Not sure if anyone has done it, but here are my thoughts. A 28ft deck boat is heavy. Heavy boats need a lot of torque. The 377 w/ Whipple would make a lot of torque when it is on boost, which means the motor would be in boost mode pretty much all the time when cruising. I'm not really sure if it would be the right motor combo for a boat of that size.
Darrell.
Agreed. The 8.1 would make a little less torque, BUT, it would do it normally aspirated. If you were going to try a boosted small block, you would be wise to move toward an LS-based engine. Much stronger rotating assembly without actually building a blower motor. Plus, the weight savings of aluminum heads.
However, I will say that years ago, I put a Whipple on a '95 K2500 ext cab LONG bed pickup. It was the 210hp TBI pre-vortec motor. The motor was a fresh GM crate replacement ($1290!). With a TurboCity enlarged throttle body, a pair of matched injectors, Thorley headers, high-flow cat, and Edelbrock cat-back system the truck ran like a scalded dog. Being 4X4, long bed ext cab and 3/4 ton, the engine was already working quite a bit. I pulled trailers from time to time with it and my dad ran the PISS out of it. He is a "90 or nothing" type-A driver, so that thing was in boost ALL the time. That truck is still going with 85,000 miles. Actually, it is out at my sister's place in Lander, Wyoming with a snow plow attached to the front!
So, if the BASE model GM long block can handle that abuse with 7lbs of non-intercooled boost; I would imagine the 377 would not have too much trouble. Still, constantly pushing a large deck boat around in Havasu heat is no small task.