Planks along a Pirate Ship’s hull?

Hey Ross,

you can use Proportional Editing, but maybe a Lattice iModifier is the better option (needs to be Applied, when ready, of course).

Either way, make sure you have enough geometry.

Quick and dirty 'proof of concept'::

Depending on what you will use your completed model for, you don't need to model individual planks.
You could make the boat shape, from a cube for example, and use loop cuts to add the effect of individual planks.

If you already have the hull and you still want the planks to be individual, you can duplicate the hull and just cut it like a plank and that plank will have the shape of the hull. And just repeat there after.