I've won 2 times!!! The first was through my local phone company in 1999. I won a 7-day land/sea vacation for 4. It included air, hotel, WDW tickets, transfers, and the cruise!!! We stayed at the Dolphin. We received a Cat 4 (family stateroom) for the cruise, but when we got there we were upgraded to a Cat 2!!!!
That was my first trip to WDW and my first cruise and was the start of something big!!! We have been to WDW more times than I remember since then, to
Disneyland 3 times, and on 6
DCL cruises. And I joined DVC in 2001. That contest created a monster!!!!
This past year I won a 4-day DCL cruise for 4 through my local newspaper. It included airfare, transfers and a Cat 11 stateroom on the Wonder. Being a DVC member, I paid a little extra for special airfare arrangements and we went to WDW for 3 days after the cruise and stayed at VWL.\\\\\
I enter about every contest I see for anything Disney (told you I'm hooked!)
One tip.... if you win, collect documents right away for the actual cost if you planned the trip yourself. That way you can claim the fair market value of the trip rather than the inflated amount from the contests sponsors when it comes times to claim the winnings on taxes.
GOOD LUCK on your contest entries!!