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Leo Goolden departs Panama singlehanded aboard Taliho, bound for southeastern Cuba with a cargo of food and medical supplies destined for a local Cuban charity serving communities hit hardest by the humanitarian crisis and still recovering from last year's hurricane.▶ 0:12 The planned route heads east first to gain a better wind angle, then north across the Caribbean Sea.▶ 0:12 Goolden identifies three layered risks: the physical demands of a singlehanded Caribbean crossing during strong trade-wind season, including sleep management and weather routing; a security risk in the Caribbean; and the highest-probability risk — being denied entry to Cuba or refused permission to offload the supplies, given the difficulty of reaching Cuban government officials.▶ 2:34 The brown boxes stacked aboard are medical supplies sourced from a charity-provided list; food and other goods are stowed beneath.▶ 4:08 Goolden chose not to crowdfund the supplies, citing uncertainty about actually clearing Cuban customs and a personal preference to do the work first.▶ 4:22 Securing the loose cargo before departure is the immediate practical problem he faces before leaving.▶ 5:34

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