Council members will discuss proposals for the Orkney Islands to change its status in the UK or perhaps turn into a self-governing state of Norway.
The local authority will consider a motion on Tuesday to look into “alternative forms of governance”.
Orkney doesn’t receive equitable financing, according to council head James Stockan, given its present relationship with the UK.
However, a notion that the islands would sever its relations with the union was rebuffed by the prime minister’s office.
Mr Stockton has urged councillors to back his idea to find new ways to get greater financial security and economic opportunities for Orcadians.
Speaking on BBC Radio 4’s Today programme on Monday, he said: “The mark of a good government is how it actually supports the periphery and the most disadvantaged.
“Our communities on the tiniest of our islands are the most difficult to serve and the way governments treat them is absolutely paramount to how well governments are doing.
“We do look with envy at the communities in Norway where they have a completely different approach to the remote and rural.”
Orkney Islands Council previously voted in 2017 to look at whether the islands could have greater autonomy.
While they wanted to have a “stronger voice”, they did not back full independence for Orkney.
Mr Stockan’s motion also cites British Crown Dependencies Guernsey, Jersey and the Isle of Man as potential models to follow.
The council leader said among the issues being faced by islanders is an ageing ferry fleet.
He added the situation was “critical” because the ferries, which are older than the Western Isles fleet, were beginning to fail.
But despite Mr Stockan’s concerns, Downing Street dismissed the idea of Orkney breaking away from the UK.
‘The UK is stronger united’
Prime Minister Rishi Sunak’s official spokesperson said: “First and foremost there is no mechanism for the conferral of Crown Dependency or Overseas Territory status on any part of the UK.
“We have no plans to change the devolution settlement we are supporting Orkney with £50m to grow the economic prosperity of the Scottish islands, through the islands deal.
“But the Government’s position is that the UK is stronger united.”
Orkney was previously held under Norwegian and Danish control until it became part of Scotland in 1472.
The islands were used as security for the wedding dowry of Margaret of Denmark, the future wife of King James III of Scotland.
The Scottish government said in 2023-24 Orkney Islands Council would receive £89.7m to fund services, with an extra £4.6m from an increase in council tax by 10%.
A spokesperson added it was “committed to supporting island communities”.
The Norwegian government declined to comment on the proposals.