Nasheed was originally due to leave on Sunday in line with a deal brokered by diplomats from neighbouring India and Sri Lanka as well as former colonial power Britain.
But the former leader refused a government request to leave a relative behind to act as a guarantor liable to prosecution if he failed to return to serve the rest of his 13-year sentence, leading to a tense back and forth over conditions.
One of his international lawyers, Jared Genser, said Nasheed had spoken with the US Secretary of State by telephone at Male international airport shortly before he boarded a Sri Lankan airlines flight to Colombo before transiting to Britain.
"Nasheed on a call with US Secretary of State John Kerry," Genser said in a tweet containing a photo of Nasheed.
It was not clear what they discussed, but Kerry had previously criticised the administration of strongman President Abdulla Yameen during a visit to neighbouring Sri Lanka last year.
Kerry described democracy as "under threat in the Maldives" at the time, saying Nasheed was imprisoned without due process.
Nasheed was convicted on terrorism charges in 2015 relating to the arrest of an allegedly corrupt judge in 2012, when he was still in power.
Lawyers for Nasheed have hit out at the government for delaying treatment on his spinal cord, but his Maldivian Democratic Party (MDP) has agreed to an amended condition of providing a relative to communicate Nasheed's whereabouts while abroad.
"President Nasheed told members of his family that he wasn't prepared to put their freedom in jeopardy in order to secure his own," the MDP said in a statement.
The Maldivian government in a statement insisted that all legal formalities had been followed before Nasheed was allowed to leave.
"It is standard procedure for any prisoner who applies to travel abroad, for medical treatment, to sign a guarantee," Maldivian Foreign Minister Dunya Maumoon said in a statement. "I am glad all relevant legal documentation is completed.
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