Believe it or not, I hauled a 28’ Stamis cuddly cabin with 350 cid Chevy and Volvo out-drive for 350 miles, but Florida is flat. Climbing grades might have been an adventure, but it did much better than I expected. The Tacoma has a little bitty 3.5 liter V-6 but that little sucker cranks out 278 hp and 265 lb/ft of torque. Mine has the 6-speed auto, but a stick probably would have worked better. Johnboy’s is heavier and I’d think the 4wd would put even more strain on things, but it’s a surprisingly peppy little motor for its size. It sho’ ain’t gonna pull like that big ol’ diesel, but I don’t think a smaller boat will be too tough, especially since I don’t think the island has the greatest elevation changes to fight.