For a story about going unprepaired try
A Bike Ride: 12,000 Miles Around the World
Ann Mustoe, 1992
Head of an upmarket private girls school, retires, buys a bike, starts a series of very long rides. In this volume, its her first ever ride. Starts off for the ferry with no practise and when she gets to Italy, casually mentions that she had to find a bike shop as she was wondering if it was time for someone to pump up her tyres. To paraphrase some of her other attitudes:
Crosses a large desert people have died in 'no need to take water, someone always passes and offers you some'.
Never learns to fix a puncture 'Its better to employ a local to do it as it gives them money. Someone on a truck always turns up however empty the landscape and you can get a lift from them'
Interesting read, foolhardy woman, cant believe she was ever trusted to head a school or teach kids as she had not a shred of sense. Died last year still biking. Luck of the devil to make up for the lack of intelligence!