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I had a long-running game and applied the Empire of the Skies DLC to the game when it was released.
The quest to build the Iron Tower from Tourist Season was already in progress. The tower is located in Crown Falls. I progressed the quest chain to the "A Trifling Matter" part. When you reach the part marked "A Trifling Matter: Another Conspiracy Unmasked", where you must deliver the "Chained Conspirators" quest item to Archibald Blake at his lighthouse in the Old World, the quest will not progress when the item is brought to the quest marker. The quest text reads "Bring the Conspirators to Sir Archibald Blake's Lighthouse".
Things I've tried:
Delivering via different steamships.
Delivering via airships.
Moving the quest item between ships
Transporting the quest item out of the session and back in.
Putting the item back in the Crown Falls inventory and taking it out again.
Moving ship pixel by pixel to see if accepted range is very small.
Rolling back and trying again from the previous stage of the quest.
Rolling back and selecting the other options for "A Trifling Matter" where you must deliver the "Rebellious Worker" to Archie instead. Same problem.
Clicking the lighthouse
Clicking the harbor building
Clicking everything
Throwing item overboard and picking it up again
Abandoning quest (results in the Iron Tower never able to be finished)
Rolling back over 36 hours to the beginning of the Iron Tower chain. The same problem occurs again.
DLC:
Seeds of Change
Empire of the Skies
Sunken Treasures
Botanica
The Passage
Seat of Power
Bright Harvest
Land of Lions
Docklands
Tourist Season
The High Life