The Caribbean Sail is a rogue-like that is a bit different. You play a Captain who takes possession of his first ship and crew. There are two skeleton stories, one more grounded in reality, the other more on the realm of fantasy, both involving pirates.
One of the main aspects of the game has to be its presentation. Retro-looking, with strong white on black features and great use of colour, it strikes a note between DOS and late Apple II games. It’s clearly inspired on some classics. Obviously Uncharted Waters and Sid Meier’s Pirates, but also The Oregon Trail.
You are then tasked to explore the few ports of the world, taking merchandise and attacking or being attacked, at the same time trying to keep alive at sea over hunger, disease, mutiny or just plain cruel luck.
For its retro presentation the game is surprisingly deep, with a few subsystems like fishing, keel sounding, ship upgrading, character upgrading, a reputation system, a “Mexican” standoff, among others. By themselves the systems are simple, but as they interplay, things get interesting. As in any rogue, luck and random events has a lot to do with the challenge. How you deal with them and how well you've developed your game will play a lot into success.
Unfortunately it also commits the usual sin of rogue-like game design. Playing more is as rewarding as playing better. This means that the longer you play the less challenging it gets as you progressively unlock better ships and character backstories which have better skills or deeper starting funds. Thus, there is no scaling of the challenge, as what was unfathomable at first becomes trivial later. There is a long list of upgrades but, in the end, they do not impact gameplay significantly. The challenge then ends up falling on luck, as a bad spell can have devastating consequences - in the standard mode death will erase your save (keeping of course everything you’ve unlocked for subsequent runs).
You can take it not for more than what it is. Sooner or later you’ll realise you’re just playing with chance algorithms, random events get repetitive and upgrading for the sake of upgrading will feel like ultimately a waste of time.
Yet, on the other hand, the game is perfect for what it is. The setting is fresh and the presentation inviting. This is a small, ambitious game that provides quite a bit of play within and, as you explore the world and deal with tough, split-second decisions to try and brave through just those few more nautical miles and into harbour, there is that spur to keep your save going, try for one more run from Belém to Shanghai if your ship will take it.
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