Overview: Players play as one of nine clans of Caledonia, expanding over land and sea to establish production chains, fulfill contracts, and become the most successful clan of them all. Gameplay takes place over a setup phase followed by five rounds.
Setup. After turn order has been randomly established, each player chooses a clan in reverse turn order. There is always one more clan available than the number of players in the game. Then, in turn order, each player takes turns putting down two workers (miners or woodcutters) on the map. These serve as starting points for expansion in future rounds; the two workers can be placed anywhere on the map, but subsequent placement in future rounds must be connected to previous units.
Rounds. In turn order, players either (i) place units on the board, (ii) take a contract from the contract board, (iii) buy or sell goods, (iv) buy merchants, shipping upgrades, or worker upgrades, or (v) pass. If a player has access to a port (located at the corners of the map), the player may use the port as a bonus action before the main turn. Multiple ports can be used in the same turn. Each port may only be used once.
Placing units. The total cost of each unit is the sum of a fixed unit cost and a variable land cost from $1-6. Units on land must be adjacent to each other; units next to water may extend their placement range by a number of water tiles less than or equal to their number of shipping upgrades. The first shipping upgrade allows players to cross streams (water along the edge of tiles), the second allows players to cross up to one water tile, and so on. There are five possible shipping upgrades, each costing $4.
Woodcutter - costs $6 - produces $4 (+$2*) each round
Miner - costs $10 - produces $6 (+$2*) each round
Sheep - costs $8 - produces 1 Wool each round
Cow - costs $9 - produces 1 Milk each round
Cheese - costs $8 - produces 1 Cheese from 1 Milk each round
Grain - costs $18 - produces 2 Wheat each round
Bread - costs $8 - produces 1 Bread from 1 Wheat each round
Beer - costs $10 - produces 1 Beer from 1 Wheat each round
The woodcutter and miner can be upgraded to produce an extra $2 each round (see 'Worker upgrades', below).
-- Placing units that neighbor other players' units over land, not crossing any water will trigger a neighborhood bonus, allowing the player to purchase up to three goods produced by neighboring units for a $2 (raw goods: wool, milk, grain) or $3 (processed goods: cheese, bread, beer) discount over the market price. This is a bonus action that takes place after the main turn. Each purchase requires one merchant. A neighborhood bonus may be triggered for multiple neighboring units in the same turn.
-- Placing four production facilities of the same kind triggers a contract bonus, as depicted on the bottom of the player board. If the player's contract slot is empty, the player may choose from one of three random contracts drawn separately from those of the main contract board. The player must still pay the round cost for taking a contract.
Taking contracts. Players may take contracts from the contract board for a certain cost depending on the round---the costs for each round are, respectively, -$5, $0, $5, $10, and $15. Yes, you get $5 for taking a contract in the first round. Players may have at most one unfulfilled contract at once.
Buying or selling goods. Every good bought or sold requires the use of one merchant, which is then locked for the round. Players start out with two merchants, and can unlock up to five more for $4 each. Buying or selling goods respectively raises or lowers the position of the good marker on the market board by a number of steps equal to the number of goods bought or sold. This makes it more cost-effective to buy in bulk in one go. In a single round, a player cannot buy and sell the same good. The same rules apply to the neighborhood bonus (see above, 'Placing units that neighbor other players' units').
Buying merchants, shipping upgrades, or worker upgrades. The purpose of each upgrade has been detailed in the sections above. Merchants cost $4 and allow for more buying and selling from the market. Shipping upgrades extends the reach of tiles adjacent to water. Worker upgrades cost $10 and increase the profit from each worker by $2 per round.
Passing. Once the player cannot or does not want to keep performing actions, the player can pass, stopping them from performing any more actions this round. The order in which players pass determine their turn order for next round; passing early also gives a slight monetary bonus for next round. In all cases, passing gives at least $10.
After all players have passed, the production phase is triggered. Players decide what combinations of goods to produce with the units they have, end-of-round scoring takes place, and the next round begins.
Scoring. The main contributor to points are, in descending order, contracts (hops, sugar cane, tobacco, cotton), glory (end-of-round scoring), longest settlement and most contracts achievements, and goods (raw, processed, and money).
Contracts. Each fulfilled contract gives up to three benefits---0-4 of an import (sugar cane, tobacco, and cotton; the rarest import is worth five points at the end of the game, the next rarest worth four, and the most common worth three), 0-9 hops (each worth one point), $3, $5, $10, or $15, an expansion bonus allowing you to expand once without paying the land cost, or 1-2 free upgrades (worker upgrades are reduced from $10 to $5 instead).
Glory. Victory points are obtained for satisfying randomly drawn objectives after each round, as depicted on the top of the main board.
Longest settlement. Each settlement is a group of units connected by land. The player with the most (then second-most and third-most) settlements gets the points listed at the top of the main board.
Most contracts. The player who has fulfilled the most (then second-most) contracts gets the points listed at the top of the main board.
Goods. Raw goods are worth one point each and processed goods two. $10 is worth one point.