The first programme sees Timothy and Shane set off in the Princess Matilda from Fowey in Cornwall, heading towards Land's End. By his own admission, Timothy is an unqualified and slightly nervous mariner, but Shane has every confidence in his seafaring abilities. The intrepid crew encounter a battleship on what could be a firing range, before getting holed up in the Helford river due to bad weather, which gives them an excuse to meet the locals and witness a lively festival. But all the time Timothy is fretting over the next leg of his journey, which sees the Princess Matilda circumnavigate the infamous Lizard Point, known as the graveyard of ships with its dangerous rocks stretching four miles out to sea.
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