Last year Andy Strangeway was the first man to ever land and sleep on all 162 of the islands off the coast of Scotland, a challenge which took him four years to complete.

This time he has set his sights on landing and sleeping on Rockall, a small isolated and uninhabited island in the North Atlantic.

Measuring 75ft by 90ft, it sits 300 miles from the coasts of Scotland, Ireland and Iceland.

Mr Strangeway, 42, said that more people have landed on the moon than have landed on Rockall from the sea. The crew of 10 people hope to achieve numerous firsts on the trip including the first American to land and the first person to swim around the rock.

But Mr Strangeway’s main aim is to be the first person to sleep on the rock without the assistance of a helicopter and without shelter. He also hopes to be the first Yorkshireman on the rock and has packed a flag to raise and have the first teddy bear to land. Teddy bear Clyde accompanied Mr Strangeway on all 162 of his island stays.

Mr Strangeway, a painter and decorator, said: “It’s very exciting. In recent years it has only been landed on in 2005/06 and nobody has slept a night on there without shelter. I’m living in hope that that’s what we are going to do.”

The team will get as close to the island as possible, on board a category O yacht, before jumping and attempting to land on Rockall.

He set off this week for the Outer Hebrides and the team will leave for Rockall on Monday.

He said: “It basically all depends on the weather. We need high pressure to come in for four to five days to bring the swell down. On a good day we would be jumping when swell is four to six foot. Forecast for next weekend is low pressure coming in, its totally in the laps of the gods, that could scupper everything.

“The highest ever recorded open waves in the world, 90ft, were recorded at Rockall. The island is 66ft high. We’ve covered all the variations and we’ve got the best crew we could have.”

Other passengers on the trip include Charles Veley, said to be the world’s most travelled man. He has visited 629 of the 673 countries, territories, island groups and provinces in the world. Mr Veley accompanied Ben Fogle in his unsuccessful attempt to land on Rockall in 2005.

The island is the most westerly point of Europe and is disputed territory between Denmark, Iceland, Ireland and the UK.

Mr Strangeway said: “When we get on we’ll claim it for Britain, we believe it’s ours. It’s the most difficult place in Europe to land, if not the world. It’s the ultimate place to get to. Everyone is asking what I’m doing next. There’s some fantastic islands out there, I’m looking into something else already.”