to walk up through soho on west broadway or Thompson street to Washington Square Park, through the arch and up 5th ave. Make a left on 9th or 10th street (9th street has incredible xmas decorations) and head into the west village (cross 7th ave to bleecker or west 4th st and head uptown). That will get you towards the meat packing district where you can walk on the highline (if it isn’t too cold) into Chelsea.
If you are thinking of going to the top of the Empire State Building, you might consider going to the top of Rockefeller Center instead, it is less crowded, has the same view, and you can look at the Empire state building from Rockefeller center.
Avoid buying gifts/tourist stuff in Times square, you can buy all the same stuff in south Soho, near Canal St/Chinatown for less than half the price.
The big museums are all great, but any one of them is too much for one day. We love some of the smaller museums that you can see in an hour or two – the Frick for paintings, the Cooper-Hewitt for design, and the Morgan Library for antiquities (and the most beautiful room in NYC).
Take a walk through Chinatown/little Italy, but don’t eat at any of the touristy restaurants, they all taste like Olive Garden or worse. Instead, stop in one of the small sandwich shops or Italian delis and get sandwiches or head north of little Italy into Nolita and eat there.
Walk across the Brooklyn bridge unless it is windy and/or raining. Go to Grimaldi’s for pizza. The line moves quickly and it is worth the wait. (This is honestly the one touristy suggestion that is consistently correct in my mind.)
The restaurants on the old part of Stone St in the Financial District are all decent, Ulysses is my favorite and has a good brunch. The restaurants at the sea port are all terrible.
Below are a few of the places I mentioned and more than you need, but I had them all on hand. I would suggest trying to make some reservations ahead of time as these places are all pretty popular. The Blue Ribbon restaurants only take reservations for parties of 6 or more. If you want to do more research, nymag.com is a great place to start.
Hope you guys have a great time. It was nice meeting you in Vegas. Feel free to email if you have any questions or need any more suggestions.
Blue Ribbon/Blue Ribbon Bakery – Lunch/Dinner - One is in Soho, the other is in the West Village. Great gourmet comfort food and my favorite brunch in the city.
Balthazar (Soho), Pastis (Meat Packing, you’ve been), and Minetta Tavern (West Village)– These Keith McNally restaurants are three of our favorites. Balthazar is a Bistro and is quite the scene, the menu is similar to Pastis, good for lunch or dinner. Minetta Tavern is the hottest reservation at town and is more low key than Balthazar and the menu features some incredible cuts of meat. The bone in strip steak is one of the best I’ve ever had.
If you go to Balthazar or if you are in the neighborhood, Pravda is Keith McNally’s Russian Vodka bar with excellent drinks and a great atmosphere– Balthazar followed by Pravda is one of our favorite dates:
Po – dinner - Po is Alex’s favorite Italian restaurant in nyc. It is a hole in the wall in the West Village and it was one of Mario Batali’s first restaurants (though he is no longer involved). Their fresh pastas are amazing and the white bean bruschetta is perfect.
Pearl Oyster Bar – lunch/dinner - Down the street from Po is Pearl Oyster Bar which is a New England clam shack transplanted to the west village. We frequent the restaurant (had dinner there last night). Their lobster roll and fried oysters are as good, if not better, than any I’ve had in Maine.
Blue Hill – dinner - If you are planning on a fancy meal for your date this would be an excellent choice. Alex and I spent our last 5 Valentine’s Days here and our anniversary. The chef, Dan Barber, runs a farm outside of the city which is the source for most of the meat and produce served at the restaurant. This was also the Obama’s choice for their NYC date.
Gramercy Tavern and Union Square Café (you’ve been) – fancy lunch/dinner - Both Danny Meyer restaurants, both great date spots, Gramercy Tavern wins on food, but it can be hard to get a reservation, Union Square Café is not a bad alternative. We love them both and Union Square Café is a frequent request from Alex’s father when he visits.
Aurora – Lunch/Dinner – Casual, inexpensive Italian restaurant in south soho. We go there fairly regularly and can always get a table and have a good, reasonably priced meal.
Jeffrey’s Grocery/Joseph Leonard – These places are around the corner from where we live and are wonderful neighborhood spots with incredible food and atmosphere. Jeffrey’s is particularly great for lunch.
Other places of interest:
Katz’s Deli – the most famous nyc deli, amazing pastrami/corned beef. Don’t be intimidated by the lines, just jump right in or sit down and get waiter service.
Shake Shack – great burgers in Madison Square Park
The Corner Bistro – one of the best burgers in nyc in a classic saloon setting
Les Halles – Meat heavy bistro, made famous by Anthony Bourdain, one location is on John street in the financial district.
Bleecker Street Pizza – my favorite slice in the city, though some people prefer Joe’s around the corner – Joe’s is at Bleecker and 6th ave, Bleecker street pizza is at Bleecker and 7th ave, John’s, a classic nyc whole pie pizzeria is in between.