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Originally Posted by Poiseuille
+1 on 9/11 Memorial, if you go there make sure to find the Survivor Tree before you leave.
+1 on Empire State Building, get there as early as you can.
my favorite restaurant (that doesn't require a second mortgage) is 10 mins north of your hotel on W52nd St. between Broadway & 8th Ave. Google "Gallagher's Steakhouse NYC" for menus and details. Best staff, best kitchen and best ambiance you're likely to find. Make reservations before you leave home, you can always adjust +\-30mins once you're in town.
one bit of advice: if you're not well used to the NYC subway system, take cabs. there is Uber, but very limited compared to most cities.
Edit: regarding your question about best way to get from EWR to Times Square, bite the bullet and take a cab. Schlepping luggage around Manhattan is no fun, especially if the weather is bad. Both Uber & Lyft ARE available at the airport, about $50 to midtown Manhattan.
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Honestly, I would skip Empire State. Go to 9/11 memorial. Then walk next door to One World Observatory. Far better views, better experience and saves time. Just buy tickets online and save time waiting in line too. Times square, Rockefeller and pizza should fill a day.
Agree regarding subway. You will waste time trying to figure it out if not used to it. Just uber, plenty of drives and usually never much of a wait for a ride.