You approach the old sailor and buy him the rum he asked for, and he begins to tell his tale...
"Listen close lad! And I'll tell ye a tall tale of high adventure and salty sea men!..."

This guide contains everything you need to know, and some of the things you didn't, about how to live a life of adventure and drunken debauchery on the high seas of the olde worlde. Batten the hatches, hoist the main-brace, pickle the yard-arm and oil your peg leg for a rip roaring whirlwind adventure of plunder and pillage, of wenches, ale, and even more wenches and ale. YARR!

Honestly, the best ship in the game is probably the starting Corsair. It's speed and manoeuvrability are not to be underestimated. Clever positioning can keep you in range of only one enemy ship at a time, so as not to be overwhelmed. You can keep you self on the rear of a ship with no rear guns, or keep to the rear or front of a ship on which you have destroyed the rear of front guns respectively, keeping you and your painstakingly levelled up crew out of harms way. The archers on the corsair work way better than the volley guns on the Imperial Wolf ship. The reason for this is that when you are taking on wyverns you will want to sail away from the wind, gaining maximum speed, so that the squigs fall behind your ship rather than on it (orcs can't lead their targets). Not only is it better to have a fast and manoeuvrable ship like the corsair to do this, (especially if the wind changes direction suddenly) the volley gun on the wolf ship is positioned so that when you do this, it just shoots your own ship. This does no damage to you but it does block the shots to the wyvern. In fact it has such a bad arc of fire that this will be a problem with any flyer as it circles your ship. The cheaper Imperial ships have a better arc for their volley gun, but only have front facing weaponry, and cannot "tack" close to the wind (google it), so unless you want to be constantly micro-managing you crew between oars and rigging every 5 seconds, to maximise ship speed and turn rate at any given time.... yea just stick with the Corsair.

At some point you will notice that your crews skills can be upgraded. You should do this. But which ones?

Max skill lvl is III. Even at this level you will need at least 3 crew in each of Repair, Cannons, and Rigging to reach max efficiency. With each of the single role crew slots filled (lookout, cook, quartermaster, cooper, surgeon) that will leave you with only one marine (assuming your using a 15 crew ship, which most ships are, including the starting independent ship, the Corsair.

Once you have gotten your crew the relevant skills to lvl III (rigging for the riggers, canoneering the the canoneers etc.) best bet is to give them toughness to keep them alive.

When you click the "lvl up" button you may not like the options available. This is fine. Just press esc and click the "lvl up" button again. Rinse and repeat until you see skills you like.
Certain skills will only come up when you move the crew to the relevant crew slot, ie. canoneering will not show up as an upgrade until you move the crew member to the cannon slot.
Some skills cannot be trained and you have to buy crew that have those skills if you want them (you want them). These include:

Sharp Eyes - for the lookout. Shows you location of booty on beaches.

Gourmet Chef - +3 Crew morale instead of the usual +1. A 300% increase. That's 300% more chef per chef.

Expert Quartermaster - 50% less provision usage.

Master Cooper - No turn speed penalty from any amount of cargo. Really good if you like raiding ports. Which you do. Yarr.

Trained Surgeon - 35% chance to save a crew members life rather than the usual 10%.

For captain skills the best bet seems to be the strength tree. This will enable you to keep your crew alive during boarding action and port raids by the simple but effective measure of smashing in the skull of anyone attacking your shipmates on low health. You see a shipmate in trouble, ruining low on hp, go over and smash the face of whoever is attacking them. It takes a long time to level up the crew in this game, so your old ship hands are valuable. This seems to work way better than using the morale tree. After strength best best is to go for the attack speed tree for similar reasons. Then go morale. Boarding and raiding are when you will lose the most crew, so these are the skills you should prioritise for your captain. Although risky (be prepared to save-scum a few times) raiding ports is a great way to fill you ships hold and make a huge profit.

It's worth giving each of you crew a handgun and a shield. The shields increase their survivability (although all shields seem to work about as well in the hands of crew so just go with the cheapest.) The handguns are great as they enable your crew to take pot shots at flyers and sea monsters which really helps allot. It also means that some of your crew will actually do the smart thing and stay back taking pot shots during boarding actions. Giving your lookout a handgun or a rifle is a must as she will not be able to engage (or be engaged) in melee during a boarding action, so if you want her to be useful, give that b*tch a cannon. B*tches love cannons.

The game also contains cutlasses. While not a necessity, unless you are a pirate, you are a pirate, so they are a necessity. Yarr. For some reason I seem to find more of them in the Wasteland port, but that may just be the fickle whims or the dice god.

As for equipping your captain, get the best shield you can find, and buy her a hammer. as soon as you kill a megalodon, save one of the teef and take it to Mousillon. Then go to the weapon shop and buy the megalodon axe. Given the slow, clunky nature of the games melee system it seems to be the best weapon in the game. There is just no substitute for one-shotting your foes. Getting a blunderbuss, a Mienkopf, and a handgun is a good idea. I find I can sometimes get a good shot off with the blunderbuss when I start a boarding action (equip the blunderbuss while your ship pulls up to your victims to give you self time to load, then hop over and spew your load onto the face of the first enemy that steps to your crew). If you spot enemy up in the crows nest taking post shots it's a good idea to switch to the Meinkopf, and when that runs out you can switch to the handgun for one last shot. As long as you aim better than an orc this should be enough to take care of the problem. Similar strategy for sea monsters that chomp your ship. Rotate through the guns to get as many shots off as you can without having to reload, then just keep using and reloading the blunderbuss, as it does way more damage. Sometimes your captain will not have taken the time to re-load her guns beforehand, so it will just be blunderbuss all the way. Deal with it.

Although risky (be prepared to save-scum a few times) raiding ports is a great way to fill your ships hold and make a huge profit. Press Esc, open world menu, and check factions. You want to make as few enemies as possible so that you still have somewhere to sell your booty and upgrade your ship, so check to see who the billy no-mates is and then raid them. You want to make sure you are still friends with at least one faction that has a shipyard to make sure you can get all the upgrades. Shipyards are the ports with the little yellow anchor icon. If you ever figure out how the ♥♥♥♥ to join the pirate faction, let me know. In the meantime, just make your own pirate faction. With hookers. And blackjack. In fact, forget the faction.

Now that ye 'ave taken the time to listen to this salty old seadogs tale, I'll thank thee for the nip 'o' rum and be on me way. Go now, and make your own tales to tell.