March 29, 2023

Cayman Islands Pirates Week 2016: The Age Of Romance

Pin It

dscn2727Now in its 39th year Pirates Week’s chosen theme is ‘Age of Romance’. This aligns with the Caribbean Tourism Organization’s mandate, calling 2016 the Year of Romance throughout the entire region.

The most famous of the Pirates Week festivities is held in Grand Cayman (Saturday 12th November) where spectators and pirates alike can enjoy the mock ‘pirate invasion’ from the sea at Hog Sty Bay.

Traditionally, boats loaded with pirates come ashore and ‘capture’ the island’s Governor – taking over the islands for an entire week before being ‘kicked off’ once again.

This year, the narrative of the landing pageant has changed to align with the Age of Romance theme.

HAPPY HOUR WITH THE PIRATES, Thursday 10th November – 5:30pm
Head to Margaritaville on the waterfront for the pre-Pirates Week Happy Hour where pirates and landlubbers alike can take advantage of Red Stripe and Bacardi specials.

It all begins at 5:30pm with the famous Margaritaville Happy Hour and since we are on “Cayman time” you can expect the occasion to be somewhat stretched, so expect a happy hour that goes until 9:00pm.


On Thursday 10th November, the sweet sounds of the steel pan will be ringing through the evening at the historical Pedro St. James great house. The location is dubbed the birthplace of democracy in the Cayman Islands with Bodden Town (the district where it is located) being the country’s first capital city.

The event, sponsored by Caribbean Utilities Company (CUC), hosts several steelbands representing schools island-wide competing to become the Steel Band of the Year. Senior bands will also showcase their talents in now anticipated annual musical event.

The instrument originated in Trinidad & Tobago but has swept the world with its unique and irresistible energy. These days it is not just calypso and soca; but pop, rock, classical, jazz, and even hip hop that benefit from the official sound of the Caribbean, the Steel Pan.

The steel band event this year will be held on holiday Thursday, 10 November at 6:00pm the event is open to all steel bands in the Cayman Islands.

PIRATE PARTY AT THE WHARF RESTAURANT, Thursday 10th November – 9:00pm
The Wharf ramps up for the annual Pirates Kick-Off Party. At this annual event you can share a meal and have a drink with local or visiting pirates.

As the excitement starts to truly build, listen to the sounds of the best local rhythms as you dance the night away.

PIRATES WEEK 5K WALK/RUN, Friday 11th November, 2016
Pirates Week 5k Run/Walk
Check-in 3:30 pm | run starts at 5:30pm
Harbour Drive (Bayshore Mall) sponsored by the Ministry of Sports, Island Supply, Bard Crudo , Guy Harvey’s and Harley Davidson Cayman Islands
Funds raised benefit the 345 Athletic Club
$25 registration fee (first 100 entries receive a t-shirt)
Register online at

Sponsored by the Ministry of Sports, the Pirates Week 5K Walk/Run is organised by the Pirates Week Office in conjunction with the 345 Athletic Youth Club.

Beginning at 5:30pm, the race starts and finishes on Harbour Drive.

Race day check-in will take place at Bayshore Mall from 3:30pm to 5:00pm which is in the immediate vicinity of the start/finish area. The first 100 runners will receive a free t-shirt. Spot prizes will be raffled off post event.

The race course takes athletes south from Harbour Drive onto South Church Street with the turnaround point at Webster Estates, returning to Harbour Drive.

WHO WILL BE FESTIVAL QUEEN? Friday, 11th November, Harbour Drive – 7:15pm
Every young lady dreams of being queen on a tropical island; which is why the Festival Queen contest is so very popular amongst Caymanians.

Sponsored by the Ministry of Culture, Miss Festival Queen is tailored to ladies 16 and older and is a unique way to showcase Caymanian culture through design.

This wholesome, family-friendly event is a competition between the district Heritage Committees. Each district elects a young lady as its representative and everyone works to together to design a costume.

This year’s Pirates Week Festival theme is “Age of Romance” and costumes will be judged on their design as it relates to that theme. Other areas of adjudication include authenticity, stage presentation, use of Caymanian products and design detail.

