Baron Raymondo works in the following manner.
1. To spawn a Raymondo, the player must pay off one of the Mysterious Traveler in the taverns. It doesn’t seem to matter which one, so long as he offers to sell you information regarding your family. This information costs 1,000 gold on the middle difficulty setting. Once paid, Raymondo will be generated in the city he mentions, but he probably won’t stay there for long....
2. Once created (there is never more than one Raymondo active at a time), he may stay put, but more likely he’ll begin sailing between cities as quickly as he can. I’ve literally seen him pull into port only to leave a second later. It may even be possible that you can’t catch him in a city, that if he’s holed up in a town, he’s triggered to leave once you come within a minimum distance. I base this speculation on the fact that I’ve spent game years on the opposite side of the map doing things, and Governor’s Daughters keep giving the same location hint for him, but the moment I actually go track him down he starts playing Musical Towns.
3. He only seems to travel between full-fledged cities, never settlements.
4. Once caught (requiring the standard ship battle and a fairly easy swordfight), he gives up a map piece to a lost relative and a flat 3,000 gold in plunder, then vanishes from the game until another one is generated by a Mysterious Traveler.
5. If a family member is found while Raymondo is at large, he disappears, and another one must be generated to start on the next map. According to GameFAQs, Raymondo stops appearing entirely once the last map piece is delivered or the last family member is found.
It can be difficult to track Raymondo down, but it is also entirely possible to blunder into him during his frantic city-jumping. It is usually a good idea to have Raymondo roaming around, even when you’re doing something else, in order to encourage these accidents as the battle is seldom difficult and it’s 2,000 gold profit plus it’s worth loot, a fairly valuable ship (usually selling for 1,800 gold) and possible crew members if you beat him.
Beating Raymondo (up to sixteen times in one game) generates family map pieces. Rescued family members generate a Marquis Montalban who roams the board according to similar (if not identical) rules to Raymondo, a fairly difficult fight who can be defeated for 5,000 gold and a piece of the hideout map. Finding the hideout produces a Vs. Indian land battle and then a high-difficulty swordfight against Montalban. (The first trouble I’ve ever had with the swordfighting in Pirates! has been against him.) Beating Montalban here is worth several fame points (maxing out your Villain score), and 100,000 gold, the largest single award in the game. But perhaps more importantly (according to multiple FAQ sources), any remaining family members will give you Lost City maps when rescued, and Governor’s Daughters will also be a bit more willing to cough one up (especially, perhaps, your wife if you have one). There are four Lost Cities in the game, each worth 50,000 gold and fame points when found. The Lost City quest is the hardest to finish, seeing as how you barely even get those maps without either near-mastery of the dancing minigame or having defeated Montalban. You’re probably already halfway through your pirate’s lifespan by the time you’re able to start tracking them down.
Note that all of these maps are worth fame points themselves. If you find a map’s target before getting all its pieces, you’re spotted free fame for all the fragments you didn’t find. Tracking down Raymondo is the greatest time sink in the game, so it is definitely worthwhile to try to find family members before you have the whole map.
It takes a lot of sailing around to hunt down Raymondo all those times, chase down Montalban, find map pieces, search for family members and that hideout, and look for Lost Cities. So ultimately, it seems that Pirates! is a game about optimizing the sailing routes between places. Sea battles aren’t difficult to win at reasonable difficulty levels, swordfighting isn’t much harder, but sailing against the wind for almost the entire board to get to a Raymondo hiding in Cumana can waste a hell of a lot of game time. Because of this, I’m guessing that, of the available skills at the beginning of the game, the most useful of all is either Medicine (giving you more years to do things) or Navigation (which increases sailing speed and helps in sailing against the wind, allowing you to make the most of the years you have).
As far as using maps goes, the most important fragment is the one that tells you its target’s location in relation to a city, since then you can go to your world map and find the area it’s hiding in, going by the shape of the coastline in the map. Maps usually have at least one aquatic landmark in them which can be seen from your boat, although the landmark may actually be in an inland lake (such as when something is hidden north of Flordia Keys).