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Background
You'll receive this quest when you learn of the riverboat, which is located southeast of the
Arlington Library. There isn't a level requirement for the quest, so you can receive it at any time after leaving Vault 101.
Walkthrough
As you approach the boat, you'll be stopped by a woman named Catherine. She'll ask you to look for her daughter Nadine, and she'll tell you that Nadine has bright orange hair. You won't receive a quest for this, but searching for Nadine is tied in with the main questline for the DLC, and so you can do both at the same time.
On board the boat, you'll meet the ferryman Tobar. He'll tell you a little bit about
Point Lookout, including its "ruins of ancient please towns" and "mysterious swamps bristling with treasure," but mostly all you'll be able to do with him is buy a
Riverboat Ticket for about 300 caps. When you're ready to go to
Point Lookout, just buy a ticket and then sleep on the cot in the passenger cabin.
When you arrive at
Point Lookout (#1), you'll see smoke billowing from Calvert Mansion (#2). Tobar will comment that the mansion is supposedly haunted but also "full of pre-war treasure," and the quest will update, giving you an objective to investigate it.
Inside the mansion, you'll see a ghoul named Desmond and a pair of dogs being attacked by tribals. Desmond and the dogs can't be killed, so don't worry about wounding them with friendly fire. Just lay into the tribals.
Note: If you explore Desmond's command room, then you'll find lots of weapons and drugs, including a
Flamer and a
Minigun.
After the battle, Desmond will ask you to defend the rest of the mansion. This will require you to locate two holes in the roof that the tribals are using to get inside, and find a way to seal them. You'll have to seal the western breach first, and then the eastern breach. In both cases, you'll just need to kill some tribals and then blow up a red boiler-like object in a barricaded room (by shooting it or by using a grenade on it).
Note: Shooting the boiler will cause a huge explosion, so stand as far away from it as possible when you seal the breach.
After sealing the two breaches, Desmond will lead you to the entry hall, where you'll have to defend against four more attacks (coming from the upper right side, then the lower right side, then the lower left side, and finally from the front door). Desmond will suggest that you lay down some mines, but we'd recommend against it since any that don't explode might get triggered by Desmond's dogs after the battle.
Once you've completed the defense of the mansion, when you talk to Desmond again, you'll receive the Superior Defender perk, plus 300 experience points, and Desmond will give you the next main quest,
Walking with Spirits.
1 - The Duchess Gambit
2 - Calvert Mansion