Vastly more accesible than its predecessor Sunless Seas, Sunless Skies does a good job of on-boarding. The writing is just as delightful as the first game, but tonally it hasn't grabbed me as much. The controller support was a big selling point for me as I'm a couch gamer, but be warned that at the time of writing using a gamepad is a pretty horrible experience and the controller support seems pretty unstabel and prone to breaking. If you enjoyed Sunless Seas you will almost certainly enjoy this game. If you didn't play the first then I highly recomment starting here.
I'm sure we all know DK2 to be a great game but be warned, despite GOG's claims that this has been updated to work with all versions of windows it quite evidently doesn't based on my experience and looking through the forums. I'm on Windows 8.1 and none of GOG's suggested fixes are working for me. Very disappointing. If you can get it to work it's a great game, a classic, but that is a big IF.