The winner lead the annual day parade, showing off her district’s winning costume to a crowd of more than 12,000 people. All contestants will showcase their costumes at their individual Heritage Day events

PRE-LANDING ENTERTAINMENT- 2:00pm to 3:00pm, Main stage and Harbour Drive
Tide Tricking
Tide Tricking is a team who perform Martial Arts Tricking. Martial Arts Tricking (known simply as “Tricking”) is a high energy sport that combines martial arts kicks with flips and twists from gymnastics as well as many dance moves and styles from break dancing.

Founded in January 2016 – Tide Tricking strives to promote a creative, active and healthy movement throughout the community. With members of all ages and nationalities Tide Tricking encourages a team mentality.

Since the formation of Tide Tricking they have performed at various events such as; the 2016 Cayman Islands Annual Agriculture Show, the 2016 Cayman Islands Fashion Week, the 2016 NORCECA Volleyball Championships, the 2016 ANBF Natural Caribbean Championships and recently travelled to Germany to compete in the High 2 gathering.

A performance on the water in Hog Sty BAy by Fat Fish and Cay Jet (jet boots).

Dance Unlimited
Since 1988 The Cayman Islands National Dance Company & School – Dance Unlimited, has offered the highest quality instruction in dance while making classes fun and enjoyable for students and adults.
Tonight they will be performing “Bring the Beat” by Machel Montano, choreographed by Melissa Mcfield.
Also gracing the stage with the company is reigning Miss Cayman Islands, Monyque Brooks who has been dancing with the company for a number of years. Enjoy their energy, style and grace.
Top BMX talent invades Grand Cayman
Four of the best BMX riders from around the world will be arriving to Grand Cayman this weekend to showcase their talents in multiple demonstrations.

Five time X Games Gold Medalist Daniel Dhers, two time NORA Ramp Rider of the year Drew Bezanzon, and young up and comer Kenneth Tencio, will be taking their talents to the Black Pearl Skate Park.

The demonstration will take place on Friday at TIME??? at Black Pearl Skate Park.
“I am super excited to ride Black Pearl and visit Grand Cayman. I have seen so many photos and cannot wait to ride it!” remarked Venezuelan Daniel Dhers.

Costa Rican Kenneth Tencio added, “In addition to riding the Skate Park, which I am super stoked to do, I want to see more of the island. Hopefully I get to check out the sting rays and hang out with the locals.”

BMX Flatland legend, Terry Adams, will be joining the crew and performing his tricks for the crowd Saturday afternoon on the Waterfront along Harbour Drive

All are welcomed to see the top BMX talent in the world!

See additional info/images below:
Terry Adams

Drew Bezanson

Kenneth Tencio

Daniel Dhers

LANDING AND PARADE BEGINS AT 3PM – Broadcast live to all three islands on Cayman 27 and Radio Cayman – Saturday 12th November

A young pirate and the direct heir to the Jolly Roger, Dominic Bellweather has fallen in love with a young noble woman, Hannah.

Hannah, the daughter of the recently deceased Governor of the Cayman Islands, tries desperately to keep the forbidden love affair a secret but their meetings have been discovered by her mother.

Now lacking her mother’s trust, she has been betrothed to a gentleman from abroad.
While awaiting her suitor’s arrival, Hannah is placed under the watchful eyes of the British guard; the Red Coats.

But the young woman yearns for her true love’s return and for him to take her away to a life of adventure on the seas.

Each year people line the streets to watch the spectacle and its all good-natured swashbuckling fun, it is anticipated that thousands will come out on Saturday 12th November to see how the story ends.

CHILDREN’S FUN DAY, Sunday 13th November -12:00pm to 4:00pm
This sun bathed fun filled day is what Pirates Week is all about. For more than two decades, the Children’s Fun Day is a celebration where the community comes together donating time and money to stage the event.

This year’s sponsors are CIBC First Caribbean International Bank, Popeye’s, and Burger King and Pedro St. James. The fun starts at 12:00pm on Sunday, 13 November and goes on until 4:00pm on the grounds of the historic Pedro St. James great house.

