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What do we do with a drunken sailor? In The Caribbean Sail, that’s entirely up to you. You could let him sleep it off. Maybe you restrict the crew’s rum rations. Or maybe you’re feeling sadistic and you publicly flog him, one lash for each shot. That’s the beauty of The Caribbean Sail; it may look like a watered-down variation of the infamous Oregon Trail, but the implied roleplaying takes this one-developer indie game to another level.

You play a ship’s captain in London, sometime in the mid-1700s. You have a contract to check up on a port in the Caribbean. Along the way, you can join the warring factions of the era or go into business for yourself as a pirate of the Caribbean. You can choose from a number of backgrounds and social classes, each with advantages and disadvantages. If you hate yourself, you can even play as a holy missionary riding a raft made of driftwood and stained sheets. The best a missionary can hope for is a lightning strike to the powder kegs.

caribbean sail open water

This is what you’ll see most of the time, accompanied by an 8-bit sea shanty.

Ocean travel is largely determined by random events. Crew members make mistakes. Your barrel of hardtack is full of rats. You might run aground of a reef. However, Similar to Oregon Trial, The Caribbean Sail is full of minigames. There’s a fishing minigame, a naval battle minigame, and liar’s dice to keep things fresh in between long journeys. Unfortunately, the minigames are very easy. The Liar’s Dice AI isn’t great and the fishing minigame is a reliable source of infinite food because you get your ammunition back so long as you score a hit.

More interesting than either the random sea events or minigames is your relationship to the crew. True to reality, you must keep your sailors happy and healthy. It’s your job to distribute daily rations of saltfish and the occasional mug of grog. Moreover, you need to decide when to discipline your crew for their mistakes and to what extent. If a crew member is particularly sick or hurt, you may have to break out the bone saw and play Surgeon Simulator 1713.

When these individual elements combine, it sets the backdrop for some wonderful roleplaying. This is further reinforced by the “Captain’s Log,” an in-game journal for your thoughts and notes. I couldn’t help myself from writing a journal entry whenever something interesting happened. Moreover, whenever you die, you can leave a message in a bottle for other players to find. It made me feel surprisingly connected to my crew, who were just faceless names and number values. The Caribbean Sail is the most fun I’ve had with implied roleplaying since Dwarf Fortress.

caribbean sail liars dice

There are only two dice left, and the AI bet 2 – 4s…

One place where The Caribbean Sail stumbles is in the trading. Aside from adventure game-style utility items, there are only a handful of useful trading items. What’s more, is that the strategy is always the same. Buy “luxuries” cheap in London or China and sell them in America to double or quadruple your investment. That’s your primary means of making money unless you obsess over Liar’s Dice. It reminds me of Sunless Sea in a way, but The Caribbean Sail only has on trade good and a handful of ports while Sunless Sea’s trading simulator had a wide variety of islands, cultures, and trading goods.

The 8-bit soundtrack greatly elevates both the gameplay and tone. Pick any traditional sea shanty. Got it? Well, there’s a very good chance the developer behind The Caribbean Sail has made it an inventory item. As someone who unironically listens to sea shanties while working, hearing them in this context made me smile ear to ear as I checked every single store to find the ever elusive “Randy Dandy O.”

caribbean sail message in a bottle

Rest in peace, you poor bastard.

The Caribbean Sail is a tale of ups and downs, rising and falling in time with the salty swell. And yet, even as a few waves of missed opportunity crash into the ship, the crew, their songs, and your stories brighten the darkest night. What’s more, even a year and a half after release, the “one nautical enthusiast” behind The Carribean Sail is active on the game’s Discord server and puts out regular content updates, balance changes, and is even working on a “fantasy toggle” which would add sea monsters, ancient treasure, and other mythological elements. If you have any interest in nautical games, sea shanties, or the Oregon Trail, you owe it to yourself to try The Caribbean Sail.


TechRaptor covered The Carribean Sail on PC via Steam with a copy purchased by the reviewer.


Ron Welch

I love dissecting game design, seeing what works and what could be improved. While RPGs, shooters, and strategy games are my favorites, I'll tackle just about anything. I also do voice overs, make an award winning wing sauce, and (formerly) write about post-apocalyptic goodness.



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