Company of Heroes aside, generally I prefer to have my World World II strategy filtered through The Flare Path. Better to admire from afar than shame myself by attempting to understand such things first-hand. Victory At Sea has proven surprisingly accessible, however, despite its concerning itself with enormous boats and Winston Churchill soundbytes. It's by no means Assassin's Creed Black Flag with 1940s Destroyers in the Pacific, but it's at least as much about good times as painstakingly-recreated times.
I've only had a quick blast, but while it's got some distracting presentation issues and I'm not sure about it having separate travel and combat modes, but it certainly offers a jolly great boat fight without too much fuss. Weapons take a while to reload (unless you use the speed up time button), but other than that it's pretty much aim and shoot.
There's also an RPG element I've not seen much of yet, which involves optional missions and fleet upgrades. I'm keen to have a fiddle with that stuff if I get the chance.
Apparently it's based on a boardgame of the same name, but the rules have been simplified which is always a risky business.
Victory At Sea has been out on Steam or direct from the devs (UK studio Evil Twin Artworks) for a little while now. Sadly no demo - and this is exactly the sort of game which really could do with one, given that it's $25 and its main shtick is accessibility to the naval-fearful - but here's the requisite trailer for you:
The Imperial Japanese Navy was added as a playable faction a couple of weeks back, joining the US and UK navies. Whether the notable omission there will be added in a later update I don't know.