On arrival every child receives a goody bag and tickets for a free lunch and entry into a prize drawing for one of 6 bicycles. There will also be a bouncy castle, face painting, snow cones and cotton candy for little ones to enjoy!

And if you were wondering, yes, the pirates will be there to entertain the children with stories, songs and lovable antics!

Look out for the amazing Children’s Pirate Costume Competition featuring winners in two categories— Tiny Tots and juniors.

On the spot cash prizes will be awarded to all First Place and Runner-Up winners, to enter just turn up on the day at the Pedro St. James location in Bodden Town. The Children’s Pirate Costume Competition will take place at 2:00pm.

The event is judged on originality of costumes and “pirate attitude”—whether contestants tell pirate jokes, speak like a pirate or more—judges are looking for a fun pirate dressed character. Audience participation is encouraged.

CARDBOARD BOAT RACE – Saturday, 19 November
The annual Caybrew Cardboard Boat Race is a riotous occasion with thousands of spectators inciting daring lads and lasses in their quest to race around the bay. But there’s one catch, the crafts can only be made of cardboard, duck tape and glue! No engines and fiberglass allowed.

Only the people inside—dressed as everything from spacemen to Captain Birdseye and everything between—are allowed to power these homemade boats. This comically entertaining event first took place in 2007 as a fundraiser for playground equipment, the idea of Build Cayman. Needless to say, it was a huge hit and has been a central must-see at Pirates Week ever since.

With renewed sponsorship from organizers local brewery Caybrew and Kirk Freeport, funds raised from this event will go towards one of the many local charities, and a donation will be made to Pirates Week to help defray their costs.

The fun surrounding the Cardboard Boat Race begins at 2:30pm on Saturday, 19 November in the George Town Harbour (Harbour Drive). The race itself begins at 4:00pm.

Pirates Week is busy working to remove the stigma that it is an event only for revelers, but the main focus is on sharing our island paradise and our culture. Cayman Islands may be a mere speck in the vast Caribbean Sea but that in no way diminishes the islands long and proud history. The brave settlers had to develop unique and creative methods of construction, preparing meals, making clothes and shoes as well as creating crafts and music to make it through the centuries before the trappings of our present modern day civilization.

Heritage Days celebrate the talent and genius of our forbearers, keeping old skills alive and educating the current generation about this splendidly inventive past. Silver Thatch weaving for example is a unique island skill that has underpinned many of our receptacles, hats and other household and clothing items.

How about an old-time fish fry? It’s not just sticking a snapper on a barbecue – there’s a skill in setting the fire in a sand bottom caboose, selecting the correct temperature and cooking up those delicious sauces to accompany.

Perhaps you’re interested in Cayman’s musical tradition or hearing stories of the old times, an art in itself for sure. We can all obtain much deal from hearing and learning about our past and even more by giving it a go ourselves.

The Heritage Days run district by district, each putting on a very special day during which they showcase their skills, food, music and friendliness. It really is a treat to be able to connect with the past as well as catch up with old friends, all in Pirates Week’s legendary family-friendly atmosphere.

We may be a small trio of peaks here in the centre of the Caribbean, but we have hearts as big as the world and knowledge that has taken us o’er seas – and home again.

Little Cayman, 4 – 6 November, 2016

Monday 14th November
Bodden Town Heritage Day, Harry McCoy Park/Nurse Josie Senior Centre, Gun Square Ave sponsored by the Ministry of Tourism and Department of Tourism, 11:00 am – 5:00 pm

Bodden Town Music and Food Festival, Pedro St. James sponsored by the Ministry of Tourism and Department of Tourism, 6:00 pm – 11:00 pm

Tuesday 15th November
George Town Heritage Day, Farmers Market, Huldah Avenue sponsored by the Ministry of Tourism and Department of Tourism, 11:00 am – 11:00 pm

Wednesday 16th November
East End Heritage Day, Heritage Field sponsored by the Ministry of Tourism and Department of Tourism, 11:00 am – 2:00 am

