Nick,
Good news is that you can plan and track prices 7 months in advance. More good news is that there are 2 international airports in the area..JFK and EWR...(LGA is a bootleg airport).

Pizza would be able to give you the best advice about everything.

There are now legit Bed and Breakfast spots all over NYC. Also look into hotel rates/B&Bs in Jersey City,NJ , as it's only a path train ride away from Manhattan ...but a place actually in NYC would be best bet as with a a 7 day unlimited Metro Card...you can go all over the city.


I'm assuming when you say Florida...you mean to Miami. Again..between the three area airports in the area.....you can start tracking ticket prices and score a really good deal.

I wouldn't suggest taking a bus from NYC to Miami unless you just want to absorb American scenery.But Grey Hound or one of the smaller carriers surely has that route...with several stops.


Train from NYC to Miami?
Look out for Pachanga and Benny Blanco(from the Bronx)



I'm sure there are sites and apps that track and graph flight prices, or you can just randomly do it yourself...but trust me..with that much time to plan....just figure out the most you are willing to pay...and just jump on the ticket when it becomes available for that price.(from a real airline, that is)