He was born in Gloucester, 24 August 1578. After his waterman apprenticeship he served (1596) in Essex's fleet, and was present at Flores in 1597 and at the siege of Cadiz.

He spent much of his life as a Thames waterman, a member of the guild of boatmen that ferried passengers across the River Thames in London, in the days when the London Bridge was the only passage between the banks. He became a member of the ruling oligarchy of the guild, serving as its clerk; it is mainly through his writings that history is familiar with the watermen's disputes of 1641 – 42, in which an attempt was made to democratize the leadership of the Company. He details the uprisings in the pamphlets Iohn Taylors Manifestation ... and To the Right Honorable Assembly ... (Commons Petition), and in John Taylors Last Voyage and Adventure of 1641.

Taylor discusses the watermen's disputes with the theater companies (who moved the theaters from the south bank to the north in 1612, depriving the ferries of traffic) in The True Cause of the Watermen's Suit Concerning Players (written in 1613 or 1614). He also addresses the coachmen, in his tracts An Errant Thief (1622) and The World Runnes on Wheeles (1623).

Taylor was also the first poet to mention the deaths of William Shakespeare and Francis Beaumont in print, in his 1620 poem, "The Praise of Hemp-seed". Both had died four years earlier.

In paper, many a poet now survives

Or else their lines had perish'd with their lives.

Old Chaucer, Gower, and Sir Thomas More,

Sir Philip Sidney, who the laurel wore,

Spenser, and Shakespeare did in art excell,

Sir Edward Dyer, Greene, Nash, Daniel.

Sylvester, Beaumont, Sir John Harrington,

Forgetfulness their works would over run

But that in paper they immortally

Do live in spite of death, and cannot die.

He was a prolific, if rough - hewn (wit rather than poet), writer with over one hundred and fifty publications in his lifetime. Many were gathered into the compilation All the Workes of John Taylor the Water Poet (London, 1630); and The Spencer Society brought out their Works of John Taylor ... not included in the Folio edition of 1630 (5 volumes, 1870 – 78). Although his work was not sophisticated, he was a keen observer of people and styles in the seventeenth century, and as such his work is often studied by social historians. One example is his 1621 work Taylor's Motto, which included a list of then current card games and diversions.

He achieved notoriety by a series of eccentric journeys e.g. he travelled from London to Queenborough in a paper boat with two stockfish tied to canes for oars, described in "The Praise of Hemp - Seed", which was re-enacted in 2006.

Taylor is one of the few early authors of a palindrome that can be credited as such: in 1614, he wrote "Lewd did I live, & evil I did dwel." He also wrote a poem about Thomas Parr, a man who supposedly lived to the age of 152. He was also the author of a constructed language called Barmoodan.

Many of Taylor's works were published by subscription; i.e., he would propose a book, ask for contributors, and write it when he had enough subscribers to undertake the printing costs. He had more than sixteen hundred subscribers to The Pennylesse Pilgrimage; or, the Moneylesse Perambulation of John Taylor, alias the Kings Magesties Water - Poet; How He TRAVAILED on Foot from London to Edenborough in Scotland, Not Carrying any Money To or Fro, Neither Begging, Borrowing, or Asking Meate, Drinke, or Lodging., published in 1618. Those who defaulted on the subscription were chided the following year in a scathing brochure entitled A Kicksey Winsey, or, A Lerry Come - Twang, which he issued in the following year.

By wondrous accident perchance one may

Grope out a needle in a load of hay;

And though a white crow be exceedingly rare,

A blind man may, by fortune, catch a hare.

- A Kicksey Winsey (pt. VII)