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I'd go to a travel site and do the 'vacation' selection that includes air and hotel.
Or you can do a cruise. I have a cruise for 2 to Cozumel for 4 days w/ air for only 300 per person.
500 per person, you can almost go anywhere. Go to Southwest Airlines, Airtran, JetBlue and see which one flies out of an airport near you. Then click and see where you want to go.
Well those are the popular times to travel and two long weekends so the chances of finding flights under $250 a person are slim to none to some place warm. Search around you might find a deal but on those two weekends I doubt it unless you want to take a trip to Maine or something.
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