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I've just recently gotten into playing the Dragonborn questline, and my usual pattern is to explore/quest around Solstheim until I'm overloaded with loot, and then travel back to Skyrim to my house to unload.

It's been convenient that I've had Arvak since before getting heavily into Dragonborn, so I can still fast-travel when overloaded.

It just recently occurred to me that I didn't know what the "slow-travel" options are for getting between Solstheim and Skyrim. Investigating, the only options I could find were to buy a boat ticket. According to a wiki discussion-page comment, swimming between Solstheim and Skyrim is not possible.

So, apparently, making the trip is free if you're not overloaded or have a horse, but otherwise, it'll cost you.

(Search terms: northern maiden, ferry)

Okay... a wiki talk-page comment says that it's not even possible to ride the Northern Maiden when you're over-encumbered, same as the limitation with carriages. I didn't actually try, but I did talk to the captain, and he offered to take my money. I'll have to test this properly to verify.

So, in the name of science, I did some experiments. If I talk to the captain while overencumbered and ask for a ride from Solstheim to Skyrim, he takes my money, tells me to load up and get comfortable, and then nothing else happens. What I'm guessing happens is: when I purchase passage on a boat or a carriage, after subtracting the gold from my inventory, the game engine executes the fast-travel subroutine to get me to the destination. When I'm over-encumbered, the fast-travel subroutine says "nope, they're overencumbered", and the game silently does nothing, not even refunding my money.

I also tried some workarounds. If I drop some items onto the deck of the Northern Maiden, I can then successfully purchase passage, and the trip actually happens. Unfortunately, the items I dropped onto the deck disappear in the process.

Second experiment: stow the items in one of the fish barrels on the Northern Maiden while in dock in Solstheim. Now that I'm not over-encumbered, successfully buy passage to Skyrim. When I arrive in Skyrim, the fish barrel no longer contains my items.

Third experiment: after stowing the items in the fish barrel in Solstheim, and finding them gone when I arrive in Skyrim, I purchase another ticket back to Solstheim. When I arrive in Solstheim, lo and behold! -- my items are back in the fish barrel again.

Theory: when I take a boat trip between Solstheim and Skyrim, the boat doesn't actually make the trip as well. There's actually two pretty-much-identical Northern Maiden boats, one in Solstheim and one in Skyrim. The 250 gold buys me access to a teleporter that takes me between the Solstheim Northern Maiden and the Skyrim Northern Maiden. When I stash an item in a fish barrel on the Solstheim Northern Maiden, it doesn't appear in either of the fish barrels on the Skyrim Northern Maiden, because those are different fish barrels.

I like this type of information. There is a bug note on the ferryman’s page, but I learned this from your post. Do you know if the other ferryman also have this encumbrance bug and also keep your money? It kind of makes sense that carriages and ferrys might have weight limits, but if they don’t respond with a proper notice or dialogue, that’s a bug.