Get on the horn to your friends. Figure out who's going and how many people you can cram into a single hotel room.
Decide where to go and how much you have to spend to get there. Most warm weather destinations -- Mexico, Rio, the Bahamas, Ibiza -- require flight reservations (not to mention a passport). Why not take a road trip to Florida and Texas? Or head to the mountains for a late-season ski trip.
Research packages, but watch out for scams and hidden costs, such as booking and resort fees and peak week charges.
Budget about $350, in addition to hotel and airfare, for food and activities for the week.