Each player uses a separate small board with spaces for city buildings, plantations, and resources. Three ships, a trading house, and a supply of resources and doubloons are shared between the players.

The resource cycle of the game is that players grow crops which they exchange for points or money. The money can then be used to buy buildings, which allow players to produce more crops or give them other abilities. Buildings and plantations do not work unless they are manned by colonists.

The game has a three-layered turn structure: during each round, every player chooses a role (Captain, Mayor, etc.), and whenever a role is chosen, every player can take the action appropriate to that role (though the player who chose it gets a small additional privilege). The right to start a round, to choose roles within a round, and to take the action for the chosen role, all pass to the left.

Players get victory points for owning buildings, for shipping goods, and for manned "large buildings." Each player's accumulated shipping chips are kept face down and come in denominations of one or five. This prevents other players from being able to determine the exact score of another player. Goods and doubloons are placed in clear view of other players and the totals of each can always be requested by a player. As the game enters its later stages, the unknown quantity of shipping tokens and its denominations require players to consider their options before choosing a role that can end the game.

The game ends if:

1. Mayor is selected and there are not enough colonists to refill the colonist ship
2. Captain is selected and the last VP chip is given to a player. (Additional chips are to be used once the supply is exhausted)
3. Builder is selected and at least one player has built their 12th city space.

In each case, players finish the current round before the game ends. The winner is the player with the most victory points. In the event of a tie, the player with the most goods plus money is given the tie-breaker. If a tie still exists between players, those players tie.

The game consists out of many rounds.
One round consists out of every player taking a role and finishing the action.
The "Governor" is a random person in the beginning; then it gets passed on to the next player after each round ends. The Governor starts the round by choosing a role. After he chooses the role, he starts with doing the role action (and privilege), then each player does the action. Then the next player in turn chooses a role. That continues until every player has chosen a role. Then the next round starts (with the governor being passed on).

There are buildings and goods that help you to get victory points.

Goods can only be produced if you possess the respective manned plantations and buildings. Buildings also need to be manned to give you the bonus.

Each player has 12 building spots and 12 plantation spots free. Whenever he buys a building or gets a plantation, he needs to occupy a spot for it. Buildings and plantations can NOT be removed after acquired.

There are 7 different roles. Each player chooses one of them in every round. Depending on the role, every player does the action of that role, but the person who chose that role will gain a privilege.
If a role has already been taken in the current round, you cannot take it anymore.
At the end of each round, each of the unused roles (3) gets an extra doubloon on it (means next time you choose it you get a doubloon) to make it more attractive to the player.
The Prospector role is not available in 3 player games. In 5 player games, it is available twice.

Settler: Each player takes a plantation from the open ones.
Privilege: The settler can take a quarry instead of a plantation.

Mayor: Each player receives colonists and can rearrange them on their field.
Privilege: The mayor gets one extra colonist.

Builder: Each player is allowed to (but doesn't have to) buy a building.
Privilege: The builder pays a doubloon less for the building.

Craftsman: Each player produces goods depending on the manned plantations they have.
Privilege: The craftsman can produce one additional good (from the ones he produced).

Trader: Each player is allowed to sell one of their goods to the trading house and earns money.
Privilege: The trader receives an extra doubloon for selling a good.

Captain: Each player has to ship their goods onto the transport ships. (More detailed explanation later.)
Privilege: The captain receives an extra victory point (minimum of 1 shipment).

Prospector: No action for the other players.
Privilege: The prospector gains a doubloon.

Settler Phase: There should be ({amount of players}+1) open plantations to pick from. Those plantations are of a random goods type.
The settler himself starts with picking a plantation. He can take a quarry instead of a plantation. Also, anybody with a manned constable hut (see Buildings) can take a quarry instead. At the end of the Settler Phase, the left open plantations are removed and new open plantations are opened.

Mayor Phase: There's a colonist ship. The minimum amount of colonists on that ship equals the amount of players. (The game also starts with {player amount} colonists on the ship.)
Each player (cycle) gets one colonist from the ship until there are no more left. Then the mayor gets an extra colonist. After that, everybody rearranges the colonists on his playfield as he sees fit.
Then the colonist ship is refilled: It contains as many colonists as many FREE BUILDING SPACES there are. But the minimum amount is the amount of players, as we know.

Builder Phase: The builder starts with buying a building. He of course requires the amount of doubloons of how much the building costs.
The builder pays a doubloon less for the building (0 is allowed, while a negative number does NOT get you more doubloons), additionally to the manned quarries he possesses (means for each manned quarry you pay a doubloon less (building level restriction, check buildings)). Then each player buys himself a building (max 1 building per Builder Phase, and you're not forced to buy any although it is recommended).
NOTE: Level 4 Buildings require TWO building spaces.

Craftsman Phase: Each player receives goods respective to their manned plantations and buildings. They gain one good for each respective plantation and respective building they have manned (except for corn, which only needs a manned plantation). (A production building with more colonist space needs one manned plantation for each space to get those goods!) The craftsman himself can choose to get an extra good of any of the good type he produces.
There's only a limited amount of each good type though.
(If you possess a factory and produce 2 or more types of goods, you'd get doubloons now.)

Trader Phase: There's a rule: There are only 4 good spots available. The trading house does NOT accept two of the same goods, so if you want to sell coffee but there's already coffee in it, you cannot sell it (except you possess an office).
Each player can only sell ONE good at max. They are also allowed to sell corn while not gaining anything, possibly to prevent a future player to make money from it.
The trader gains an extra doubloon for anything he sells.
When all the 4 good spots are occupied, the Trader Phase is over and the trading house is emptied for future trades.

