Fife sailor survives two Caribbean shipwrecks in a week

A Fife sailor ended up battling for survival twice in one week, after being involved in two different shipwrecks.
Alan Hobbett had a very unlucky run.Alan Hobbett had a very unlucky run.
Alan Hobbett had a very unlucky run.

Alan Hobbett (56), from Burntisland, travelled to Trinidad for the trip of a lifetime, which involved sailing a yacht from the Caribbean to Portugal.

But things quickly turned sour after the SY Freedom was damaged by heavy seas and, after being dragged at the mercy of the weather, she was in danger of being boarded by pirates.

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After being rescued and taken back to dry land, Alan quickly found himself in another life-threatening situation when a storm damaged the next boat he boarded.

Alan Hobbett up the SY Freedom's mast.Alan Hobbett up the SY Freedom's mast.
Alan Hobbett up the SY Freedom's mast.

Following another dangerous ordeal, Alan made it back home safe, but told the Press that it hadn’t quelled his love of the sea.

“It wan’t quite what I expected, but an adventure all the same,” he said.

“There was a message on the Burntisland Sailing Club asking if anyone was interested in helpoing to sail the boat back from Trinidad to Portugal.

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“I flew over, met the skipper and travelled down to the harbour, but it had been left on a mooring rather than being taken out in the water.

Billy Wray aboard the Santa Rita.Billy Wray aboard the Santa Rita.
Billy Wray aboard the Santa Rita.

“It had been swinging on the mooring for about nine months so it took a lot of work – about three weeks to get it into condition where it could sail – but there were bigger problems than we realised.”

After the crew set off they found themselves in rough seas, taking on water, with a broken gearbox and the loss of the foresail.

And the crew were concerned by reports of several boats being boarded by armed pirates in the sea nearby.

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Alan said: “We’d been sailing for about six or seven hours; we were quite far out.

The Santa RitaThe Santa Rita
The Santa Rita

“We were drifting towards Venezuela and if we’d gone into Venezuelan waters the Trinidad Coastguard wouldn’t have picked us up because they’re a military force.

“We didn’t know what would have happened then.

“We certainly wouldn’t get the boat back, but folk said that if you do get back then you’d be wearing just your underpants.

“They sent a tug from Tobago, which was quite a while away and the seas had got really big by then.

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“It was pretty hard work, but the seamanship of the tug master was incredible, to control his vessel in really rough weather.

“It didn’t help that all of us were seasick because the conditions were so bad.

“We were very lucky. We actually drifted into Venezuelan waters but the current took us back again, and the coastguard were very good.

“When we got back they gave us a medical and breakfast. They were just really nice folk.”

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With the journey unable to continue, Alan looked to get himself home. This was when he met Billy Wray, a 78-year-old US Navy veteran who had spent all his working life at sea.

“We were on passage from Trinidad to Miami, where Billy was due to attend the US Veterans Hospital for treatment.” said Alan.

“The weather deteriorated very badly and 33 miles west of Grenada, at 2 o’clock in the morning, we were caught in a very severe storm which brought down the main mast and sails.

“When the mast came down, into the water, the current moves one way and against the wind so it was tipping the boat up at an alarming angle and we were in danger of capsizing.

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“The boat was listing badly and the situation was life- threatening.

“When you’ve got no power, and no sail and you’re drifting, the boat turns length-ways into the weather and you’re quite vulnerable then as you’re battered by the waves.”

Under Billy’s direction it took both him and Alan three hours to clear the wreckage.

With Billy at the helm, they reached safety in Grenada 13 hours later.  

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“In that storm Billy saved our skins and without him I’m not sure I’d be here now.” said Alan.

“Billy put out a mayday and there was a big Russian freighter which stood off, which means they hung about an hour or so in case we capsized so they would be able to lift us out of the water.

“For a while there it really was quite worrying.

“I was sick as a dog s it was so rough, but still trying to work through it all.

“We couldn’t start the engine on the boat until we’d got everything clear. If you catch a rope or wire in your propeller then you’re completely knackered.

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“We cut everything – the sail, the mast – and the boat righted itself a bit.

“We then headed to Grenada, but in that part of the sea there’s an area southwest of Grenada you try to avoid because it’s very rough.

“We just had to get in but even though it took us 13 hours to cross. It was a very lumpy journey; when you don’t have the mast it becomes much less stable.

“If we’d capsized in those first two hours before the freighter was there, I don’t know where we’d be.”

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Alan has now launched a fundraising campaign to help get Billy’s boat repaired.

He explained:“As the boat is Billy’s home, and given he simply doesn’t have the money to pay for the repairs, this becomes a personal tragedy for him and his family.

“Thanks to Billy’s expert seamanship, I’m safely back at home, but he is literally high and dry, living now on his damaged boat which is sitting out of the water awaiting repair.

“Without the money though, there will be no repair.

“I’ve never met a man quite like him.

“At 78 he’s as fit as I am, and I’m over 20 years younger.

“He’s also a far, far better sailor than I will ever be. He’s also stoic and has lived through very many challenges that most of us will never have to face, but this has really floored him.” 

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As for Alan, if the opportunity came up to finish the journey and get the SY Freedom from Trinidad to Portugal came up again, would he go back?

“I would,” he added. “When I got off the second boat I thought I’d never get on a sailing boat again and almost gave away all my sailing gear.

“But I realised that would be a bad idea.

“Maybe now, sitting by the warm fire in the house looking at the sea, I would go and finish it off if I could.”

If you would like to find out more about the fundraising campaign for Billy Wray, visit

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