One day in 1960, Bill Gaines called a general meeting of staff, writers, and artists -- in all about twenty men.  Assembling them in his office, he distributed guide books to Haiti and told them they would soon be going on an all-expenses-paid tropical holiday.  This would be the first of the legendary "Mad trips", which became an annual tradition.

Gaines' elaborate planning became the butt of many jokes during the trips.  Don Martin once remarked that Bill was "sort of like a Sunday school or first-grade teacher.  We almost had to stand in line with no talking allowed."  But his attention to detail was responsible for some of the more memorable events of the trips.  Before leaving New York on the first trip to Haiti, Gaines had checked to see if Mad had any Haitian subscribers; he found that there was only one, and also that the man was about to let his subscription lapse.  Upon arriving at the island, Gaines piled the entire Mad group into rented jeeps and headed for the man's house.  The group greeted the stunned reader at his door, Gaines bestowed on him a gift subscription, and the Madmen all drove off into the sunset.