Eras

There are 5 eras to choose from in Sid Meier's Pirates. When you create a new character, you choose which era to start in (except if you are on apprentice difficulty). On apprentice, you are locked on 1660-The Buccaneer Heroes. That is the easiest era so beginners choosing apprentice difficulty will find it easier. other eras have either less cities and shipping OR more military activity and anti-piratical activities. Your Starting Ship depends on your chosen nation and era.

Pirates (1987)
This game plays the same era wise as the (2004), but with another era - 1560, in which all towns are Spanish, except for the English-controlled Nassau and Eleuthera and the French-controlled St. Augustine and Florida Keys.

1600 - Merchants and Smugglers

 * Overall Era Difficulty Level: Very Difficult
 * Era Summary: Little shipping and not as many cities as future eras. Caribbean predominantly Spanish. More for experienced players looking for a challenge.
 * Dutch:
 * Ship: Fluyt
 * Ship Usefulness: Extremely Poor
 * Cities: St. Martin
 * Difficulty Level: Extremely Difficult
 * Summary: With only one city, and a poor starting ship, the Dutch are a difficult choice in 1600. St. Martin is not the best situated of cities, but it can be used. A choice for more experienced players, as they are probably the hardest nation to start with in 1600.
 * English:
 * Ship: Merchantman
 * Ship Usefulness: Poor
 * Cities: Grand Bahama, Eleuthera, Nevis
 * Difficulty Level: Average
 * Summary: This is one of the few eras in which the English are not the easiest choice. They have a poor starting ship, and some of the best cities (Port Royale and Barbados) have not been constructed. An intermediate player would likely be challenged with the English above Journeyman difficulty.
 * French:
 * Ship: Sloop
 * Ship Usefulness: Excellent
 * Cities: Tortuga, Petit-Goave, Florida Keys, Port-de-Paix
 * Difficulty Level: Easy
 * Summary: The French are probably the best nation in 1600. They start off with the preferred choice of ship for most pirates and have some of their good cities already built. This is the easiest choice in 1600 for relatively inexperienced players.
 * Spanish
 * Ship: Pinnace
 * Ship Usefulness: Depends on Player - Good -- Excellent
 * Cities: Most Useful: Havana, St. Augustine, Santo Domingo, Rio de la Hacha, Santiago (Many More 10+)
 * Difficulty Level: Depends on Player - Extremely Difficult -- Difficult
 * Summary: While the Spanish start off with an excellent ship (In the right hands), they have so many cities that almost all of the shipping is Spanish. Promotions are therefore hard to come by. Easier than only the Dutch in 1600.

1620 - The New Colonists

 * Overall Era Difficulty Level: Depends on Player: Average -- Good
 * Era Summary: More cities than in 1600, as well as more varied shipping, and more of it!
 * Dutch:
 * Ship: Brig
 * Ship Usefulness: Depends on Player: Average -- Excellent
 * Cities: St. Martin, Curacao
 * Difficulty Level: Difficult
 * Summary: The Dutch now have a much better ship, the Brig in 1620 to start you off. Curacao is a decent base to attack the Spanish Main, and is much better than just St. Martin. While still difficult, they probably have the best starting ship of 1620.
 * English:
 * Ship: Brigantine
 * Ship Usefulness: Depends on Player: Poor -- Excellent
 * Cities: Grand Bahama, Eleuthera, Nevis, Barbados
 * Difficulty Level: Easy
 * Summary: With a decent starting ship, and Barbados as a base to harass the Spanish, the English are much better nation to choose than they were in 1600. The easiest nation in this era.
 * French:
 * Ship: Barque
 * Ship Usefulness: Depends on Player: Extremely Poor -- Poor
 * Cities: Petit-Goave, Tortuga, Florida Keys, Port-de-Paix, Martinique
 * Difficulty Level: Average
 * Summary: The French have gone backwards with their starting ship, from an excellent pirating sloop, to an ungainly and cumbersome barque.
 * Spanish:
 * Ship: Pinnace
 * Ship Usefulness: Depends on Player - Good -- Excellent
 * Cities: Most Useful: Havana, St. Augustine, Santo Domingo, Rio de la Hacha, Santiago (Many More 10+)
 * Difficulty Level: Depends on Player - Extremely Difficult -- Average
 * Summary: While the Spanish start off with an excellent ship (In the right hands), they have so many cities that most of the shipping is Spanish. Promotions are therefore hard to come by. Hardest nation in 1620.

1640 - War for Profit
One of player's favourite eras, with a large, rich Spain and lots of warfare. Unlike many of the other eras, all the starting ships can be used effectively. Choice of nation depends heavily on which nation's ports are most usefully located. War is very common with Spain, who is almost always at war with someone, and frequent wars between the French and English or Dutch for those who choose to take advantage. Pirates use Brig and Sloop classes while Spain frequently uses Royal Sloops as pirate hunters, for those who prefer those ships to the other options.
 * Dutch
 * Ship: Brigantine
 * Ship Usefulness: Poor to Very Good
 * Cities: St Maarten, St Eustasius, Curacao
 * Difficulty level: Easy
 * Summary: Curacao stars off rather poor, and requires some attention if you wish to use it as a base to sell all the cargo that's easy to capture off the Spanish Main. The West Indies tend to have a high concentration of prosperous and wealthy ports, but they are far up wind from the rich Spanish ports.  It's advised to maintain good relations with the French to raid Mexico and Cuba.


