Caymanian Musicians Play Second Fiddle to International Stars at Pirates Week 2026

8 min read
Aerial view of crowds along the George Town waterfront and harbour with a pirate ship arriving during Pirates Week
Crowds line the George Town waterfront as a pirate ship sails in for a previous Pirates Week landing — Photo: Courtesy of CIFA

Editorial Note: The Caymanian Journal (TCJ) is an affiliate of Stingray Media Group, which operates radio stations in the Cayman Islands. This article refers to airplay on local radio stations.

Caymanian musicians say they have been left off most of the Pirates Week 2026 programme, which opened on Cayman Brac on 30 October with 15 visiting performers promoted and two local acts confirmed, according to the performers TCJ interviewed.

The national festival, in its 49th year according to its website, runs on Grand Cayman from 6 to 14 November, with Pirates Landing in George Town listed for 7 November, and closes on Little Cayman on 20 and 21 November. The festival's official promotions list 15 visiting performers and bands, including Destra, Rupee and Alison Hinds, each of whom has performed at the festival before, and Lyrikal, Nadia Batson, Skinny Fabulous, Farmer Nappy and DJ Puffy.

Six Caymanian performers told TCJ that the festival, which falls under the Ministry of Youth, Sports, Culture and Heritage, once built its live music around local bands and no longer does. The Ministry and the Pirates Week Office have been asked how many local acts are booked for 2026, how performers are selected and paid, and whether the song competition announced in July is running. In a Ministry release of 28 October, Minister Isaac Rankine MP said the festival brings "our community together across all three islands while creating opportunities to showcase our heritage, local talent and traditions".

A new song, and no airplay at home

Shane Allenger released a Pirates Week song, "Raise the Black Flag", ahead of this year's festival. He told TCJ that it is being played in Europe and elsewhere, and that the local radio stations he sent it to had not played it. Nobody commissioned the song, he said; he wrote and produced it himself.

Mr Allenger said local performers are undervalued, and that the change is most visible during Pirates Week. "It was our festival, but it's not that way any more. We've lost that symbiotic vibe, with everyone coming together. I don't think our children will ever experience that camaraderie," he told TCJ. "People should be coming out to hear us perform as the main acts, the same as when we went to hear the bands when I was young."

He recalled the Pirates Week Song Competition of earlier years. "The preliminary rounds held at the Lions Centre were a big deal, and the finals, held at the Agriculture Grounds, was like a rock concert. There's so much we're missing out on now, compared to what we used to have," he said.

The Cayman Islands Government said in a release on 27 July 2026 that "festival favourites and opportunities for public participation will return, including the Pirates Week song competition, t-shirt competition and the highly anticipated night parade". The festival's events page, which listed 26 of its 40 entries when TCJ read it on 3 November, carried no date for a song competition. The Office has been asked whether the 2026 competition is running and when it last took place.

The duo that last played the festival in 1995

Mr Shane Allenger is half of Hi Tide, a duo with Sean Hennings on guitar and Mr Allenger on conga drums, which plays hotel lobbies and restaurants. Both said they began in local bands decades ago and last performed at Pirates Week in 1995. They told TCJ they discussed forming a band for this year's festival but decided the cost and rehearsal time for a short-term event were prohibitive, and that while they do not play the soca and reggae that festival crowds favour, there is an audience for their style within the programme.

"Things won't change unless we can change the local music scene to what it used to be. When Cayman bands used to hit the stage, everyone was there," Mr Hennings said. He showed TCJ photographs on his phone of their band at the 1995 Pirates Landing, with what he estimated was 5,000 to 10,000 people in front of the bandstand.

The two said local bands were told in the 1970s and 1980s to modernise their sound for the tourism market, and did. Hi Tide now plays a mix of original and cover songs with a reggae and jazz-fusion style, has a following among repeat visitors, and has built its own recording studio. "Stayover tourism is where it's at for us now. We work with the hotels, restaurants and even taxi drivers," Mr Hennings said. He recently released a solo EP, and the duo have released several albums over the decades.

Other local acts

There are other local performers working in reggae, soca, rock, country and flamenco, among them Dario Ebanks, Nathan Barnett, Love Culture, Ratskyn and Neverines, who can be found through gig calendars and regular bookings along Seven Mile Beach.

