New York City Train Station
the cops banged their night sticks on the benches every hour to discourage one from using it as a flop. - Rachel
I have a lot of experience sleeping overnight and working overnight in Penn Station. Penn is very rare in nyc as a safe public place where anyone can work and/or sleep 24/7. Clean, not hugely crowded, safe to use a laptop, safe in general, about 10 easily accessible pairs of electrical outlets, fabric chairs, sleeping-friendly 24/7, decently clean/usable free bathrooms.
The main waiting area is always open. There's also a first-class (known as "Acela") waiting area, typically open about 7am-9pm, that you can casually walk into if you look decently mainstream / businesslike. This Acela area is NOT sleeping-friendly (guards will wake you up and, if you don't have an Acela ticket, kick you out), but it has comfier chairs than the main waiting area, and good drinking fountains.
So, back to the main area. The guards usually sweep through the main area once a night, around 3 or 4 a.m., waking up people who are asleep and asking each person to show that he or she has a train ticket -- presumably, a train that he or she is waiting to get on. This can be a New Jersey Transit ticket (most are a few bucks each, and they're undated and untimed so a single one can be used repeatedly).
Think logically if you're buying a NJT ticket for this purpose -- for example, if you want to be in Penn overnight, you must buy a ticket for a line that does not have any service overnight (between about midnight and dawn) but does have service the next morning. (NJT schedule brochures are available next to the NJT ticket machines.)
Ticket details are likely to matter less if you're white and dressed in nice clothes; the Penn guards were fairly consistent about their discrimination as far as I observed in 2001-2003 (rarely giving my ticket more than a glance, but carefully inspecting tickets shown by non-whites... and being more rough when waking up non-whites and also people whose clothes suggested homeless/hippie).
If you prefer, you could just take off when the guards show up for their sweep and then come back sometime after."
"Pretty certain that the woman who mentioned Grand Central meant Penn Station: Grand Central closes tight (you can be bold and lounge about in the reception area at the Hyatt next door, though), whereas there is a waiting area at Penn, which is pretty strictly policed: periodically the cops would rap their nightstick on my shoes just like in the old movies and ask for my ticket; people with none would get shooed off (and eventually return of course). It is fairly weird as well: the night I was there (waiting for the Night Owl to come in, which it did an hour late) in addition to the typical homeless and intoxicated persons, there was a rather attractive young lady who spent the night playing with herself noisily; I didn't know whether to be relieved or disappointed when she was run off. "
Plan Trip to New York City
Ramada New Yorker Hotel - I've stayed here several times over the years. Great location across from Penn Station! Close to Macys, Empire State Building and two subway lines outside the hotel.