in 1999, I won a weekend trip for two to Pittsburgh to visit the Andy Warhol museum. Travel had to be completed by the end of the year. I already had plans to depart two weeks later to Chile where I would through the rest of the year. I didn't have enough time to redeem the prize. I entered the drawing by submitting my name on a piece of paper and putting it into a massive fish bowl.
I still enter the online contests, hoping to win something like that again. I travel quite a bit for work, but would still enjoy winning a trip again.