Author Guide · Political Philosophy & History
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In early 1513 Niccolò Machiavelli, who had served the Florentine republic for fourteen years as head of its Second Chancery, was imprisoned for twenty-two days and tortured with the strappado on suspicion of plotting against the newly returned Medici. Released in March, he retired to his family’s farm at Sant’Andrea in Percussina, south of Florence. By 10 December he could tell his friend Francesco Vettori that he had written “a little work” called De Principatibus. It became The Prince, printed in 1532, five years after his death, and it turned his surname into an adjective. Only one of his political or historical books, The Art of War, was printed while he was alive; the rest, including a long defence of republics and a bawdy comedy, followed later. This guide covers his seven key books, in order, and where to begin.
By Lisanne Swart · 7 key books · 1521–1549 · Updated October 2026
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Quick answer
Niccolò Machiavelli’s key books are The Prince (written 1513, published 1532), the Discourses on Livy (1531), The Art of War (1521), the Florentine Histories (1532) and the comedy The Mandrake (printed 1524). Start with The Prince: it is short, and almost everything said about him begins there. Then read the Discourses, which show a writer who, on balance, preferred republics.
Where to Start with Machiavelli
If you want the book everyone argues about
→ The Prince (1532) — 26 short chapters on how power is won and kept.
If you want his case for republics
→ Discourses on Livy (1531) — his longest work of political thought.
If you want to see that he was funny
→ The Mandrake (1524) — a comedy still staged five centuries on.
If you want history rather than theory
→ Florentine Histories (1532) — Florence from its origins to the Medici.
7 Niccolò Machiavelli Books, in Order
The Art of War (Dell’arte della guerra)
Written in 1519–1520 and printed in Florence in 1521, it was the only one of his political or historical works published in his lifetime. Set as a conversation in the Orti Oricellari, the Rucellai family gardens in Florence, it gives most of the talking to the mercenary captain Fabrizio Colonna, who argues for rebuilding armies on the Roman model. It went through twenty-one editions in the sixteenth century and was translated into French, English, German and Latin.
The Mandrake (La Mandragola)
A five-act comedy set in Florence in 1504 and played out in a single day. Callimaco wants Lucrezia, the young wife of the elderly lawyer Nicia; with the fixer Ligurio and the corrupt Friar Timoteo he poses as a doctor and sells Nicia a mandrake potion to cure the couple’s childlessness. Alberto Lattuada filmed it in 1965, and it has been turned into several operas.
Discourses on Livy (Discorsi sopra la prima deca di Tito Livio)
Written around 1517 as a commentary on the first ten books of Livy’s history of Rome, in three books and 142 chapters, dedicated to his friends Zanobi Buondelmonti and Cosimo Rucellai. It argues that republics are generally better than principalities, praises mixed government, and claims that the conflict between Rome’s nobles and people kept the republic free. It was published posthumously in 1531.
The Prince (Il Principe)
Written in 1513, in the months after his release from prison, under the working title De Principatibus (“Of Principalities”), and dedicated to Lorenzo de’ Medici in the hope of returning to office. In 26 short chapters it describes how principalities are acquired and held, and asks in chapter 17 whether it is better to be loved or feared. It was printed in 1532 with the permission of Pope Clement VII and put on the Index of Prohibited Books in 1559.
Florentine Histories (Istorie fiorentine)
Commissioned in 1520 by Cardinal Giulio de’ Medici, who had become Pope Clement VII by the time Machiavelli presented the work to him in 1526. In eight books it traces Florence from its origins to the death of Lorenzo the Magnificent in 1492, with set-piece accounts of the Ciompi revolt of 1378 and the Pazzi conspiracy of 1478. It was published in 1532.
The Life of Castruccio Castracani of Lucca
A short life of the fourteenth-century condottiere who ruled Lucca, probably written during Machiavelli’s visit to the city in 1520 and dedicated to Zanobi Buondelmonti and Luigi Alamanni. Machiavelli has Castruccio found as a baby abandoned in a field, and ends with a string of sayings that Leo Strauss showed were mostly borrowed from classical writers such as Diogenes Laërtius.
Belfagor (Belfagor arcidiavolo)
A comic novella in which Pluto, puzzled by how many men arrive in Hell blaming their wives, sends the devil Belfagor to Florence to find out. Disguised as Roderigo of Castile, he marries Onesta Donati, is ruined by her spending and her relatives, and goes back to Hell glad to be rid of marriage. A shortened version appeared in 1545; the full text was published in 1549.
In What Order to Read Machiavelli
Publication order is misleading with Machiavelli, because almost everything was printed after his death in 1527: The Prince (1513) and the Discourses (around 1517) were written years before The Art of War, yet printed a decade after it. Nothing is a sequel, so read by subject.
Most readers start with The Prince and then go straight to the Discourses, because the two books answer each other: one addresses a single ruler, the other a free republic. The Mandrake and Belfagor are short and can be read at any point.
A reading path
1. The Prince (1532)
2. Discourses on Livy (1531)
3. The Mandrake (1524)
4. The Art of War (1521)
5. Florentine Histories (1532)
Everything Else Niccolò Machiavelli Wrote
Beyond the 7 key books: 4 more, grouped by kind.
Open a group with the + to see every book in it.
