Liam Goddard, 27, stole cash from safe boxes and the premises, alcohol and a tablet worth more than £400 during the crime spree, said Adam Walker, prosecuting.
On one night he broke into three premises in different parts of the city in five hours.
Arrested for the first two burglaries, he was abusive to a police officer and told her that someone could wait outside the police station and follow her home.
Through his barrister Anastasis Tasou, Goddard claimed the crime spree was due to taking crack cocaine after finding his parents dead from heroin overdoses.
The Recorder of York, Judge Sean Morris told him: “Everybody has tragedies in their lives though none as bad as yours, but that doesn’t give you the right to make other people’s lives a misery.”
Goddard, of no fixed address, was jailed for 27 months.
A map of most of Goddard’s crimes with the city centre shaded in orange
Mr Tasou said Goddard had never worked for a living.
Mr Walker said Goddard’s crimes started with attempted robbery in 2008 when he was still a juvenile and included a 30-month prison sentence in 2016 for conspiracy to supply Class A drugs.
In total he had 64 previous convictions including theft, criminal damage and threats to kill.
On September 14 this year, Goddard broke into Pepperoni Palace in Clifton Moor at 3am where he took cash, the tablet and alcohol worth together nearly £700 and Rose Café in Haxby Road, where he took cash and an iPhone.
Released while police investigated the crimes, he carried out more raids on October 7, said Mr Walker.
Goddard raided a guesthouse in north York, stealing more than £200 from its safe box, between midnight and 3am.
At 3.45am he was at Mrs Greedy’s Café in Burton Stone Lane where he stole cash and a bike.
At 4.45am he stole a separate bike from the city centre, which he used to get to Naz Spice in Heworth, which he raided at 5.10am.
He kicked in its door and stole various items. The takeaway lost several hours’ takings because it was closed awaiting scenes of crime officers.
Mr Tasou said Goddard had had mental health problems most of his life and had started smoking cannabis as a child. While in prison on remand, he had taken courses to better himself, including a qualification enabling him to work on building sites.
He had been offered a hostel place and could probably get a job. “Maybe this defendant could start leading a productive life,” said Mr Tasou.