Thursday 16th November
West Bay Heritage Day, West Bay Heritage Field sponsored by the Ministry of Tourism and Department of Tourism, 11:00 am – 2:00 am

Friday 18th November
North Side Heritage Day, Water Key Public Park (next to Kaibo Restaurant) sponsored by the Ministry of Tourism and Department of Tourism, 11:00 am – 2:00 am
Fireworks at 8:00 pm

Cayman Brac, 25 – 27 November, 2016

Back by popular demand after making its debut in 2015, crowds want to live the magical moment when the glow of thousands of colorful lights comes alive in the middle of the waterfront.

Come admire the biggest, brightest and most vibrant parade in the Cayman Islands at our annual ‘Illumination’ night parade. Watch as floats dance troops, acrobats, percussion bands are transformed with thousands of twinkling lights. Of course you can expect to see spectacle with those rowdy pirates!

The “Illumination” Parade takes place on Saturday, 19 November at 7:00pm on Harbour Drive and is followed by our spectacular fireworks finale. This is one event you do not want to miss.

ULTIMATE TEEN DANCE PARTY – TEEN UP STREET DANCE, Saturdays (12th and 19th November)
Sponsored by Pepsi, supported by Radio Cayman, the National Drug Council and the Youth 2 Youth Programme.

The Teen Up Street Dance takes place on the first and the last Saturday of Pirates Week (12th and 19th) and is located along Goring Ave, just off the Harbour Drive festival thoroughfare.

Sponsored by Pepsi this very popular event is an opportunity for teens to enjoy themselves in a safe environment while dancing the night away to the latest reggae, hip hop and soca music featuring the islands’ most popular DJs.

Goring Avenue is situated right in the midst of the activities. It’s close enough to the Street Dance for parents to pop in and keep an eye on things, but you’re not allowed in chaps, this is a teen zone only!

Entry is free and is open to teens between the ages of 13 to 17. Security officers supported by National Drug Council volunteers will keep watch over the enclosed dance floor providing a place for teens to enjoy the festival in a more age appropriate atmosphere where the music and the teens take center stage.

Monday, 14 November
7.30 am Grand Cayman Beach Suites
Sponsored by KPMG
Funds raised benefit the Cayman Islands Amateur Swimming Association (CIASA)
Registration fee CI$25/CI$30
Register online at

A tradition for 35 years, the Pirates Week Open Water 5K, sponsored by Pirates Week and KPMG is provisionally set for 7:30am on Monday 14th November 2016.

The swim starts and finishes at the Grand Cayman Beach Suites; registration takes place from 6:15-7am and the race begins promptly at 7:30am.

The entry fee for CIASA members is CI$25 and for non-CIASA members is CI$30.
The 5K open water swim is a challenging distance and members of the public are encouraged to come out, enjoy an early morning on the beach and support our swimmers – some of whom will be tackling this distance for the first time.
All swimmers are provided with swim caps, which must be worn for safety reasons and there are event T-Shirts, trophies for the top three male and female finishers in each age group and refreshments provided at the end of the race.

The Stingray Swim Club (SSC) and will be hosting The Mike Lockwood Memorial International Swim Meet from Thursday 10th to Sunday 13th November at the Lions Aquatic Centre, off Academy Way. As well as local swimmers and teams, there are regular visitors from further afield including Jamaica and the United States.

The pool competition memorialises the work of former Pirates Week Executive Director and swim parent, Michael Lockwood and begins on Thursday, 10th November at 3:00pm with more sessions on Friday evening, Saturday and Sunday mornings. It’s going to be competitive, fun and family-friendly for all ages. The youngsters also get an opportunity to capture some real pirate booty in the form of trophies, medals and ribbons. Meet entry forms are available from the Stingray Swim Club website (

The Stingray Swim Club comes under the umbrella of the Cayman Islands Amateur Swimming Association (CIASA). It was established in 1996 to develop competitive swimming amongst all groups. SSC arranges travel to overseas meets, promotes an incentive badge programme for its swimmers, holds FINA officiating clinics and organizes local pool meets.