Poems and plays
3
3 books · 1504–1525
- 1504Decennale primoa verse chronicle of Florentine events, written in 1504
- 1517L’Asinoan unfinished satirical poem, written around 1516–1517
- 1525Cliziaa comedy adapted from Plautus’s Casina, written and staged in 1525
Letters
1
1 book · 1513
- 1513Letter to Francesco Vettori10 December 1513, describing his days at Sant’Andrea and announcing De Principatibus
The years · 1469–1527
Quick facts about Niccolò Machiavelli
- Known for
- Machiavelli is known for arguing, in The Prince, that politics has its own rules apart from conventional morality, an idea that made “Machiavellian” a word for cunning and bad faith.
- 1469
- Born in Florence
- 1498
- Head of the Second Chancery
- 1502
- Two missions to Cesare Borgia
- 1513
- The Prince
- 1527
- Dies in Florence
- Born
- 3 May 1469, Florence, son of a lawyer
- Died
- 21 June 1527, Florence; buried in Santa Croce
- Office
- Head of the Second Chancery and secretary to the Ten, 1498–1512
- Missions
- To Louis XII of France, Cesare Borgia, the papal court and Emperor Maximilian I
- Married
- Marietta Corsini, 1501; four sons and two daughters
- Imprisoned
- Twenty-two days in early 1513, tortured with the strappado
- Banned
- His works were placed on the Index of Prohibited Books in 1559
The red mark is 1513: the year he wrote The Prince, months after his release from prison.
How Machiavelli Writes: Examples, Choices and Plain Advice
Machiavelli argues from examples. The Prince sets ancient cases beside ones he saw at first hand as a diplomat — Cesare Borgia, whom he visited twice in 1502, Louis XII, Pope Julius II — and draws a rule from each. The Discourses do the same at greater length, taking episodes from Livy’s Rome and asking what Florence should learn from them.
He likes to split a question into two options and choose one bluntly: whether it is better to be loved or feared, whether to trust fortune or prepare against it. The chapters are short, the sentences plain, and he states openly that he is describing how rulers actually behave, not how they ought to. That frankness, more than any single piece of advice, is what shocked his early readers.
He was also a dramatist and storyteller. The Mandrake applies the same cold eye to a Florentine household, where everyone gets what they want through deception, and the Florentine Histories follow the humanist custom of putting invented speeches in the mouths of real people, such as the wool-carder Michele di Lando during the Ciompi revolt of 1378.
Frequently asked questions about Niccolò Machiavelli’s books
How many books has Niccolò Machiavelli written?
Seven key works are listed on this page, from The Art of War (1521) to Belfagor (1549). He also wrote verse, including the Decennale primo and the unfinished L’Asino, a second comedy, Clizia, and many letters and official reports from his years in office.
What are Machiavelli’s books in order?
By first publication: The Art of War (1521), The Mandrake (1524), Discourses on Livy (1531), The Prince (1532), Florentine Histories (1532), The Life of Castruccio Castracani (1532) and Belfagor (1549). By date of writing, The Prince (1513) comes first.
Where should I start with Machiavelli?
With The Prince. It is short, it is the book his reputation rests on, and it makes the Discourses on Livy, the natural second book, easier to follow.
What is Machiavelli’s most famous book?
The Prince, written in 1513 and published in 1532. Its argument that a ruler must sometimes act against conventional morality to keep his state is the source of the word “Machiavellian”.
When was The Prince written and published?
He wrote it in 1513 at his farm at Sant’Andrea in Percussina, after his release from prison, and described it to Francesco Vettori in a letter of 10 December 1513. It circulated in manuscript and was printed in 1532, five years after his death, with the permission of Pope Clement VII.
Was The Prince banned?
Yes. Machiavelli’s works were placed on the Catholic Church’s Index of Prohibited Books in 1559, and both Catholic and Protestant writers condemned The Prince. Readers have argued ever since about whether it states his real views: Rousseau, for one, held that the Discourses and the Florentine Histories reflect them better.
Is Machiavelli’s Art of War the same as Sun Tzu’s?
No. Machiavelli’s The Art of War (1521) is a dialogue set in Florence about rebuilding armies on the Roman model; Sun Tzu’s is an ancient Chinese treatise. They share only the English title.
Did Machiavelli write fiction?
Yes. He wrote two comedies, The Mandrake and Clizia, the comic novella Belfagor, and satirical verse. The Mandrake is still staged and was filmed by Alberto Lattuada in 1965.
Why was Machiavelli imprisoned?
When the Medici returned to Florence in 1512 he lost his post, and in early 1513 he was accused of taking part in an anti-Medici conspiracy. He was held for twenty-two days and tortured with the strappado, then released in March 1513.
Footnotes
- Niccolò Machiavelli — Internet Encyclopedia of Philosophy
- Niccolò Machiavelli — Encyclopedia.com
- The Prince — Encyclopædia Britannica
- Discourses on Livy — Wikipedia
- The Art of War (Machiavelli) — Wikipedia
- The Mandrake — Wikipedia
Bibliography last verified 9 October 2026. Where sources give different first-publication years, this page uses the year in library catalogues or the publisher’s own record.
This list was not put together by a machine.
The notes are all mine,
and the books are all his.
Lisanne x
Written by Lisanne Swart, who has curated reading lists and author guides at lisanneswart.com since 2021.
See more on her personal bookshelf.
“It is much safer to be feared than loved, when, of the two, either must be dispensed with.”
— Niccolò Machiavelli, The Prince (1532), chapter XVII, translated by W. K. Marriott
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