 * English
 * Ship: Sloop
 * Ship Usefulness: Good to Excellent
 * Cities: Grand Bahama, Eleuthera, Nevis, Barbados
 * Difficulty: Easy
 * Summary: Barbados is close enough to the Spanish Main. Plenty of wealth in the Leeward islands to buy very large cargo.  Having good relations with the Dutch simplifies raids on the Spanish Main. While not necessary, England in this era benefits most from keeping relations with two nations.


 * French
 * Ship: Pinnace
 * Ship Usefulness: Average to Excellent
 * Cities: Petit-Goave, Tortuga, Florida Keys, Port-de-Paix, Martinique
 * Difficulty: Easy
 * Summary: A very nice spread of ports, especially for ships that can use beam points of the wind effectively. The wealth of Cuba, Hispaniola, and San Juan offer enough to easily become a French Duke.   While France is best positioned to raid Mexico, it can be a long sail home with unfavorable winds.  If one seeks wealth on the Spanish Main, befriending the Dutch or selecting a ship/fleet that  can easily sail beam will make it easy.


 * Spanish
 * Ship: Mail Runner
 * Ship Usefulness: Good to Excellent
 * Key Cities: Havana, St. Augustine, Santo Domingo, Cartenga, Santiago, Campeche (many, many others).
 * Difficulty: Average to Easy
 * Summary: One of the easiest ways to get a mail runner (the largest Pinnace class ship). While the other nations have a few rich ports, they do spawn enough shipping traffic to support a small pirate band and sales to Spain's rich ports is very easy, Spain's wealth and lack of defense are very tempting.  One of the best eras to play turncoat, if one doesn't mind losing access to their ports (or can manage relations with Spain, which isn't terribly difficult either tactically using Jesuits or settlement missions during peacetime, capture of wanted criminals, and occasional pirate hunts).  Good relations with Spain simplifies the main quest considerably.

1660 - The Buccaneer Heroes
The default and easiest era. There are many ships and cities to attack and raid, and not as many pirate hunters as in 1680. There is a good balance, although Spain is still predominant. If Apprentice level is chosen, this is the era you will be forced to start on. The Dutch now have Curacao, St. Eustatius, and St. Martin. This gives them a decent balance on the Eastern Caribbean, especially Curacao, from which it is easy to raid the southern Spanish ports. However, they still don't have ports in the West, so it is recommended that you keep on good terms with another nation in order to have somewhere to dock. The French once again have the ports in Haiti (Tortuga, Petit-Goave, Port-de-paix), the Florida Keys, and a few ports near the Dutch on the Eastern side of the map. This gives them a pretty good spread across the map, although once again, you will need somewhere to dock if you head west. The English now have Port Royale, which is an excellent port as you can raid pretty much anywhere in a decent range and is the farthest west port which isn't Spanish and that hasn't been changed nations by the player. Also, the English have their cities in the Bahamas and Barbados. The only area which you may have trouble with is the South-West corner of the map, Rio de la Hacha, etc., because nobody has ports there except the Spanish. I would recommend just docking at a nearby Pirate Stronghold rather than try and rebalance the whole map in this era. It's easy to do on say Apprentice, where I've conquered the entire map for the English, but extremely difficult on Swashbuckler to Rogue difficulty levels. If you need to, take maybe 1, or max 2 ports for your own side, in order to still have vessels to raid, plunder, and prey on. Finally, the Spanish are still everywhere, but at least there's some other ports to go to. If you choose Spain, I would recommend heading to St. Augustine, Puerto Rico, or Cuba so that the shipping isn't just Spanish.
 * Dutch
 * Ship: Sloop
 * Ship Usefulness: Good to Excellent
 * Cities: St. Martin, St. Eustatius, Curacao
 * Difficulty: Difficult - Easy
 * Summary: The Dutch can still use Curacao as a major and valuable base to attack the Spanish Main and the plentiful shipping. The sloop is the default choice for many pirates, but the Dutch lack any bases in the West, so keeping on good terms with the French is normally a good choice.
 * English
 * Ship: Sloop
 * Ship Usefulness: Good to Excellent
 * Cities:
 * Difficulty:
 * Summary:
 * French
 * Ship: Sloop
 * Ship Usefulness: Good to Excellent
 * Cities:
 * Difficulty:
 * Summary:
 * Spanish
 * Ship: Sloop
 * Ship Usefulness: Good to Excellent
 * Cities:
 * Difficulty:
 * Summary:

1680 - The Pirates Sunset
Dutch are small, Spanish have more territory and most land is split between France and England.