For Jamaican comedian and social media personality Karlando “Bad Sekki” Bailey, the bright lights of New York City’s Times Square have long represented more than just a popular tourist attraction. They have been the setting for a video he has imagined creating for years, and come November, that dream could finally become a reality.

The popular content creator is now preparing for his first trip to the country, with plans to visit four cities, reconnect with family, and explore opportunities to further develop his craft.

But amid the excitement of travelling overseas for the first time, there is one particular moment Bailey is eagerly anticipating — standing in the heart of Times Square, surrounded by its towering digital billboards, and delivering a line he has long rehearsed in his mind.

“A just one video idea me have weh me really wah do from when, where I am in Time Square saying ‘New York’. That’s the main thing I am looking forward to,” Bailey shared.

The moment, although seemingly simple, carries considerable significance for the comedian, whose journey from working as a security guard to establishing himself as a popular Jamaican content creator has been marked by persistence, humour, and an ability to connect with audiences through everyday experiences.

His upcoming adventure, dubbed Bad Sekki Goes to America, will run from November 16 to December 2, 2026, documenting his experiences across four US cities while offering his followers a glimpse into a new chapter of his life.

For Bailey, the opportunity comes after a disappointing experience in March 2025, when his initial application for a US visa was denied. He subsequently shared the setback with his followers, generating encouragement from supporters who were eager to see him eventually realise his ambition.

Determined not to allow the rejection to derail his plans, Bailey reapplied in 2026 and was granted a visa in October.

“I felt happy and really thankful that I got it. I tried last year and didn’t get it,” he said, reflecting on the moment he received the good news.

According to Jason McNeish, who is spearheading the organisation of the trip, travelling to the United States has been one of Bailey’s long-standing aspirations.

“It has been a dream of his to travel and go to the US. He applied for his visa in 2025, which was denied. He reapplied in 2026 which was approved,” McNeish explained.

And while Bailey was ready to board a plane almost immediately after receiving his passport, McNeish said the team wanted to ensure that his first international experience would be memorable and beneficial to his career.

“He wanted to go the next day after he got the passport but we wanted to make it a whole trip. He will be visiting four cities so it took a longer time to plan,” he said.

The itinerary is being developed to combine entertainment, cultural exploration, family connections, and professional development, allowing Bailey to experience the United States both as a visitor and as a creative professional.

A major component of the trip will be content creation, with Bailey expected to document his experiences and share them with the audience that has supported his rise in Jamaica’s digital entertainment space.

New York, in particular, is expected to provide a backdrop for his signature brand of comedy, as he explores unfamiliar surroundings and captures the reactions and experiences that have become central to his appeal.

However, the trip will not be limited to sightseeing and social media videos.

McNeish revealed that plans are also being explored for Bailey to visit professional studios and gain exposure to international production environments, with the possibility of connecting with representatives associated with streaming giant Netflix.

“We are making it a full experience, he’s going to of course connect with family and more importantly for me he is going to get some professional development as well, so we are looking at visiting a few studios…” McNeish said.

He was careful to point out, however, that the proposed Netflix engagement has not been finalised. Discussions are ongoing with an agent affiliated with the company in the hope of arranging an opportunity during the visit.

The emphasis on professional development reflects an ambition to use the trip as a stepping stone towards expanding Bailey’s creative possibilities beyond the Jamaican market.

For the comedian, however, some of the most meaningful moments may come away from the cameras.

Among those eagerly anticipating his arrival is a cousin with whom he grew up, and who was one of the few people aware that he had decided to make another attempt at securing a visa.

“She was the first one I called. She was so happy for me because she was the only one I told that I was going to look about it,” Bailey recalled.

The planned reunion adds a personal dimension to an adventure that is already shaping up to be a significant milestone in his life.

The Bad Sekki Goes to America project will seek to capture those moments alongside the humour, excitement, and inevitable surprises of experiencing a new country for the first time.