Nothing says pirate event like standing on a sandy island under a palm tree, watching two tall ships firing cannons at each other on a warm night in December.
I was in Key West for the Fort Zachary Taylor Pirate Fest, part of the larger Pirates in Paradise festival.
The larger festival is purely "pirate" (or polyester pirate as some people call them). It included Captain Hook and a pirate Santa Clause. The part of it in the fort was focused much more on history although there were still some ren fair pirates.
The historical pirates had our own camp, officially the "careening camp". The idea was that we were camping on an island while our ship was being careened (this involved beaching the ship and scraping the growths off of the sides for extra speed). The festival continued into the fort with a couple of dozen vendors. These ranged from the same suttlers who set up at any historic event to a Utilikilt vendor (modern kilts).
The festival ran for four days. Each day had an attack on the fort. The first two days the pirates attacked unsuccessfully. On the third day they succeeded in capturing the fort. On the fourth day the British tried to recover the fort but failed.
The pirates were armed with small arms, mainly pistols and blunderbusses, and cannon. The British had more muskets and rifles and their own cannon. The pirates were aided by the tall ship, the Wolf which also fired on the fort.
There were three different two-masted ships that were part of the festival. At sunset each day they sailed past the camp, often firing on each other. There was also some firing from the walls at sunset most evenings.
Key West had a holiday parade on Saturday night and most of the pirates joined in that. I took a cab with a couple of others. We ran into a few more pirates near the start of the parade and decided to wait there. By the time the pirate unit went by we had around 20. Other pirates kept joining. I would guess that there were around 100 by the end of the parade.
On Sunday night the fort held a pig roast for the participants. The was accompanied by a "dead man's chest" auction to benefit the site and a show of some of the photographs that had been taken during the festival.
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