Captain Phase: This is by far the most complicated phase. The Captain Phase is the main phase to gain victory points.
Some rules apply:

1) There are 3 transport ships. Each ship has a limited amount of good spaces.
2) Each transport ship only takes one TYPE of goods. So if there's one god of corn on it, you cannot load indigo on it.
3) Each transport ship does NOT take a type of good which is already present on another ship.

The captain starts with getting a victory point (as privilege, condition is he ships something). You HAVE TO ship goods if possible. If you have more types of goods stored, you can choose which one to ship first. If the transport ships are all empty, you can also choose which ship to load the goods on (the different capacity amount plays a role here, you should try to prevent the others from shipping...).
However, if you ship a type of good, you have to ship ALL of them (aka if you have 2 indigo, you cannot only load 1 indigo onto a ship. Only exception is if there's a ship loaded with indigo with only one space left).
Once you loaded ONE type of goods onto a ship, it's the next player's turn with shipping. After the last player it's the captain's turn again. The cycle goes on until nobody is able to ship any goods anymore.
You gain 1 victory point for each good you ship.

At the end of the Captain Phase: Every FULL transport ship is emptied. Also, all the remaining goods of each player decays except for one. That means each player can keep a max of ONE good stored.
Having a manned warehouse could prevent this.

There are 5 different types of goods and their respective plantations.
Corn: The most common good. Corn is worth 0 doubloons in the trading house, but you don't need an extra building to produce corn.
Indigo: Indigo is worth 1 doubloon in the trading house. You need an extra building to produce indigo.
Sugar: Sugar is worth 2 doubloons in the trading house. You need an extra building to produce sugar.
Tobacco: Tobacco is worth 3 doubloons in the trading house. You need an extra building to produce tobacco.
Coffee: Coffee is worth 5 doubloons in the trading house. You need an extra building to produce coffee.

Quarry: You can't produce goods with a quarry, but for each manned quarry you possess you pay a doubloon less for each future building you buy. There are always 8 quarries available regardless of player number.

Of course, on first sight it seems to be better to produce expensive goods, but the downside is: The buildings needed to produce them cost a lot more.
Remember that each good, regardless of type, is always worth 1 victory point in the Captain Phase.

The level indicates how many quarries you can max use for these buildings - and how many victory points you get for this building (even if they are not manned, so if you buy a building you get those victory points in any case).
The number in brackets show the doubloon cost.
There are 2 instances available of every building (except for plantation buildings, of which there are 4 for each indigo and sugar building, 3 for tobacco and coffee, and level 4 buildings; 1 of each).
You can NOT have two identical buildings. However, it is possible to fe. have a small indigo plant and a normal size one (as they're actually different buildings).
Each non-production building has 1 free colonist space (aka only 1 colonist needed to man this building).

Level 1 Buildings:
Small Indigo Plant (1) - Needed to produce indigo. Can hold 1 colonist.
Small Sugar Mill (2) - Needed to produce sugar. Can hold 1 colonist.
Small Market (1) - You gain an extra doubloon when trading a good.
Hacienda (2) - Additionally to a plantation you can choose in the Settler Phase, you get a random plantation.
Constable Hut (2) - In the Settler Phase you are allowed to take a quarry instead of an open plantation.
Small Warehouse (3) - At the end of the Captain Phase you can store one TYPE of a good additionally to the one good.

Level 2 Buildings:
Indigo Plant (3) - Needed to produce indigo. Can hold 3 colonists.
Sugar Mill (4) - Needed to produce sugar. Can hold 3 colonists.
Hospice (4) - Whenever you get a plantation or quarry, you immediately get a colonist onto it.
Office (5) - You can sell goods of the same type already available in the trading house.
Large Market (5) - You gain 2 extra doubloons when trading a good (additionally to Small Market, and vice versa).
Large Warehouse (6) - At the end of the Captain Phase you can store TWO TYPES of a good (additionally to the Small Warehouse, and vice versa) additionally to the one good.

Level 3 Buildings:
Tobacco Storage (5) - Needed to produce tobacco. Can hold 3 colonists.
Coffee Roaster (6) - Needed to produce coffee. Can hold 2 colonists.
Factory (7) - In the Craftsman Phase you gain extra doubloons for producing different types of goods. 0 for 1 type, 1 for 2 types, 2 for 3 types, 3 for 4 types and 5 for 5 types.
University (8) - Whenever you buy a building, you immediately get a colonist onto it.
Harbour (8) - You gain an extra victory point for each load of goods you load onto a transport ship.
Wharf (9) - In the Captain Phase you can load one type of goods (no amount limit) onto a transport ship that belongs to you alone.

Level 4 Buildings (elite buildings): require two building spaces; only 1 instance of each
Guild Hall (10) - You gain an extra victory point for each small production house you possess and two extra victory points for each normal production house.
Residence (10) - You gain victory points depending on the amount of plantations you possess. <10: 4pts, 10: 5pts, 11: 6pts, 12: 7pts
Fortress (10) - You gain an extra victory point for every 3 colonists (rounded down).
Customs House (10) - You gain an extra victory point for every 4 victory points you've gained through shipping goods in the Captain Phase.
City Hall (10) - You gain an extra victory point for each non-production building you possess (includes the city hall itself).