Tips madeira

Worker Placement

You will need at least one worker in Regions 2 and 3 most of the time, as the building actions here are vital to winning. And you will of course also need a worker in the forest. Ideally you want one worker in every region, so that all character, harvest and building actions can be effectively triggered, but Region 1 is less important, given that it has only one building to activate, unless your strategy depends heavily on workers in the colonies (in which case, move them there as soon as possible to maximize the number of turns they will produce).

Region 2:

Moinho: If you have 3 workers in this region you get 5 bread, just before you need to feed your workers.

Capitania: The main way to move workers into the city. If you have 3 workers in the region over 5 turns you can earn an easy 15 points, also (3 points bonus x 5 turns).

Region 3:

Casa da Coroa: Important once you have accumulated guild favours.

Fortaleza: Places one or two workers in the City Watch: this accomplishes 3 things simultaneously so is the most powerful spot on the board (discards 3 or 6 pirates, gives you the potential to earn 4 points or block someone else from earning 4 points in the Honor phase, and sets you up next turn to use pirate dice for extra actions).

Getting and Losing Pirates

Try to avoid having any pirates at game end: in a 2-player game in particular, the 8- or 16-point swing may cost you the game. To play optimally, however, you frequently need to take pirates in order to conserve money, bread or wood, then discard them later. That said, try not to leave yourself with more than 6 pirates at the end of a round.

The main way of discarding pirates is placing workers in the City Watch, via the Fortaleza building action or other means (Scout, the 3rd passing favour, the King's favour). All of these actions will discard 3 pirates (or 6 if you activate Fortaleza's stronger ability). And when you acquire pirates from not paying for building actions, on average you will receive 3 (1 + the result of rolling one die). Therefore, as you approach the endgame, make sure you have an even multiple of 3 pirates.

(Constable allows you to discard half your pirates; it is the only exception to the rule of 3.)

If you have a worker in Region 3, putting a guild die on Fortaleza means you can skip paying for earlier building actions, and then discard the resulting pirates at Fortaleza. This is a good way to conserve money if there is a building action you don't wish to use.

Bread

Never start a round with no bread, as you will need it to modify dice. It is usually preferable to take a few pirates and hang on to a little bread.

The Windmill

Do not neglect to use it to trade goods, gain bread, etc., if this allows you to accomplish an optimal move. Whenever you have a chance, especially early in the game, move up the windmill to save on bread later. (The Miller guild favour is especially useful for this.)

Passing

More actions is not necessarily better: try to pass early, once you've completed all actions you absolutely have to do, and grab a spot as high up as possible. Consider taking the 2 reals to guarantee first pick of dice, favour, and guild to unflip if you do not need the actions lower on the passing column.

Crown Requests

When selecting crown requests, consider whether they work well together, what round you will fulfill them in, and what requests will be left unclaimed for future rounds.

It is vital to avoid getting stuck with multiple copies of the same request in Round 5, as the 2nd copy will score little or nothing.

Urbanization (city workers) is the most useful request, in Round 1 especially, as you are guaranteed to score some points from it with no effort, and scoring 12 or 15 points is relatively easy against unwary opponents.

Wealth of the Nations (money) request is poor in Rounds 1 and 3, but better in Round 5; money is too useful before then to waste on it. At game end it effectively scores only a maximum 12 points (as 15 coins would be worth 3 VP at game end).

Influence of the Guilds is least valuable in Round 1, but can yield 15 or 20 points in Rounds 3 and 5, the highest potential return on a single request.

Market Routes and Expeditions both score up to 18 VPs, but avoid having to fulfill them simultaneously, especially in Round 3, as the upkeep in wood/money on 6 ships is high, and ships cannot be sent Home.

It is helpful to have complementary requests in hand: Market Routes + Wealth of the Nations (trade routes get you money); Influence of the Guilds + Urbanization (claiming Guild favours clears space for urbanization).