I've been thinking about what Rare may do with the Monkey Island crossover, and I wanted to speculate on what I think may happen using what we know from the trailer, the interview on Xbox Wire, and the newsletter post.
Newsletter: https://www.seaofthieves.com/news/discover-the-legend-of-monkey-island
I think the 'voyage' would start in the tavern alongside the beginning of the 'Shroudbreaker' quest. (you would vote on the voyage in the tavern) The story would start with Guybrush and Eliane entering the tavern and requesting help returning to Mêlée Island. The interview says that the story picks up where the Easter Egg in A Pirate's Life left off; I figured that Guybrush and Elaine would get lost on their honeymoon and seek out hired help (That would be us) to guide them back to Mêlée Island.
Based on a Tweeted reply from Mike Chapman (https://twitter.com/ChappersChapman/status/1668021712720470021), I think LeChuck may have tracked Guybrush and Elaine to the Sea of Thieves, dragging us into conflict with him in the process. (I'm going to guess, as we sail away from the tavern, we'll be chased by LeChuck into one of the Sea of the Damned portals, sending us into Guybrush and Elaine's memories of Mêlée Island and Monkey Island) I think we'll get separated and find Kate Capsize somewhere lost in the underworld before helping her get back to the mortal world.
I'm not sure what may happen next, but I think it would be really cool if LeChuck and Flameheart had a 'mutual handshake' moment (kind of like Ryu and Cyclops from Street Fighter x X-Men or Sora and Mario from Smash Ultimate) and join forces to try and conquer the Sea of Thieves together. I think it will be left as a cliffhanger of sorts; Flameheart will finally make his presence known across the Sea of Thieves in the aftermath of the Tall Tales, with LeChuck somewhere behind the scenes gathering support.
I'm convinced we'll see or hear from Jack Sparrow in some capacity. (the Black Pearl is obviously in the trailer among the ships in Stan's used boat lot...my guess is that Jack heard about Pendragon's fate and went to try and rescue him, leaving the Pearl unoccupied for Stan to steal find) Going along with the cliffhanger idea, I think the third chapter of the Tall Tale ends with us sending a message out to Jack for help. (meanwhile, the Adventures will continue telling the Dark Brethren's story and what's happening with Briggsy and the temple)
I think this is all building up toward the Avengers: Endgame of Pirates; with Flameheart and LeChuck causing mayhem in the Sea of Thieves, we'll make contact with Jack and call in that favor he owes us. I have to imagine Jack's rescue attempt will be unsuccessful, so we'll introduce him to Guybrush before tagging along with the two of them to rescue Pendragon. Afterward, we'll have a climactic three-way war (between the Athena's Fortune + Jack and Guybrush, The Dark Brethren, and Flameheart and LeChuck) over the Sea of Thieves/Caribbean in a third set of Tall Tales sometime in the future.
I guess we'll find out soon enough! I am ecstatic for this to release! I know this may be a controversial opinion, but I think launching the Tall Tales one month at a time is a good idea; it helps spread out the content for the season and allows each of the three chapters breathing space to stand apart on their own merits. Besides, we have the next Adventure coming up; we'll have a lot of things to look forward to over the course of Season 10!
