Okay so a month from now, I arrive in JFK at around 6pm and leave around 5 am the next day. Considering it'll be nighttime:
What is the safest way and cheapest way to get to Grand Central from the airport and back? Uber? regular cabs? some sort of shuttle service? public transportation?
I quite enjoy photography and so this is what I'm most looking forward to do in the city. I want to take pictures of the skyline and from rooftops. Any good locations you can recommend?
I haven't been in New York since I was 20 I have never been in a bar in the city before!!! Any suggestions?
I'd like to stay in Midtown but feel free to suggest anywhere else if you think it's truly worth the trip :)
A lot of great answers here already from everyone! Andy shared good advice as far as transportation goes, and everyone contributed wonderful places to stay/eat/drink.
For photography, I'd definitely suggest taking a walk along the High Line Park (High Line). You'll get some great shots from "above" the city. Just be sure to bundle up (it can get pretty windy over there). I'm thinking that at night, it won't be as crowded there either.
If you want an indoor/outdoor rooftop shot, I would also recommend going to the Meatpacking District (Meatpacking District). You could see if The Standard New York (The Standard) rooftop is open and from there you'll be able to get some nice pictures as well. Otherwise, there are plenty of other (hotel) bars in the area that have rooftops like the Hotel Gansevoort (Gansevoort Hotel).
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First, the airport transportation question. The cheapest way to get to Grand Central will be by public transportation. Fortunately NYC subways are cheap and fast and often will be faster than a cab given the traffic.
After you exit the terminal at John F. Kennedy International Airport, look for signs for the Airtrain. Get to the Airtrain and purchase a metrocard, which is used for all NYC public transportation options (subway, Airtrain, buses). The Airtrain will be $5 and a subway ride will be $2.50. And depending on what else you do that night, put a few more rides on your card just in case.
Now take the Airtrain towards Jamaica Station - Sutphin Boulevard in Queens. Once there, you'll transfer to the E train going into Manhattan. Just keep following signs with a blue E on it and you'll get to the station. It's a bit of a walk so just be patient.
Once you get on the train, I suggest finding a map and studying it. The E train will take you through midtown Manhattan, and will turn South at Penn Station and end at 9/11 Ground Zero Tour. Along the way you can transfer to any of the other subway lines to head to your final destination.
I would not recommend staying in Midtown Manhattan because that's where the offices are and it isn't a great neighborhood for nightlife unless you want to spend a lot of money. For a more casual, fun night out, I suggest going to East Village or West Village. There you'll find a very high concentration of great bars and restaurants. And most places are cheap enough to not break your budget. I won't name all the good bars, but a few of my favorites are McSorley's Old Ale House, Little Town NYC, Death and Company, The Fat Black Pussycat, Fat Cat and Kenka.
As for photography, you won't be short on things to shoot in NYC. But for rooftops, that's a little more difficult. I'll let someone else handle that one.
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Take a shuttle bus from JFK to Grand Central, it costs around $15.
Honestly a cab is a fixed fare from JFK to midtown and is around $50.00 and is easy. Cabs and uber around NYC are reasonable. If you like photos go to Ink48, as the view from their rooftop bar over the Hudson and back towards the Manhattan skyline is incredible. The drinks are great too. A great midtown hotel is Eventi - A Kimpton Hotel you can get a view of the Empire State building with floor to ceiling glass windows so close you can almost touch it. They are not over the top expensive and the hotel staff are so good. The Mermaid Oyster Bar is great in Greenwich Village on a Monday night $1.00 oysters.
I agree that public transit is the easiest and cheapest option. You may want to take a cab when you return since it's the middle of the night.
If you're main priority is photographing the skyline I strongly recommend you do it from Brooklyn. Brooklyn Heights Promenade and One Brooklyn Bridge Park are both great options and they are close together.
From JFK, you can take the air train to Howard Beach and then transfer to the A train toward Inwood - 207th St. Exit at High St. and both are within walking distance.
I'd also recommend you go to Greenwich Village for the nightlife. Andy has great recommendations there. You can easily access it from the same station. At High st., you can take the A train to W.4th St.
If you're really set on Midtown, Bryant Parkoften has a lot going on fairly late and is nice to photograph. You can also easily access it from Greenwich Village by taking a B/D/F/M train from W.4th St.
If you have more time the Flatiron Districtis nearby.
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