It’s not often mentioned, that before there was Guinness or any beer in Ireland, there was Spanish wine. Merchants like the O’Malleys imported wine for generations, selling it to other merchants who came to the market town of Cathair na Mart, now called Westport, on the shores of Clew Bay in County Mayo.
Spanish wine from the northern area of La Rioja came through the Port of Bilbao, along with iron implements like swords, shipbuilding hardware, armor and munitions, wool, and very importantly, saffron for dying garments. Bilbao was an important center of commerce, along the trade routes from England, then to France, along the coast of Spain to Portugal and into the Mediterranean.
It seems there was quite a bit of sea shipping/commerce, which makes sense that all these countries have mountains, so hauling by horse or donkey would be arduous. There are no railroads yet, so carrying heavy loads would have to be on water. The sea must have been crowded.
Researching shipping competition in this era, I came upon the Desmond Castle in Kinsale in southern Ireland near Cork. It was built in 1500 specifically as a Customs House. King Henry VII of England granted the Earl of Desmond the right to levy a tax on incoming wine cargoes there. Kinsale later became one of sixteen ports formally designated for legal wine importing (1569), specifically to fight smuggling. Might this be where the Earl of Desmond captured Gráinne?
Here’s my working theory on “smuggling”: I think it was really just established import businesses that the English couldn’t reach — not anything hidden or set up to dodge taxes. The English with their ocean-going ships couldn’t get into Clew Bay with its shallow waters and drumlins, so my guess is that’s part of why they leaned on words like “piracy” and smuggling to justify raiding Irish holdings they couldn’t conquer. I’m still working out how well the sources back this up — it’s an open question on my end right now.