Back in 2006, I had won some money and a Caribbean cruise on WOF. I remember it was a week-long Windjammer cruise, which was one of the best trips I had taken. I didn't have a significant other at the time, so I took my dad, and it was a blast. Not just sailing around the Caribbean and swimming, but just relaxing with a cold drink in the shade and, most importantly, our ship was able to dock at some of the smaller islands, allowing us to check out the nightlife. In fact, the hotel they put us up at while we were waiting for our plane back to the US was so nice that both my parents and my wife and I have taken separate romantic getaways there since.
Sadly, I had to study for my comprehensive grad school exams at the time of the cruise, but that's what I did during the day while having fun with everyone else at night. We got to know almost everyone on board, and they were like family by the end of the trip.
With the money, I used it to buy my first decent car, a 2005 Chevrolet Malibu, which was only three years old at the time of purchase. I kept that car until last year, when I finally sold it to my brother, who is still driving it to this day. Thus, I can legitimately tell everyone, "Pat Sajak bought me my first car!"
Anthony