DeMarco Meets With Tad
On Day 5, at nighttime, DeMarco went to get a drink at The Unicorn — the tavern of Ancient Spire Outpost. DeMarco was very anxious and kept checking his pocket watch for his next meeting.
To cross the Devil's Shroud, DeMarco needed supplies. He left Ancient Spire to meet Tad — shopkeeper on Morrow's Peak Outpost — on The Devil's Thirst at midnight by the northern-most campsite, which leads to Day 6. Tad was not happy about this encounter on this dangerous island but still brought the requested supplies to DeMarco who was constantly checking the time on his pocket watch.
On Day 7, DeMarco went to an unknown place to leave his mark so the Sea of Thieves could remember him.