Did that truck come from the factory w/a tow package?...Ferm's ZACKLY right about a transmission cooler...add one if you need to...
The route to where the boat is...is it a hilly one or relatively flat?...I-95 that Willy & Rob did to Charleston is fairly flat land...if you got a mountain range to traverse, you might wanna find another way...then there's the question of braking power...you ain't got a favorite uncle w/an F250?...