Now into its fourth year, the Sandals Foundation Island Challenge has expanded from Antigua to several other Caribbean destinations, with Thompson and his team at Sandals and Beaches Resorts' UK representative Unique Vacations raising more than £300,000 for the cause over the past three years.
Funds raised to date have helped provide local hospitals with vital medical equipment, supporting healthcare teams in delivering lifesaving treatment to babies and young children.
Thompson, who is Unique Vacations' UK Managing Director, is also UK director of the Sandals Foundation, the work of which inspired him to set up the Island Challenge and take on the challenges himself each year.
Over the first three editions, he has run more than 187km, kayaked 21km across the ocean, climbed 2,619 feet to the summit of Gros Piton in Saint Lucia and scaled La Soufriere, an active volcano in Saint Vincent and the Grenadines.
The 2026 challenge, which will be held in Jamaica, will see Thompson join 30 other participants for four days of endurance events over 2-5 October.
The challenge will begin with a 10km run through local communities followed by a 10km coastal kayak. Participants will then climb the 55-metre-high, 183-metre-long Dunn's River Falls before completing an 8km forest trek and jungle zip-line.
Day three will see the group take on a 21km half marathon through the 18th-century Georgian-style town of Falmouth, before the final day combines a military endurance challenge with a hike into the Blue Mountains, reaching an elevation of 4,500 feet.
All funds raised during the Jamaica challenge will support paediatric healthcare teams at hospitals along the island's northern corridor.
Thompson said: "This Island Challenge is especially meaningful as we continue to support Jamaica and celebrate the incredible strength and resilience of its people. We're doing this to raise funds, inspire hope and make a lasting difference for families across the island."