
The Caribbean Sail
Name your crew, purchase supplies, sail the world, harpoon fish, plunder your enemies, die horribly, unlock a new Captain and do it all over again!
Still thinking about Bootleg Steamer and its replayable and funny tone? These games make natural next picks for you.
Prohibition made booze illegal, and that is your business plan. Start with homemade hooch in 1920, build stills and speakeasies, work favors and bribe cops, and grow a criminal outfit into the city's money machine before 1933 ends the party. A turn-based tycoon game about supply chains, connections and nerve.
Also in Tycoon · Replayable
Make your name as a whiskey-runner, a politician, or a gangster as you quench thirsts from rural Pennsylvania to the New York City nightlife!
Replayable, Funny, Tense
Manage your own speakeasy hidden from prying eyes during Prohibition. Experiment with recipes, perfect the quality of your spirits, and transform your bar into an elegant, unique venue. Combine craftsmanship, optimization, and decoration to offer your guests an unforgettable experience.
Also in Tycoon · Atmospheric
Sail the 13 colonies as Mr. Law, a merchant with a slightly used ship, buying low and selling high while blockades, battles and your own greed move prices. Dodge patrols, manage crew and taxes, pick a side in the war, and date state-chans who run the shops.
Also in Tycoon · Replayable, Funny, Colorful
Step into the world of bootleg booze in this story-driven, single-player sim! Grow your crops, brew your drinks, bond with eccentric customers, and bottle it all under your own brand. Uncover the truth behind your brother’s arrest, complete quirky missions, and build your underground empire.
Also in Tycoon · Replayable, Atmospheric
Step back in time to the roaring 1930s and immerse yourself in the high-stakes world of bootlegging during America's Prohibition era. Get ready to join John Hamerton, a retired car engineer and mechanic, as he embarks on a daring journey to save his house and pay off his tax debt.
Atmospheric, Tense
You’re the captain of a cursed ship in this crew management roguelite! Command your crew, keep the ship afloat, defeat pirates and deep-sea beasts, and sail as far as it takes to lift the curse.
Replayable, Tense
Name your crew, purchase supplies, sail the world, harpoon fish, plunder your enemies, die horribly, unlock a new Captain and do it all over again!
Replayable, Funny, Colorful
Sail the Caribbean as a pirate or a privateer, fight ship duels, raid towns, court governors' daughters and dig up buried gold. An old-school sandbox where every voyage plays out differently, and one more trip out to sea is always tempting.
Replayable
Race against a 3-year death clock in this economic Roguelite. Sail the Mediterranean, exploit extreme market surges, and amass 500 million gold. Fail the run? Inherit your treasures into the next playthrough and continue the struggle to defy destiny!
Also in Tycoon · Replayable
Drug Dealing RPG roguelite strategy crime saga with choose your own adventure elements. The police and the jackboys aren't your biggest enemy... Time is!
Also in Tycoon · Replayable
Reclaim the Sea is a roguelike strategy game set in a pirate fantasy world. Fight your way through randomly generated maps and text events. Command your pirate crew, upgrade your ship and make tactical decisions to beat the boss and save the world… or die trying.
Replayable, Colorful, Tense

Name your crew, purchase supplies, sail the world, harpoon fish, plunder your enemies, die horribly, unlock a new Captain and do it all over again!

As a Chicago mob boss at the start of Prohibition, you must make tough decisions to manage your crime empire. How many hoods to employ?

Captain a ship in a turn-based pirate roguelike set in 1669.

Sunset Routes is an easy and intriguing roguelite game. You can choose your crew, put them in the cabins, select your destination, and set sail.

Stake your claim on the city of New Shore in this gritty simulation of 1930’s organized crime.

This is a world of oceans, islands and ships. Players will start their own journey from Faro, facing an impermanent ocean and awkward opponents, and…

Captain a ship across an open sea of islands, trade routes and ship-to-ship fights.

Build a drug empire from a filthy hideout to a city-wide operation.

Set sail on your adventure to become the number one merchant in all the world! Trade, fight, or negotiate your way to the top in your own style!

Pirates? Pirates! is a Reigns-inspired pirate survival RPG. You are a pirate captain in charge of your ship and crew on the most dangerous adventure…

To escape the city of Starkham and start your new life, your friend Preston sets up a meeting with the local loanshark, Sweaty Mike.

High and Dry is a swash-buckling strategy rogue like where you race against time to save your soul from Davey Jones!

Sail the 13 colonies as Mr. Law, a merchant with a slightly used ship, buying low and selling high while blockades, battles and your own greed move…

Step into the world of bootleg booze in this story-driven, single-player sim!

Ahoy, matey! How about slicing up some sea beasts and sending a couple of rivals to feed the kraken?

Sail, trade and fight your way across an open pirate sea where every run takes a different course.

Live your medieval trader life! Buy low, sell high and explore the world! Buy ships, build businesses, find or train captains.

Steal cars, run clubs and warehouses, and grow your gang until every district answers to you.

Sail the Seas is a sailing, trading simulator set in 18th century, spanning whole world

Run a shady little shop on a dystopian space station, crafting and trading your way through a rising weekly bill. ---

Lead Captain Cutter's crew through turn-based naval battles and boarding brawls, where every run brings a new map and new ways to win.

Become a Mighty Captain in a Age of sail naval combat game, set in all of the Seven Seas!

Thrilling business tycoon sim where you step into the shoes of a drug dealer in 1980s USA. Your main goal is simple: BUY LOW and SELL HIGH.

A tranquil world becomes ever more corrupt by the day, spoiled by a pirate organization that forcefully impose their brewing monopoly over the lands.

Steal cars, run clubs and warehouses, and grow your gang until every district answers to you.

Sail the 13 colonies as Mr. Law, a merchant with a slightly used ship, buying low and selling high while blockades, battles and your own greed move…

Ahoy, matey! How about slicing up some sea beasts and sending a couple of rivals to feed the kraken?

A pirate city builder where flat land is scarce, so you build up the cliffs: bridges, ziplines and lifts hauling rum and cannonballs between camps.

Steer to aim. In this top-down naval roguelite your broadside is the crosshair: swing it across a pirate's stern for double damage, read the…

Step into the world of bootleg booze in this story-driven, single-player sim!

Sail the Seas is a sailing, trading simulator set in 18th century, spanning whole world

A 17th century Caribbean sandbox where you own your ship and answer to nobody.

Sail, trade and fight your way across an open pirate sea where every run takes a different course.

Live the rise and fall of a gangster in Prohibition-era Chicago.

Manage your own speakeasy hidden from prying eyes during Prohibition.

You are lost in the Bermuda Void, where the ocean is endless and dry land precious.