The island’s under-19 schools football team set off from Ronaldsway for New York on Wednesday morning.
The squad have traditionally made the trip to America every summer since the first trip in 1997, usually to California.
However, there has not been a tour since 2019 because of a combination of the Covid-19 pandemic and restrictions placed on teaching staff during industrial action.
The squad of 18 players and four staff will be in New York for one week where they will play in the prestigious New York City Cup.
The squad will play three group games over Friday and Saturday with the aim of making it into Sunday's final.
The islanders also have a friendly lined up on Monday against a local team in Queens.
Teacher Matty Kelly, who is one of the staff that have travelled with the squad, added: ‘We would like to thank everyone involved in the trials process who helped select the squad, as well as Island Business Travel and MSN Roofing and Scaffolding for their generous sponsorship.’