I have a player who has created a smuggler companion based on the Mediterranean. I'm interested in any knowledge people have about smugglers in the middle ages.
I would presume that any big, walled city would impose tariffs on goods coming into the city.
Any thoughts on various methods to smuggle goods into a city from a ship coming into port?
These are my iniatial thoughts:
-- bribes
-- go in through the old Roman Sewers, if they exist
-- tunnels under the walls
-- disguise the goods as something else
From the research I've done (minimal, and all dealing with smugglers in the 1800s), most ships would anchor in a cove, then transport the goods overland to local villages, usually employing the villagers directly. I'm interested in trying to get goods into walled cities.
That's not generally true. Towns usually had no objections if people from the countryside brought their wares there and sold them to the citizens. Quite to the contrary, their existence depended on that trade.
During market or fair days, when everybody could sell to everybody, the protector of the market - be that king, duke, bishop, town or somebody else - usually imposed a toll on wares going to market, and also often required that all transactions were made with the coins he had minted and for which hence at the market other coins had to be exchanged first. But that was - at least ostensibly - because he protected the market, sent his judges to the place, and made sure measures were right and nobody was cheated.
Towns also often waived their market taxes for citizens of allied towns which did vice versa the same, and other market protectors could waive the tax by way of privilege to individuals and groups.
Smuggling wares into a city to bring them to market does not make much sense: they would be discovered on the market place.
Guilds, when sufficiently powerful in a town, could impose bans on certain imported products, both to protect citizens from low quality wares and to protect the income of their members. But in that case bringing in such products would be far easier then selling them in the city.
In general medieval tolls and taxes were designed so as to be easily enforceable with little personnel, like bridge, road and river tolls or market and fair taxes: no good environment for the smuggler.
Again, you have to do your own research on the laws and customs at the time and place of your campaign, of course. Once that's done, you can design business models for your smugglers. Just do not expect to find many.