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.

The voyage continues with Timothy and Shane having to cope with the highly dangerous waters around Lizard Point if he is to complete the journey by winter. Although in a state of some anxiety, Timothy manoeuvres the Princess Matilda around the infamous Lizard before mooring in Newlyn, a focus of the Cornish fishing industry. But tying up for the night is never straightforward. The Spalls get advice from the eighteen-strong crew of the Penlee Lifeboat on how to tackle Land's End, another tough test lying in wait, and Timothy marvels at their seafaring skills and bravery in tackling the elements in order to save lives at sea. His own voyage attracts plenty of interest. 'They all think we're mad, but they're not stopping us!' laughs Tim at one point.

In the concluding leg, having navigated the Princess Matilda around the dangerous waters of Land's End and into the relative calm of the port of St Ives, Tim is still troubled. He now has to negotiate some of the most extreme tides in Britain as he plans his route through the Bristol Channel. Not only that, but it occurs to him that his anchor is faulty as he and Shane discover the delights of nearby Padstow, which attracts a million visitors a year for its seafood and other local attractions. From Padstow, Timothy and Shane moor overnight at Watchet in Somerset, but first have to navigate its notoriously difficult approach, and as they are behind schedule they have to cope with this in the dark. They eventually complete this task this with only a few bumps and bruises and then make it over to the Cardiff barrage and nearby Penarth Marina for the winter.