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Hey everyone, new to the forum, but figured I would add my knowledge here. Sailing is the best thing I do, and I'm finding more and more people I know asking me to sail them, because they just can't seem to engage enemies correctly, or they just can't get through an area without getting sunk . I hit Sailing MASTERED (level 25), while I was only at Level 25 rep (notoriety). I use different tactics depending on what ship, if I have a crew, and what we are trying to engage. So I will list somethings to help you get a better handle on sailing.

One of the biggest problems I see with people sailing is they try to get in as close as possible to the highest level ship they can find near them. Make a point not to do this. Higher level ships do give the best plunder, but they also can sink your ship quickly if you make a mistake or you do not know what you are doing. Stay away from war sloops or sloops above level 12. They can shoot fire at you and are fairly accurate. They will also outsail you because they are very agile. Practice before engaging them. Once you can take down a level 25 war frigate on your own without taking much damage, then you might be able to try your hand at a war sloop. Just know that sloops above lev 12 can be difficult to get consistant broadside hits on and they shoot FIRE at you. They are agile and will alter their path quickly to engage you. Unless you have great speed with your ship, they will catch you and pound you before you can sink them.

Quick tips to know...

If you are going to be the captain and sail, max out your broadsides, it makes a huge difference.

As captain, you are in command of the ship. Take on that leadership role. You are the only one able to see all around the ship. Whether you are sailing your ship or a friends ship, once you take the wheel, lead your crew, be firm in your orders and the targets you engage, and remember, they are trusting their lives to you, so do your job and keep them safe. Very rarely is it the fault of the crew if your ships sinks.

The Take Cover and Ramming Speed skills are a must, but you only need 1 point in each to take advantage of these for sea combat. Use them for protection, especially ramming speed. If you are receiving incoming fire from enemy ships, especially FIRE cannonballs from enemy ships, use your take cover just before it hits your ship. If you do not have take cover or you have already used it, and fire is heading towards your ship, hit ramming speed to move out of the way.

DO NOT fire your broadsides at an enemy until you have lined the side of the ship up with the enemy you wish to engage. You have to allow the broadsides a chance to lock on. If you fire too early, you wasted a chance, firing at the right time or even late will work, so better late than early needs to be your thinking.

One thing you need to know, other than flag ships, all enemy ships ships circle. Some turn left others turn right, but the fact is they circle. If you are in a galleon or a Frigate, try to engage on the INSIDE of that circle path. If you are in a sloop, engage from the OUTSIDE of that circle path. This gives you the advantage.
When in a frigate, let the nose of your ship take the damage, that is the strongest area of that ship. So turn the nose to take incoming fire from the enemy.
When in a galleon, the rear of the ship is the strongest, so turn the rear of the ship to take incoming fire.
When in a sloop, there is no strong area of the ship, so use its speed and tight turning to reduce hits from incoming fire. Stopping once an enemy fires is often a good idea as enemy ships fire ahead of a sloop thinking it will run into the cannonballs.

Patience is the biggest key to your successful sailing. Wait for that perfect shot. Wait for the enemy to turn their back on you. Wait for them to make a mistake, and yes, in EVERY battle, that enemy ship WILL make a mistake. It is a computer player and was designed to do that to give you the chance of beating them. The higher the level is on the ship, the longer it will take for them to make a mistake. But they will make one. Either they will turn wrong, or they will fire too early, or they will fire too late. Look for those opportunities, and make them work to your advantage. Once they make that mistake, you can cause them to continue making that mistake. If they fired too late, turn in on them a bit to give yourself a better shot. If they are firing too early, delay your turn to circle them. If they turned incorrectly, you can actually stop your ship most of the time to get 2 clean broadside shots off before they correct themselves.

How to engage

First off, I am a galleon sailor. I love the cargo space and love plundering. I myself have a war galleon. The galleon is a plundering ship and the Galleon class ship has the most broadsides of any ship in the game, especially the war galleon. If you sail alone, the galleon is a good choice because even without a crew on cannons, the galleon can still beat up most other ships.

If you are alone on your ship, you need to engage from medium to long range with broadside, and keep the ship on the move. try not to stop unless the enemy ship is heading right at your broadsides. If you are in any class of sloop, this does not apply, as when sailing a sloop during combat, you must stop and start your ships again and again. You don't need to worry about loosing speed by stopping in a sloop, because it is fast and picks up speed quickly.

