
He’s run marathons, climbed mountains and raised millions of dollars for charity and yet veteran adventurer Derek Haines is showing no sign of stopping.
A former police chief superintendent, Haines, 77, is planning to trek 250 miles in Italy between Tuscany and Rome to raise vital funds for a new premises for Cayman Islands Meals on Wheels.
Last year, Haines completed the 175-mile Robert Louis Stevenson Trail in France with his nephew Tom Carlin, raising over $800,000 towards the new building, with groundbreaking taking place in June this year. However, to complete the construction and the fit-out, another $500,000 is required, so Haines is once more donning his walking boots.
Historic trail
The 28-day trek, which Haines is undertaking with friend and former rugby mate Greg Swart, takes in part of the epic trail walked by Hannibal and his elephants in 218 BC and includes total ascents of 23,478 feet.
“I’m feeling excited about getting back on the road again,” said Haines, who had originally considered a much longer 1,200-mile trek. (His wife Helen’s response to that suggestion was, “We need to talk.”)
“I know I can do the distance, which shouldn’t be as difficult as other ones I’ve done,” said Haines. “The main challenge is the fundraising.”

As with previous efforts, all travel costs, fees and accommodation will be self-funded by the two trekkers and every dollar raised will go directly into supporting the project. And once again, the Rotary Club of Grand Cayman will ‘ring fence’ the funds raised ensuring that supporters’ donations go straight to the very worthwhile cause.
Over the years Haines has hiked, climbed and run hundreds of miles to raise several millions of dollars for previous good causes, including the construction of the Jasmine hospice and palliative care building, the Jubilate after-school programme that teaches less-advantaged children from the public schools in the eastern districts various life skills, and Inclusion Cayman, previously known as the Special Needs Foundation Cayman, which Haines supported by doing a 550-mile hike across the Pyrenees.
Cayman community
“I have been a volunteer driver for Meals on Wheels for 26 years. It isn’t just the food that the volunteers deliver, it is human contact for our senior citizens who enjoy the social interaction. I believe it gives a vital service to our ageing citizens and gives extra quality to their lives. This represents another huge fundraiser, but the generosity of the Cayman community has shone through year after year and I am incredibly grateful for the continued support,” said Haines.

As patron of Meals on Wheels, Governor Jane Owen is fully supportive of this latest challenge to raise funds, said Haines.
Meals on Wheels was started in the Cayman Islands by the Rotary Club of Grand Cayman and provides free, hot, nutritious meals to over 350 seniors as well as homebound and disabled people across Grand Cayman every day, totalling almost 88,000 meals per year.

The charity has had to move its operational location many times but once the new facility is built, it will have a permanent base which will contains a kitchen, administrative offices, a pantry for supplementary groceries, a multipurpose room for community outreach and recreational use, and a vegetable garden. The new facility is expected to open in the first few months of 2026.
Haines is already getting stuck into his training regime which involves clocking up the miles before sunrise and is raring to raise as much as possible for the new premises.
“Let’s get this done,” he says. “And everyone, please be generous.”
Donations can be made directly to Cayman Islands Meals on Wheels at www.pledgeasenior.com.