Saturday 19th November, 2016
Check-in 8:30 am | Parade 9:00 am
Harbour Drive
Funds raised benefit the Cayman Islands Humane Society
$25 registration fee (first 50 entries receive a t-shirt)
Register online at

The now annual Pirate Pooch Parade will be hosted during the annual Pirates Week Festival in celebration of our furry four legged friends. This event was designed with a purpose of raising funds for the Cayman Islands Humane Society.

The Pirates Pooch Parade will take place on Harbour Drive on Saturday, November 19 at 9:00am. Check-in 8:30 am | Parade 9:00 am.
No charge for canines, but a $25.00 fee for pet parents includes a t-shirt! Register online at
All dogs must be leashed.

Pet parents and their pooches will be entered to win a round trip ticket on Cayman Airways in the Pooch Parade Facebook photo contest. The day after the parade, folks can help their favourite pooch and parent win a round trip ticket on Cayman Airways by voting on Facebook.

• Like the CaymanIslands Pirates Week Festival Facebook page and vote for your favourite pooch and the image with the most likes will win!
• Voting for the Pooch Parade Photo Competition will begin on Monday 21st November and closes on Wednesday 30th November.
• The winner will be notified on Thursday 1st December.

Sunday 20th November, 2016
Check-in 3:30 pm | run starts at 5:30pm
Raleigh Quay Rd. West Bay Road sponsored by the Ministry of Sports, Aquafina and Calico Jacks
Funds raised benefit the Pirates Week Festival
$25 registration fee (first 100 entries receive a t-shirt)
Register online at

A little more serious, the T Hell and Back 10K Run, sponsored by the Ministry of Sports, Aquafina and Calico Jacks attracts over 150 runners locally and internationally. The race starts at 7:00am on Sunday 20 November and registration will close at midnight on Wednesday 16th November.

Top male and female finishers in each age group receive awards. The entry fee includes a t-shirt and a chance to win prizes and surprises in our end of event raffle. NO RACE DAY REGISTRATION.

The race starts at Raleigh Quay Rd., West Bay Road (next to the Kimpton Seafire Hotel). The finish is at Calico Jack’s on the beach where everyone can assemble for a well-deserved breakfast.

Runners are advised to take precautions against dehydration. This race is also open to joggers, walkers, and baby carriages so you can make it a family affair if you wish. For more information call Pirates Week Office at 949-5078.

CAYMAN BRAC, 25-27th November
The festivities continue in Cayman Brac as we set our sights on the bluff and journey to that second largest of the sister islands to enjoy the Pirates Week celebrations.

Pirates Week on the Brac is all about having fun in a friendly atmosphere – children and the adults alike are drawn to paradise for the camaraderie, the sun and the excellent history of pirates, which continues to be held up as the flag ship event for tourism in the Caribbean.

On Friday 25th November through Sunday 27th November, land lubbers and scallywags can enjoy a pirate happy hour, BBQ’s, dances, fireworks a float parade, heritage displays and a family bon fire.

Inter-island service between Grand Cayman and Cayman Brac is provided by Cayman Airways.

Cayman Brac Schedule of events
Friday – Nov 25, 2016
Happy Hour, La Esperanza Watering Place, 3:00pm to 5:00pm
Pirates Party Kick-off Dance, La Esperanza Watering Place, 9:00 pm – 2:00 am

Saturday – Nov 26, 2016
Heritage Day Events, Heritage House sponsored by the Ministry of Tourism, 8:00 am – 2:00 pm
Float Parade, (starts at empty lot across from old Alexander Hotel), 4:00 pm -6:00 pm
Happy Hour and Finale Party, Cayman Brac Reef Resort, 6:00 pm – 11:45 pm
Illumination Boat Parade, Channel Wharf, 6:00pm

Sunday – Nov 27, 2016
Pirates Farewell Lunch, La Esperanza Watering Place, 11:00 am – 2:00 pm

Print Friendly, PDF & Email

Speak Your Mind