If you have a crew, you pick the side to engage from, not your crew, remember tip above about engaging INSIDE or OUTSIDE on the enemy path. Then tell your crew which side, so they can man the cannons on that side. With a crew, you can engage much closer, so try short to medium range.

It is best to run up on enemy ships from their rear. Be careful though, as if you get too close, the enemy ship will recognize you are engaging them before you fire a shot and will turn to engage you. What works for me is the following. I charge towards an enemy ship from behind. Once I have them at a decent range, I stop my ship, then turn my broadside towards their rear. I open fire, then wait to see which way the enemy ship is turning. If the enemy ship turns in the direction my ship's front is facing, I sit and wait for my braodsides to recharge and fire off another round. I then either open sails to move forward or hold down my "S" key down, which moves my ship in reverse. Although it is very slow, it is usually enough rear movement to mess up the enemy ship cannon fire. If the enemy ship turns in the opposite direction as the nose of my ship, I open sails and begin making wide chasing turns, making sure to spoil any broadside chance my enemy might get on my ship. You will know if you are spoiling the enemy broadsides if they open fire and their cannon fire flys way behind your ship.

Ship Classes

Lastly I will give you important info regarding use of your ships. For anyone lower in level, you may think having one of each ship type is out of the question, but one day you will have the gold to do so, and I highly recommend it. Each ship type has a specific job and they perform best if you use them properly.

The Frigate Class.
This type of ship is built for fighting with a large crew, (4 or more not counting the captain). It carries the most on deck cannons of any of the classes and is meant for large crews. The captains job with this ship is just to get his/her crew lined up for shots and try not to move the ship back and forth too much. Use the nose of the ship when engaging. You have 2 cannons on the nose, so tell your crew to get on them. Whoever you get on those cannons, tell them to stay put, not to jump to other cannons. If you are using your frigate properly, they will be able to get plenty of shots off. Keep that nose at the enemy as much as possible, turning only to get a brpadside shot off now and then. The nose is the heavy armor of the ship and is meant to take the beating. This ship is meant for long, heavy battles at sea. Ship of choice when you have a lot of ships to sink and you have a crew. With a crew, you can engage more than 2 enemy ships at a time.

The Galleon Class.
This is a plundering ship, but can hold its own in a heavy battle. This ship carries the most broadsides and cargo space, plus works good with or without a crew. If you are sailing a galleon, worry more about lining up your shots rather than your crews shots. Just tell the crew the side you are firing from and they will get their shots in. Protect the hull as much as possible and use the rear of this ship to take the beating. It has heavy rear armor. But if you take damage, you do not need to fear it much, this ship can take a decent beating. This ship is meant for plundering gold. Head out, sink ships until the cargo hold is full, then port, repair, and head back out. You should not engage more than 2 ships at a time.

The Sloop Class.
This ship is meant for gun and run tactics. This ship is built for pure speed. It has the least amount of on deck cannons and broadsides. It turns tight and gets up to top speed quickly. The proper use of this ship is not to stand and fight, but to stop and go, fire and run, then reengage. This ship is good with or without a crew, but it is much better with a small crew. Your crew will need to stay on the run between side cannons. Your job as captain is to keep this ship safe and take the least amount of damage you can. Your crew should be watching how you are moving the ship to know which side to fire from. Make long fast runs, pass by the enemy at mid to close range, fire your broadside while your crew fires the whole time. Once you get slightly out of enemy range, make a tight turn and head back in again. Continue this until you sink that ship. This ship is meant for running you from island to island quickly. It is not meant to be a battleship. The only reason this ship has cannons and broadsides is to defend itself, not to fight. If you like the sloops speed, but want to fight at sea, save up for a war sloop. The war sloop can take an average amount of damage and is great for taking on enemy sloops. It takes some practice to get the hang of engaging using the war sloop, but when done right, this ship is quite effective at taking on ships when using run and gun tactics. Never engage more than 1 ship at a time, and if other enemy ships are approaching, get of out there quickly. This ship will rarely survive multiple ships engaging at once.

I hope this was all helpful. If I find it has been, I will try to add some more specific info and tactics for each class.