When Charles fled Hampton Court, he went in the company of three other men; Sir John Berkeley, John Ashburnham, and William Legge. Arriving at Titchfield, Charles sent Ashburnham and Berkeley to meet the Governor of the Isle of Wight, Robert Hammond, and try and feel him out while Charles would wait at Titchfield. In other words, he sent the two messengers ahead to find out if Hammond was sympathetic towards the King. Pauline Gregg, in her biography of Charles, states that Ashburnham was in part to blame for the delay, as he may have convinced the King to go to the Isle of Wight instead of the continent. Bad weather delayed Ashburnham and Berkeley so that they were not able to meet Hammond until the evening of November 12. The King’s messengers seem to have bungled their meeting with Hammond, informing him of the King’s location and that he had escaped from Hampton Court for fear of being assassinated. Hammond did not quite know what to make of this, and the three returned to Charles to decide from there.

By the morning of November 13, Charles' escape was known at Westminster, and Parliamentary forces worked to close down the ports preventing his crossing to France. Specifically, Charles had expected a ship from Southampton in case he could not get an assurance from Hammond for his safety (and likely, safe passage). The ship never came. With no other option, and Hammond promising to keep the King safe from harm (but not guaranteeing freedom of movement) Charles went with his three attendants and Hammond to the island. Hammond wrote to the Earl of Manchester at 4 am on November 14 that the King was being held on the island, and asked for further instructions.

Part of the problem of knowing exactly what unfolded between the King leaving Hampton Court on November 11 and arriving at Wight on November 13 is that the sources themselves present different information. The main sources available are the letter of Charles on November 11 (mainly about keeping his belongings safe), the letter from Hammond on November 14 (both found in the Lord’s Journal Volume 9, pp. 520, 525), and then the memoirs of Berkeley and Ashburnham. Berkeley’s memoirs were written after the Restoration, and published in 1699; Ashburnham’s narrative of events was written sometime after the events of 1647, and were eventually published in 1830. Both Berkeley’s Memoirs and Ashburnham’s Narrative were written enough after the fact that the details fuzz, and both men were writing to clear themselves of culpability from the King’s capture. Between the multiple sources, it seems likely that Berkeley let slip that the King was near to Hammond before any assurances were given. Once the ship from Southampton failed to appear on the horizon, there was little for the King to do except agree to head to the castle at Wight. There were Royalists on the Isle of Wight, and Ashburnham suggested that the King reside with one Sir John Oglander while they find out the disposition of Hammond. After bungling the negotiations (which Ashburnham blames on Berkeley, and Berkeley claims he was following Charles’ instructions “word for word”, and that Ashburham had told him to speak first), Charles was really left without many options. The coast had been closed down, he was concerned about being taken by an increasingly radical army, and felt his best assurance for safety was with Hammond, even if that meant being imprisoned again.