Vicente Valchieri's Quests

Vicente is in the lowest level of the Sanctuary. If you speak to him, he'll tell you of his vampirism, and offer you the first contract for the Dark Brotherhood. He'll also tell you to get into the habit of asking your fellow brothers about your contracts, as they may have some insight into your tasks.

A Watery Grave

Your task here is to board the Marie Elena in the Waterfront district of the Imperial District and kill the captain, one Gaston Tussaud. There's no chance for a bonus for this first quest of yours, so no need to worry about that. Just head to the Waterfront district, and bring along some potent weaponry.

When you reach the waterfront, find the Marie Elena, but don't speak to any of the pirates here. If you wish to take a stealthy approach to boarding the ship, head to the end of the path and find the open shipping container. You can hide inside of it and sneak on board that way. Alternately, you can just hop onto the ship and try to find a passage inside, but doing so will cause all of the pirates near the ship to become hostile to you. If you do choose this path, wait until an Imperial Guard is walking past, as they'll help defend you.

Jumping across to this balcony on the ship will let you easily kill the captain.

Alternately, you can try to reach the entrance to the Captain's Quarters at the very rear of the ship, but getting to the little balcony will require you to jump from atop the open crate. You'll also have to pick a five-tumbler lock, but heading in this way will position you directly behind Tussaud, allowing you to sneak attack him, or just slip a Poisoned Apple into his inventory and wait for him to keel over.

If you do decide to sneak on board via the crate, though, you'll have to kill a pair of pirates before reaching Gaston. You may want to wait for their conversation to cease before doing so, as that will allow you to kill them in their rooms and possibly sneak attack them.

Regardless of how it happens, when you kill Tussaud, two of his pirates will burst into his room. They won't detect you if you're sneaking, allowing you to avoid them as you wish. You can nab Tussaud's key from his body, allowing you to open his booty chest, as well as the rear door if you wish to escape out of it. All of the pirates near the ship are now hostile to you, though, so be ready for a fight when you leave! It's best to do this quest in the middle of the day, since guards are more likely to be present then. If you find the pirates to be too much to handle, run to another district and let the guards eliminate them.

Accidents Happen

Watch out for Gromm, who stands vigil over the corpse after you leave it.

Return to Vicente and grab another quest from him. Your target this time is Baenlin, who lives in Bruma. To earn the bonus for the quest, you've been asked to enter a crawlspace above where Baenlin and loosen the bolts holding fast a mounted head that's fastened above where Baenlin eats dinner. Doing so between the hours of eight and 11 PM will cause the head to fall on Baenlin and kill him. If you kill him in any other manner, or if you kill the manservant Gromm, then you lose the bonus.

If you want to have a good chance to loot the house before killing Baenlin, enter in the middle of the night, around two AM or so. You can enter through the basement door at the rear of the house, if you wish; there are plenty of food items in the basement with which to make Restore Fatigue potions, if you're looking to increase your Alchemy skills. Explore the house, stealing anything that you like, then sneak upstairs and look around. There's a jewelry box on Baenlin's dresser. The crawlspace entrance is in Gromm's room, though; open it, head in, then close it behind you. Wait until 8:30 or so, then loosen the fasteners to drop the head onto Baenlin.

Now, when you kill Baenlin, Gromm will move to the body and stand there. He doesn't really move, making it a hopefully easy matter to sneak past him to the entrance to the basement and leave the building. Even if he detects you and attacks, you should be able to keep the bonus to your mission by exiting the building right quickly.

Return to Vicente for your reward: the Sufferthorn dagger, with Drain Strength and Damage Health enchantments.