I think I'm gonna go with NYC. My company is having a cigar event there on Sept 12, so I figured that would be a good time for me to go on vacation. I think I am going to stay at the Waldorf as the rates are decent. I need food recommendations, and places I should see (besides cigar stores).
Who you are going with will help determine where you should spend your time such as museums, Zoo, and stuff. I would take a gander through Times Square just to check out the lights and action.
1-9/11 Memorial and observation deck. Very well done, but a somber place to be by the fountains and seeing everyone's names
2-Top of the Rock during sunset for great views if you are into that. It really is beautiful.
3-Bronx Zoo if you have kids, they will love it
4-Natural History Museum is my favorite, but Met is also very nice. Met is more art-centric, while the Natural History Museum is more of the recreation of history with diorama exhibits, fossils, beautiful planetarium
5-USS Intrepid is cool if you like aircraft, and want to check out the inside of a carrier
6-Yankee game. Take 4 train from Grand Central, and it stops right in front of the Stadium
7-Met game. Take the 7 train from Grand Central, and it stops right in front of the Stadium
For a great steak dinner, go to Wolfgang's and get yourself the thick cut bacon. Their porterhouse is the main event if you are there with two or more people. Their tomahawk ribeye is also awesome. It is a rip off of Peter Luger's but easily accessible in terms of tables and travel. It is my favorite and I have been to them all. Old Homestead is great too for their garlic bread tower, but the bacon is to die for at Wolfgang's. If you head downtown for the 9/11 Memorial, hit up a late lunch at Katz for their hand cut pastrami sandwich.
For a new phenomenon in street cart food, go over to Halal Guys for a chicken and lamb over rice. Get the white sauce with a little bit of hot sauce. They are on 53rd and 6th. That is the original cart location. Pick the Halal Guys cart with the shortest line as it wraps around the block sometimes. They are expanding to many cities now, and opened a storefront on 14th Street, but for the real experience you should go to the cart and wait online.