Philosophy Books to Take On Holiday

If you’re reading philosophy books this summer on the beach, by the pool, or in the garden, you don’t want something boring, but worthy; you don’t want something that’s too long to get through, or too big to fit in your bag. I’ve picked out five books I’d recommend for holiday reading that are all rewarding, readable, and stimulating, but not too heavy in any sense.

1. Socrates in Love by Armand D’Angour

Just published, Socrates in Love is a fascinating attempt to uncover the early life of Socrates, one of the greatest thinkers of all time. Whether you accept D’Angour’s theory that the young Socrates was very different from the older man portrayed by Plato – lover, warrior, wrestler, dancer – the elegance of D’Angour’s prose, and the lightness of his touch, make this a very pleasurable read. The author is an Oxford Classics don, so the erudition is there, but he takes the general reader along every step of the way. Could Socrates have had a female mentor who taught him the meaning of love? It is a radical thesis. And it could be true.

2. How to Live: Or, a life of Montaigne in one question and twenty attempts at an answer by Sarah Bakewell

Like Sarah Bakewell’s more recent book, At the Existentialist Café, this is beautifully written. How to Live is the story of the quirky 16th-century genius Montaigne, who was transformed by a narrow escape from death and by the early loss of a friend and became a reflective writer, retiring to his study to write brilliant and sometimes strange essays that can seem peculiarly modern. His digressive writing, often intimately confessional, playful, and challenging, all at the same time, is completely compelling. I challenge you to read Bakewell’s book without turning to the essays themselves. She gives their flavour and context, and discusses the best of them in a way that is both true to her subject, and is immensely satisfying to read.

3. The Complete Philosophy Files by Stephen Law

For those who are on holiday as a family, this is the ideal philosophy book to bring along. Written in short, humorous, easy-to-read chapters, with illustrations by Daniel Postgate, Law addresses most of the big philosophical questions, approaching them through imaginative sci-fi scenarios and thought experiments that are sure to get you discussing them. Is there a God? Should I eat meat? Where did the Universe come from? These are questions that children ask, and few adults can answer definitively. Once your children realise what you are reading, and how entertaining and stimulating this is, you’ll probably find them sneaking the book away to read themselves.

4. The Prince by Niccolò Machiavelli

If you want to get a perspective on how the politics of power and ruthlessness work, or simply see some of the thinking behind Game of Thrones, this short, slightly fragmentary book, written in the 16th century, is still the best around. Machiavelli, after a successful career as a diplomat in Florence, was tortured and exiled by the Medici after they came to power in the city state. He wrote The Prince from his exile, possibly as a way of gaining favour with those who could bring him back to Florence. So extreme is Machiavelli’s willingness to recommend any means whatsoever to gain and retain power, that many have read this book as ironic. I think he was probably serious: if you want your city state to survive, you’d better be ruthless at times, and it isn’t safe to be honest and fair. The Prince is full of pragmatic wisdom on such issues as whether it is better to be loved or feared (both if possible, but if you have to choose, be feared), how much luck is involved in human affairs (quite a lot, but you can prepare yourself in ways that make you more likely to succeed), and the animals a wise leader should emulate (the fox and the lion, rather than the lamb).

5. The Path by Matthew Puett and Christine Gross-Loh

In one way or another, the previous four books I’ve chosen are all concerned with the fundamental question of how we should live. This fifth book follows the trend, but from a different perspective. Based on Michael Puett’s incredibly popular lecture courses on Chinese Philosophy at Harvard University, it provides a way into the ideas of a number of the great Chinese philosophers, including Confucius, Mencius, Laozi, Zhuangzi, and Xunzi. This makes it sound a tougher read than it is. In fact, this book is both entertaining and challenging at the same time – challenging, not because the prose is difficult or the thinking hard to follow, but because the perspectives on ethics, which are frequently communicated through stories or thought experiments, are so different from the usual fare of Western philosophy.