Holland combined his teaching and medical practice with the translation of classical and contemporary works. His first published translation,
The Romane Historie (1600), was the first complete rendering of
Livy's
Latin history of Rome,
Ab Urbe Condita, into English. According to John Considine: It was a work of great importance, presented in a grand
folio volume of 1458 pages, and dedicated to the
Queen. The translation set out to be lucid and unpretentious, and achieved its aim with marked success. It is accurate, and often lively, and although it does not attempt to imitate the terseness of Latin, it avoids prolixity. As part of his book Holland translated two other substantial works –
an ancient epitome of Roman history which provides an outline of the lost books of Livy, and
Bartolomeo Marliani's guide to the
topography of Rome – as well as some smaller texts. These were taken from the edition of Livy published in Paris in 1573; by translating them, Holland was making available in English a great learned
compendium of historical knowledge, not simply a single ancient author. Considine says of it: This encyclopaedia of ancient knowledge about the natural world had already had a great indirect influence in England, as elsewhere in Europe, but had not been translated into English before, and would not be again for 250 years. Indeed, after four centuries, Holland is still the only translator of this work to attempt to evoke its literary richness and beauty. In 1603 Holland published
The Philosophie, commonly called, the Morals, dedicating it to
King James. Holland is said to have claimed that he wrote out the whole of his translation of the
Moralia with a single quill, which was later preserved by Lady Harington: In 1609 he published his translation of the surviving books of
Ammianus Marcellinus's history of the Roman Empire in the later 4th century AD, dedicating it to the mayor and aldermen of Coventry. The Corporation paid £4 towards the publication. In 1610 Holland translated the 1607 edition of
William Camden's
Britannia into English. Although he appears to have been solely responsible for the translation, the work was expanded with a certain amount of new material supplied by Camden. One of the printer-publishers of the volume was John Norton, to whom Holland's son,
Henry, had been apprenticed, and it was probably Henry who recruited his father to the project. Philemon in turn found a patron in
Elizabeth, Lady Berkeley, whose son,
George, he would later tutor: she appears to have offered £20 towards the publication, and considered doubling this to £40. However, when the first printed pages were circulated, it was reported that Camden "misliketh it & thinketh he [i. e. Holland] hath don him wrong", and Lady Berkeley may have reconsidered her support: her patronage is not mentioned in the published volume. At the last minute, Coventry Corporation contributed £5 towards the publication. adding to Thomas's original some 6000 words and meanings culled from the works of both ancient and modern Latin authors. In the following year he published
Theatrum Imperii Magnae Britanniae, a translation from English into Latin of
Speed's
The Theatre of the Empire of Great Britaine. In 1617 he translated the
Regimen Sanitatis Salerni, publishing it together with
Thomas Paynell's earlier translation of
Arnaldus de Villa Nova's commentary on the
Regimen. Holland also translated
Xenophon's Cyropaedia, completing a first draft in 1621, and continuing to work on it for the ensuing decade. It was published in 1632, prefaced by his portrait and a dedication to
Charles I by Holland's son, the printer
Henry Holland. The volume included a reprint of a poem on the
Battle of Lepanto by another son, the poet
Abraham Holland, and a description by Henry Holland of his father's
signet ring. ==Translation style==