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Pirates Week Events, Part One!

The 42nd annual Pirates Week extravaganza will return to the Cayman Islands this November for another five days of buccaneer-inspired fun. The “invasion” starts on Cayman Brac on November 1st and goes to the 3rd. It hits Grand Cayman from November 7th through the 11th and ends on Little Cayman from November 15th to the 17th. Find out what you need to know about the rocklicking festivities to plan your Grand Cayman adventure accordingly.

Pirates Week Happy Hour On Grand Cayman

Grand Cayman offers plenty of pirate-tastic ways to spend your vacation days. Even though the first “invasion” takes place on Cayman Brac, Grand Cayman hosts a Pirates Week Happy Hour and Official Kickoff Party on Thursday, November 7th. Say cheers starting at 4:00 pm and don’t worry if you get there late since the event goes till 2:00 am. It happens at the Royal Palms Hotel and features plenty of island beats for dancing the night away. The free event also features numerous visiting pirate friends.

5K Run/Walk

The Pirates Week 5K Run/Walk starts at 5:30 pm in front of the South Terminal before making its way south on Harbour Drive and South Church Street. It finishes at South Terminal and includes awards for the top three men and women in each category. The first 50 registrants will receive a free t-shirt. It’s $25 to enter this fun run.

Food Festival

What’s Pirates Week without traditional marine fare? The Food Festival on Friday, November 8th on Shedden Road includes turtle and couch stew among other Carribean dishes, as well as Asian and Hispanic cuisine. Sample your favorites starting at 6:00 pm, with the event ending at 2:00 am.

Fireworks Cruise

No Pirates Week is complete with the Fireworks Cruise. Climb aboard the Carib Dauntless to marvel at the colorful, fiery display in the sky. Boarding begins at 6:00 pm and the boat heads out at 7:00 pm. The fireworks start at 8:00 pm.

Pirates Landing Cruise

The pirates officially invade Grand Cayman on Saturday, November 9th, causing a wonderful commotion complete with tons of confetti. You can even participate in the invasion! It’s for adults only, costs a mere $15, and you can bring libations aboard.

These are just some of the Pirate Week events happening on Grand Cayman. Don’t miss Part Two of this blog series for more information about this annual event celebrating the Carribean’s unique heritage.

Reserve your luxury hotel on Grand Cayman today by visiting South Beach Bay Club.

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  • October 30th, 2019
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Cayman Islands Pirates Week Runs And Swim

The weekend of November 9th to the 11th will be an active one on Grand Cayman as amateur and professional athletes take part in various Pirates Week runs and swims.

On Friday the 9th, Grand Cayman residents and visitors will be able to take part in the 2018 Pirates Week 5K Run, a race running along Harbour Drive, starting and finishing in front of the Grand Terminal.

Saturday the 10th, at Governor’s Beach, locals and tourists will participate in the Pirates Week 5K Sea Swim Grand Cayman, the Cayman Islands’ oldest swimming tradition – an event that will award 3 female and 3 male contestants with prizes.

Pirates Week 10K “To Hell and Back” is the finale to Pirates Week’s athletic activities. This race starts at Kimpton Seafire Hotel and promises to be a thrilling occasion to watch and to participate in.

Pirates Week 5K Run

Cayman Islands’ Pirates Week 5K Run begins promptly at 5:30 p.m. on November 9th. Registration is currently open online and there is a $25 entry fee (or $40 total for those entering the 5K and 10K on November 11th).

Late registration on race day is possible from 3:30 p.m. to 5:30 p.m. in front of Grand Cayman’s Bar Crudo. Participants in this race are timed, water is available along the course and runners may bring their dog companions to race with them.

Pirates Week 5K Sea Swim Grand Cayman

On Saturday the 10th from 7 a.m. to 10 a.m., the Pirates Week 5K Sea Swim Grand Cayman will be a fun event to watch and enjoy. This annual tradition is going on its 31st year in Grand Cayman and it’s a celebration of island life.

The Pirates Week 5K Sea Swim Grand Cayman combines the excitement of Pirates Week festivities with an open-water race that is truly an experience unlike any other. Race caps are provided during registration and swimmers must wear them during the race.

This race is one full 5K loop. Refreshments, T-shirts and trophies are given.

Pirates Week 10K “To Hell and Back”

If you dare to run in Pirates Week 10K “To Hell and Back” race, check in at 6 a.m. on Sunday, November 11th. The race starts at 7 a.m. sharp. You’ll start at Raleigh Quay Road not far from South Bay Beach Club and you’ll travel on West Bay Road, Town Hall Road and then Hell Road with a turnaround at Devil’s Hangout before retracing the route to end at Calico Jack’s.

Registration for Pirates Week 10K “To Hell and Back” is $25 online.

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  • October 30th, 2018