Anachronisms: The film takes place in the 1590s; yet, there are several references to a character's "tobacco plantations in America". There were neither tobacco plantations nor English colonies in America in the 1590s. The Roanoke colony failed in 1587, and tobacco monoculture did not begin in Virginia until the 1610s.
Continuity: Juliet's "blood" on the tomb moves around from shot to shot.
Revealing mistakes: When Will and Viola are in bed together the morning after their first tryst, the bed sheets are pulled to provide concealment in such a way that only someone not in the bed (and off camera) could physically do.
Revealing mistakes: When Will and Viola are in bed together the morning after their first tryst, just as Will falls off the bed you can see that he is wearing a pair of black shorts.
Factual errors: There are many discrepancies between the facts as portrayed in the movie and the known "facts" of Shakespeare's life and work, including the order in which he wrote his plays.
Continuity: Just after Lady Viola tears off her wig, accidentally revealing herself to be a woman, Sam (the actor playing Juliet) is shown standing next to her, his dress hanging down normally. However, in the next shot of Sam, his skirt is up around his shoulders, back where the Master of the Revels had raised it a few minutes earlier, erroneously believing Sam to be the woman in disguise.
Audio/visual unsynchronized: The sound of the tambourine, played by Shakespeare with the musicians at the dance where he meets Viola, continues after he has stopped playing.
Audio/visual unsynchronized: The audio for the choirboys at the church service is a line ahead of the visual.
Anachronisms: When Shakespeare and a musician are at a dancing event, the musician is holding a lute with fret markers on the fingerboard, but these were not used on instruments until the 1890s.
Continuity: When Romeo drinks the poison, he first opens the bottle, says what he has to say and in the next shot he opens the bottle again before he drinks the stuff.
Anachronisms: At the marriage of Viola and Wessex, the church bells are being change-rung. Change-ringing was invented by a Cambridge printer, Fabian Stedman, at the end of the 17th century, after the Restoration of the monarchy.
Continuity: When Viola, disguised as "Thomas Kent", departs from the boat after being pursued by Shakespeare, she takes off her hat to reveal a man's wig. Yet she has no such wig yet and asks her nurse to buy her one in a later scene. In addition, once she enters a corridor, she takes off the same hat she had previously removed to reveal her own hair.
Plot holes: How did the Queen know that Viola was "Master Kent" when she was a last-second replacement for Sam?
Plot holes: How did Viola learn of the audition when she wasn't at the bar, and the audition was scheduled for a half-hour after it was announced?
Plot holes: Lord Wessex, as a member of nobility, would not have risked the perilous journey to The New World to oversee his holdings, much less, move there. He would have sent a surrogate.
Factual errors: The real Philip Henslowe was a successful businessman who was never in debt to a loan shark. In fact, one of Henslowe's occupations was money lending.
Factual errors: According to Philip Henslowe's business ledger, kept from 1592-1603, he did not buy a play from Shakespeare for his theater, The Rose, during those years. Henslowe built The Rose primarily for his company, The Admiral's Men, the chief rival of Shakespeare's company, The Chamberlain's Men. Thus, Henslowe was not Shakespeare's patron, as he states in the movie, in 1593. However, it is believed that "Henry VI, Part One" was first staged at The Rose between 1589 and 1590, and that Shakespeare had performed at The Rose in 1592 or 1593 as part of Lord Strange's Men.
Factual errors: Shakespeare was still an actor and a relative unknown in 1593, although it is believed that the "Henry VI" plays, "Richard III", and "Comedy of Errors" were first staged by 1593.
Anachronisms: Shakespeare references his "Two Gentlemen of Verona" as he and Henslowe talk about the money Henslowe owes him. The film takes place in 1593; it is believed that "Verona" was first staged between 1594 and 1595.
Anachronisms: John Webster tells Shakespeare that his head was cut off in "Titus Andronicus". The film takes place in 1593; it is believed that "Titus" was first staged in 1594.
Plot holes: The film takes place in 1593; it is believed that "Romeo and Juliet" was first staged between 1594 and 1595.
Errors made by characters (possibly deliberate errors by the filmmakers): Shakespeare as Romeo tends to Mercutio by kneeling to Mercutio's right, and, in doing so, violates the first "rule" of stage acting, which is to never hinder the audience's view of the stage or the actors.
Continuity: In the first scene Mr. Fennyman says the play will take two weeks. Later Viola says her parents are gone to the country for three weeks' time. Yet when her wedding is announced, which is long before the play is performed, the parents are already back.