Pirates Week gets under way

Pirates Week

Don your hats and boots and try to find a friendly parrot to sit on your shoulder – the pirates are invading this weekend. 

The black flag of the Jolly Roger, a flag that once could have gotten a man hanged around these parts, now flies along the streets of George Town to welcome the thousands expected to invade the waterfront Friday and Saturday for Pirates Week. 

Forecasters with the Cayman Islands Weather Service expect partly cloudy skies and some rain showers around Friday and Saturday, with some possible thunderstorms on Friday. Pirates coming in by ship will face some east to northeast winds at 10 to 15 knots, with moderate waves. 

Friday’s events start with a 5K run in the afternoon at Grand Cayman Beach Suites, and then with a food festival along Shedden Road beginning at 6 p.m. 

At 7 p.m., junior pirates take center stage on Harbour Drive during the children’s pirate costume competition for the chance to win cash prizes and a ride on a float in the parade, and then Cayman’s wannabe royalty will vie to be crowned Miss Festival Queen. A fireworks show will light up George Town harbor Friday night beginning at 8:30 p.m., and then festival-goers can party until 2 a.m. at a street dance on Harbour Drive. 

Saturday at 3 p.m. will be the time to watch the horizon for the black flags approaching Hog Sty Bay. When the cannons start going off and two ships loaded with pirates invade George Town harbor, keep an eye on the faux governor. He or she is always the first captured when the raiders descend on Grand Cayman. 

Red Bull athlete Alex Mason, a “slackline” walker, has been brought in for the event by the Cayman Islands Brewery. Slacklining is a more extreme form of tightrope walking, and Mr. Mason is known for doing flips and other tricks on the rope. 

He will be performing as part of the pre-landing entertainment that starts at 2 p.m. on Saturday and at Pedro Castle on Sunday. 

Saturday night will be turned over to the pirates with another street party along the waterfront.  

The pirates will have the run of the island for a week until they’re finally put on trial for their crimes and misdeeds on Nov. 21. 

A number of roads will be closed in central George Town starting at 3 p.m.  

Friday through early Sunday morning.  

The road along the waterfront and most roads leading to it will be closed, so motorists should avoid the area. 

Scenes of rum swilling pirates and wenches owe more to the histories of Jamaica and the Bahamas than the story of the Cayman Islands, say historians. - Photo: Stephen Clarke
The Jolly Roger delivers a load of bloodthirsty pirates to central George Town.


  1. Now is the ideal time for Government to monitor the traffic in central George Town. The chaos and gridlock that occurs will give them good idea of what will happen when roads around the harbour are pedestrianised.Our roads in the capital are already at maximum capacity and one or two cosmetic adjustments to the network will make little difference in substituting for the arterial routes that will be lost to suit a few greedy merchants. The rights and convenience of local residents should take priority.

  2. This doesn’t exactly seem to be packing the tourists in. I just checked online and found plenty of room availability. There are even some price reductions next week. Makes you wonder if PW is all getting a bit stale, doesn’t it?