Lately my reading into colonial history has taken me to the 17th century Caribbean basin, and the rise of buccaneers, and later pirates. One striking component, as you read about the life stories of notorious buccaneers and pirates, is how their rise to glory or infamy parallels the murder hobo career of characters from D&D or your favorite retro clone™. They start out as poor fighting men, usually ex-hunters or military, who turn to raiding to earn a better life. Early success wins them a ship, and as their name grows, more and more men flock to their banner and they become capable of launching larger raids - sometimes with multiple ships or small armies of buccaneers, eventually sacking major towns and forts. In the twilight of their career, they take their fortunes and retire to governorships, plantations, or high stations in the military - or they're killed in action. It's a 50-50 proposition.
The issue I see with such a campaign arc in D&D is that it doesn't handle large scale combats very well, and certainly not if characters are just low level participants. I imagine smaller raiding and boarding actions can be handled tactically, using the standard rules, but it would become unwieldy once more than 50 or so combatants per side are engaged.
If you were to go outside of D&D to borrow ideas from a system that handled ship-to-ship combat, chases, boarding actions, and similar aspects of high seas action, what would it be? I also think it beneficial to shift the scale as appropriate; perhaps the distance-based combat ship-to-ship starts abstract, but when the ships reach boarding range, play moves from a strategic scale to a tactical scale and the players resolve the remainder of the combat using standard rules.
I'm not averse to looking at Sci Fi either, I imagine a starship-based game could have similar issues where the combat needs to shift from ship-to-ship combat to personal combat. Not everyone can be the captain, after all. I might be missing some game approaches that handled transitions and troupe play.
Incidentally, following the muse a bit, I've been sketching notes for a short horror scenario in colonial waters that involves a derelict Spanish vessel drifting along the coast. Was it part of one of the famed treasure fleets, lost in a storm, or is something else at play? The adventure hook is being asked to join a merchant's expedition, either out of Jamestown (to the north) or up from the Bahamas, to find and recover the derelict after it was spotted by a vessel just making port; adventurers are needed for the kind of fighting and exploration of which the regular sailors are ill-prepared. Although it's free form, some of the potential encounters involves French pirates, native villages along the coast, and a dark horror from the Mesoamerican hinterland. It's shaping up to be great fun. But it's got me thinking again how an actual saltbox type campaign might be played out.