Catch up with Achilles by the port in Davenport. He'll introduce you to a captain but then you'll simply have to return to Achilles. After that, Achilles is going to explain how the ledger works in the manor. Buying and selling things through the ledger is a great source of income when you get it going.
Several months will pass and you'll find yourself on the Davenport Homestead once again. Use your new horse whistle tool to summon a horse and then ride on over to the Harbor. When you get there, the old captain will be back on his feet and with a good ship to boot. Talk to the captain again and you'll learn how to be a sailor.
The controls for the boat are simple enough. The Jump button increases the speed of the ship (No Sail, Half Sail, and Full Sail) while the parry button will reduce your speed through the same measures. On the radar, you'll notice a large green cone that indicates the direction of the wind. The wind moves from the wide part of the arrow to the narrow part and a pulse of bright green will move along the cone to indicate this. This is important for times when you can't see the entire cone clearly.
Use the left stick to steer the ship and the right stick to look around. You're sailing off for Martha's Vineyard to find some officers to man your new cannons. On the way there, be careful to avoid any rocks. One of the constraints is not taking damage on your trip. It may be slow going but if you are unsure of the waters, slow to half sail and follow other ships to be sure the waters are safe.
Make your way through this straight and then turn to port (left) to come into the island. When you get close, the captain will call for no sails. When he does so, kill your speed and then keep tapping the button to stop completely.
After paying a visit to the tavern, you'll sail back into the bay area and find a couple of busted ships for target practice. At this point, you'll be taught the finer points of shooting. When you are done and are sailing out to sea, you'll be attacked by a few ships and be forced to fight.
There are a couple of constraints on this section of the memory including bracing properly three times and taking out two ships with the swivel cannons. You'll have to use the swivel cannons on these first few ships so just use them exclusively until you sink the two ships you need. You won't learn to brace just yet. Shooting at a ship that is moving is a little bit more difficult than stationary targets. It is usually best to aim just behind the ship, the swinging the ship around so that your line of fire (depicted by the white highlight) is in front of the ship by a little bit and then pulling the trigger. Sometimes you will be close enough that you won't need to lead much or you may be able to arrange it so that the enemy ship is headed directly at you, meaning you won't have to lead but most of the time, it's best to shoot as if there were a ship directly ahead of the one you're trying to hit.
After clearing out these first few ships, you'll be attacked by another rather large ship. Now you will learn to brace by hitting what would otherwise be the attack button. The enemy ship preparing to fire will be shown by a red highlight over the water which will quickly be followed by someone on your ship yelling for everyone to brace. You cannot brace properly if you are in the middle of shooting so shoot and get ready to brace between shots. You'll have to accept that you're going to get hit a couple of times getting this restraint so hit the ship a couple of times but don't finish it. Brace successfully three times and when you've done that, finish of the enemy ship by alternating the main guns and the swivel guns in between reloading.
The ship will automatically return to harbor and when you get there, head back to the Davenport Manor to talk to Achilles once more.
