General
At the beginning you want to get navigation points fast. You should take deliver letter missions and deliver them to the city named in the mission within the time mentioned. For every letter delivered within time you get extra navigation points, so your navigation skill will rise faster. It also has another advantage, for every 3 Navigation levels you can take an additional mission and get even more points. After the first couple of jobs you get the feeling of which jobs are doable. There is a good route in the start area of every nation. It’s important the to do the jobs as fast as possible which means a fast ship (sloops) and sail in a straight line without any detours, cannon fights or fencing. The faster you get the job done the more navigation points you get. After you have finished the job put the money in the bank.
After a while you will have enough navigation to use more/bigger ships, but until navigation level 16 you should use the sloop, because those are the fastest ships in the game and in the beginning running away from trouble is the only way too stay ‘alive’. When you get navigation level 16 (with/or without Mate) you can sail a Barque. In the beginning it’s important to sail with more than one ship, because you can easily lose a ship. The reasons for this could be overnav (taking a ship that gives you more total navigation that you are able to handle), overloading your fleet with goods, cannons/ammo, crew etc. and of course from NPCs or players.
After collecting navigation points and maybe finding a better mate, the beginner should get more ships. To do this there are different possibilities: Buy/build at the shipyard, take a ghostship, ask in nation for someone to give you one or fence one yourself. You may prefer to fence one on your own, because the fence skill increases that way. You have to pay attention to which ships you fence. Go for the nation ships and avoid the pirates, because they are too strong at the beginning. Before you go into fence you should target the enemy ship (press ) and only fence when the right most number is -2 or -3, with -3 as the best (and you have veteran crew). Otherwise you have to shoot at them with shatter ammunition (press ) to reduce the crew of the enemy.
With Navigation 12 or more you could easily go on a world tour (use fast ship like sloops or barques), the advantage in this is that you will get new navigation points from exploring unknown waters (the black) and finding new cities and you get to know the world. If a city is without a fort everybody can enter (press ) and look for specs, refill your wood/cloth, get more crew/food/rum. If a city has a fort your nation and the nation of the city is important, if there is war between the nations or you have negative reputation with the nation, you can’t enter the city. In every city you enter, check for better specialists and if necessary get some jobs, but not those with a time limit or capture jobs. Do this so you can make some money on the world tour. A world map is very useful on this trip.
After you finish the world tour you will have about 30-40 more navigation levels than before, depending on what level you started out with, the earlier you start the tour the more levels you gain. At the beginning it’s not worth the effort to skill for a bigger weapon or fence skill (like 6 or more), because its way easier to get those later when you fight with more crew and cannons.
The Specialist
The deal with the specialist is that at the beginning you don’t have a high enough navigation level (every 2 navigation levels you can take another specialist) to take all required specialists. So you have to decide which specialist you should take. At the start when you often end up on a raft and have no loyal specialists, you get a free +1 mate. When you have a bit of cash in your account, you should get a better mate and a better lookout with a big visible range (highest 990) so that you explore a lot of black when you sail around (and get the big nav bonus). After that you should every time you enter a city search for better specialists. The future choice of specialists depends on your plans. Are you going on world tour, exploring the near surroundings, fence a lot or shoot? What you choose will have a say in which specs you should take, for the world tour you need a good mate with high speed bonus, while the fencer needs a soldier with high moral bonus. At the beginning it’s difficult to get the best specs because you haven’t got the minimum requirement for the specs yet or you just don’t have any luck in finding them. Every city has different kind of specialist that it generates more of, there are cities that have more good cooks or carpenters, another often has good soldiers or cannoneers. In the noob area most specialists are not strong except the carpenter. If you at the beginning find a good carpenter (92-94 %), you should take him because those are the most difficult to find. You will on your journey through the Caribbean, find out where you can get good specialists.
At the beginning you are not able to pick up a lot of specialists but this changes fast as the game progresses, but soon (ca. at navigations level 30) you should have found a lot of good/very good specialists. As soon as you have room for new specialists, he should fill those with carpenters with high speed, and cooks with high morale bonus (a 4.9 per approx. 150 crew). There should later be room for a couple of fishers. The carpenters with high speed stack, so the ship can in one repair turn get more % repaired. Cooks are needed to keep the moral of your crew up. As you soon can sail more and/or bigger ships, the crew number also rises, and this affect the morale, which only can be held high with rum, battle or the right numbers of cooks. The fishers are needed to keep food in stock so the players don’t run out on a long journey.
The beginner should always keep an eye on the bank account, because unloyal specialists leave if you can’t pay their salary. You would also lose the specialists if you end up on raft. When a specialist is loyal depends on the loyalty points (Crew->Specialists->Choose Specialist and watch the bar) the specialists got. You get loyalty points while sailing (10 sea miles = 1 loyalty point) or if you just stay in the water a certain distance from a port (30 secs = 1 loyalty point). If you ends up on a raft and the specialists leave, you can go, as fast as possible, to the nearest town and get some of the specialists back from the pub.
The Choice of Ship
The ship class that meets the max requirement for your current navigation level gives you more navigation points per sailed sea mile then if you sailed with another class. And you will learn the abilities of the different classes. I wouldn’t advise the player to sail all ship classes, because some of them are really slow, and the extra points you get for sailing them are equalized by the speed of faster ships. I would advise to leave the pinnace behind at the beginning and sail sloop until you can sail a Barque. Later I would skip the Merchant, because it's really slow. The ship classes that can be sailed depends on the your navigation level.
If you're going to trade you should use Merchants or Spanish Galleons. If you want to do capture jobs, then you need a lot of crew and/or cannons. In both cases the player should calculate navigation costs so he will get the highest number of cannon/crew/freight room. This is for jobs and not player vs. player, more about that later.