"I always perform with pride," Mr Ebanks, a rock musician, told TCJ. "I've had some opportunities, but I haven't played Pirates Week for nine years, and I haven't heard a word this year. Even so, I 100% would welcome the opportunity to perform in front of my people."

Stuart Wilson, who performs solo and has worked on the local scene for more than 20 years, said he no longer relies on local audiences. "I don't rely on locals any more. Something has killed our spirit for each other, our music and for the finer things in life," he told TCJ. Of the festival he said: "Consecutive Pirates Week committees have done a disservice to local performers. I've been hired in the past, but it's never enough. We need to exist as well." He added that the best opportunities appeared to be reserved for others. "There's no incentive for us to be our best. That's the travesty," he said.

Mr Wilson holds a day job and plays between 12 and 25 evening gigs a month in the high season, he said. Local musicians are also hired to greet visitors at the cruise port and at tourist attractions under a government programme, the performers said. Mr Wilson and Mr Hennings said hospitality businesses find a solo musician, karaoke act or a DJ easier to afford than a band.

Two local acts confirmed

Vasti Bodden, the singer with the band Heat, performed at the Cayman Brac opening on 31 October and is to perform at Pirates Landing on 7 November. She and The Barefoot Man are the only local performers confirmed for the festival, according to the musicians TCJ interviewed. Ms Bodden has performed for 25 years and joined Heat, which she described as an offshoot of the Tradewinds, in 1999. She said two former Tradewinds players performed with her at the launch on Cayman Brac.

Brent McLean, who manages bookings for Heat and other groups and was overseas when TCJ spoke to him, said he had not been approached about performing at the pirates festival.

Ms Bodden's song "Proudly Caymanian", recorded two years ago, has brought her airplay, bookings and official appearances, she said, and CI$50 in earnings so far. The song features Sam Rose of Swanky Kitchen Band and was produced by Jason "Skorch Bun It" Gilbert, a Grammy-winning producer, a soca writer and a performer whose releases include "For the Love" and "Trouble on the Road". The Cayman musicians also named others like Andrea Rivera as performers who could have been booked this year.

The association that once vetted visiting acts

The Cayman Music and Entertainment Association (CMEA) is a registered non-profit organisation that, according to its former president Jean-Eric "Notch" Smith, once worked with the government and the Immigration Department on the work permits of visiting artistes.

Mr Smith, who told TCJ that the association is an advocate rather than a booking agency, said that the Pirate Week's first director, the late Chief Pirate Mike Lockwood, created the festival with the Tourism Ministry and Department.

Visiting Pirates Week bands were paid between CI$5,000 and CI$15,000 plus expenses, he said.

In comparison, local musicians were paid CI$100 an hour per performer, a rate he said had fallen to CI$50 before the Covid-19 pandemic. The government allocated CI$8,000 a year to the association for Pirates Week until 2000, the last year of that arrangement, he said. At other commercial venues, businesses were offered CI$200 a gig year-round, simply to encourage live bookings.

In earlier years, he said, local musicians were contacted for the pirate gala from September and began to prepare; this year few have been approached. "We were the checks and balances, and the visiting acts depended on endorsement by CMEA and a contract," he continued. He said no international act should visit without the association's involvement.

"None of the new hotels have venues for live music and don't cater to locals, so we're outside most economic opportunities, and relegated away from the Seven Mile Beach tourism corridor," Mr Smith said. The Cayman Islands Tourism Association has been asked to respond.

The CMEA's leadership has been in dispute since at least January 2020, when a public notice signed by Mr Smith as president declared a meeting of 12 January 2020 that purported to elect new officers "null and void" and called an annual general meeting for 1 March 2020. TCJ has also sought comment from Steve Errol Reid, who has held the presidency since a 2022 musician members' vote whose validity Mr Smith disputes. Mr Smith said differences remain and that the association's annual general meeting in March 2027 would settle its direction.

Both Smith and Reid are well-known local performers.

The Ministry's answers on how the 2026 Pirates Week lineup was chosen, what local and visiting acts are paid and whether the song competition is running, will be reported when received.

Published November 6, 2026, 5:19 PM

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