Tag Archives: Pirates week

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

The History of Pirates Week on the Grand Cayman Island

Each November, Grand Cayman Island transforms itself into a 17th century pirate encampment as it celebrates the island’s heritage of pirate legends and lore. The festivities at the 11-day Pirates Week event include mock “invasions,” parades, costume contests, food and drink specials at local restaurants and treasure hunts.

About Pirates Week

Although the Cayman Islands were first found by Europeans when Christopher Columbus set anchor there in 1503 on his fourth journey to the New World, the islands did not “belong” to any country until they were ceded to Britain in 1670. This made the three-island chain an ideal haven for pirates and buccaneers. The golden age of piracy in the islands spanned from the 1650s to the 1730s and some of the most notorious pirates of that age, including Edward Teach (aka Blackbeard), Lowther, Lowe and Morgan, called the Cayman Islands home. In addition to the lack of organized government, the abundance of turtles for food, small coves for hiding ships and treasure, and the general lack of other inhabitants make the islands attractive to pirates. Though the pirate era lasted less than 100 years, it has captured the imagination of generations of Cayman residents and visitors alike.

In 1978, the Cayman Islands Tourist and Visitors Bureau launched the Pirates Week festival as a way to draw more tourists to the islands. A few years later, the popularity of the “Pirates of the Caribbean” movies helped to bolster interest in the event. Today, Pirates Week, now in its 38th season, draws more than 35,000 visitors to the Cayman Islands each year. It is the islands’ largest celebration.

To be a part of Pirates Week this year and stay along Grand Cayman’s Seven Mile Beach, contact South Bay Beach Club at soutbaybeachclub.com or by calling 407-992-2844.


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  • February 8th, 2016