Presumably you are from the US since in the civilised world most people get a month off every year ;)
A relatively simple but interesting and easy-to-branch-from trip would be to hit one of the big Mediterranean cities; say, Rome, Marseille, Barcelona, Mostar, Athens, Istanbul, Tunis, Tripoli, even Cairo. Hang out there for a bit and then take a ferry to another one (or a smaller place). If you get bored of the Med, you can make trips inland.
A relatively simple but interesting and easy-to-branch-from trip would be to hit one of the big Mediterranean cities; say, Rome, Marseille, Barcelona, Mostar, Athens, Istanbul, Tunis, Tripoli, even Cairo. Hang out there for a bit and then take a ferry to another one (or a smaller place). If you get bored of the Med, you can make trips inland.