New York City is a beautiful city and I have had the privilege of taking 2 separate vacations there.
The first time I went was in the summer. My trip was originally suppose to be a 3 1/2 day trip but due to a tornado in New York (yes a tornado) my flight was delayed until the next afternoon giving me 48 hours in New York. New York can be seen in 48 hours, just don't plan on getting any sleep.
The second time I went was in fall. I loved it even more in fall and I got to spent 4 days on that trip.
Length of trip
It really depends on what you want to do and where you want to stay but you can do New York in 48 hours or you can spend a week. It is really up to what your plans on and everything that you would want to see.
In 48 hours I: Went to MOMA (Museum of Modern Art), Time Square, Yankees Game (they played the Red Sox), Empire State Building, Statue of Liberty/Ellis Island, Financial District, World Trade Center Memorial, NBC Studios, SpiderMan play, 5th Avenue, and ate at a restaurant famous for being frequented by Sinatra (Patsy's). So you can do it all or at least most of it in that time frame.
In 4 days I got to experience a lot more of New York. I did everything again on my second trip besides the Yankee Game and MOMA but I also did a lot more. I got to see and walk through Central Park, Little Italy, China Town, Grand Central Station, Washington Square Park, The Today Show, and saw a play with Nathan Lane, and ate at a lot more places!
Best place to stay
On my first trip I stayed in Time Square, which was great but also expensive. The second time I stayed in Chelsea which was out of the way but also let us explore that part of New York without all the crowds.
My advice to be to find a place the is in your price range and also around most of the things you want to see with subway access. After all you are only in your hotel room to sleep and change.
If you want to be adventurous in your hotel, go up to the top floor and go on the roof if you can. We snuck up on our roof and had the best pictures of New York along with a fun story.
Times to go to attractions
The best advice I can give is to do upper New York City on the first part of your trip. That part is always busy and it really doesn't matter when you go there will always be people. However try to plan your trip to where you are there on a Sunday. Do the Statue of Liberty and Financial District on Sunday morning. There will not be a line at the Statue of Liberty and they you can walk to the financial district and just walk around because not very many people will be there. The market is closed and everyone is at Church. One of the oldest churches is on Wall Street and its a beautiful site. It is also the site where they stationed first responders and set up a command post during 9/11.
Also the best time to see the Empire State Building is at 2am, there are no lines and the city is beautiful at night.
Hidden local attractions
One of the best Italian restaurants that I have eaten at is IL CORTILE in Little Italy. We stumbled upon this restaurant in the middle of an Italian street fair! The street fairs are so much fun and you will always eat way too much.
One of the oldest bars in New York that still fully operate today is a couple blocks away from Washington park. McSorley's Old Ale House. I don't think it has changed much since it opened in 1854 (with the exception of indoor plumbing).
One bar that inspired a popular TV show called "How I Met Your Mother" is called McGee's. If you are a fan of the show you defiantly want to stop by for a cold one. They have the show memorabilia everywhere.
If you are in the mood for a broadway show and comedy act even after you got through with a broadway show, go down the street to Don't Tell Mama. The bartenders and waitstaff perform their monologues,music acts, and comedy performance for the audience. Its a fun time just make sure you tip your waitress. :)
There is also a great burger joint in the back of a really fancy hotel on the upper west side. I can't exactly remember how to get to it but if you want to try it, let me know and I'll ask the group I was with to help me remember.
One more piece of advice
Take the subway and eat bagels! Buy a subway card and put $20 on it and add more if you need it. The subway is a great way to get around new york with a fairly cheap price. Also, New York City has some of the best bagels you will ever eat! Stop by bagel stands every morning for breakfast.
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