ORKNEY council is to consider proposals to change the island's status within the UK or even become a self-governing territory of Norway.
A motion will go before the local authority next week to investigate "alternative forms of governance".
James Stockan, Orkney council leader, said the island does not get fair funding within its current relationship with the UK.
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The independent Stromness and South Isles councillor has said he wants to look at Crown Dependencies, such as the Channel Islands and overseas territories like the Falkland Islands.
Stockan also suggested another possible future for Orkney could be in the same vein as the Faroe Islands, a self-governing territory of Denmark.
He told BBC Radio Scotland that there were areas where Orkney was being "failed dreadfully" by both the UK and Scottish Governments.
"We are really struggling at the moment, we have to replace the whole ferry fleet which is older than the CalMac fleet," Stockan (pictured below) said.
"We are denied the things that other areas get like RET (Road Equivalent Tariff) for ferry fares.
"And the funding we get from the Scottish government is significantly less per head than Shetland and the Western Isles to run the same services - we can't go on as we are."
The council leader added that an in-depth study of financial arrangements for the island has never been carried out.
"We know that we have contributed for the last 40 years through north sea oil, and the dividend we get back isn't sufficient to keep us going," Stockan added.
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"We've got a unique opportunity right at the heart of all the wind projects round our waters."
Stockan is urging fellow members of the local authority to back his idea and find new ways for the island to have greater financial security and better economic opportunities for Orcadians.
In 2017, Orkney Islands Council previously voted to look at whether the islands could have greater autonomy, but while they wanted to have a "stronger voice", councillors did not back full independence for Orkney.
British Crown Dependencies Guernsey (pictured below), Jersey and the Isle of Man are cited in Stockan's motion as potential models to follow.
However, he added that it would require a huge amount of staff resources to investigate the different options and undertake a public consultation.
"The council will decide whether it supports this motion and from there we will take our time, because we don't want to do this emotionally," he said.
"We want to look at all the practical implications and then we'll evaluate the results.
"We are looking for the very best position for future generations and our place in the world.
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Stockan also suggested that the council could secure a "Nordic connection" with Demark, Norway or Iceland.
Previously, Orkney was held under Norwegian and Danish control until 1472 when it became part of Scotland.
The islands were used as security for the future wife of King James III of Scotland, Margaret of Denmark.
"We were part of the Norse kingdom for much longer than we were part of the United Kingdom.
"On the street in Orkney people come up and say to me when are we going to pay back the dowry, when are we going back to Norway,
"There is a hug affinity and a huge deep cultural relationship there. This is exactly the moment to explore what is possible."
Orkney Island's Council will debate the motion on Tuesday 4 July.
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