TheCommonwealth Ministerial Action Group (CMAG) will beled by its Vice-Chair, Guyana's Vice-President and Minister of Foreign Affairs Carl Greenidge.
British Prime Minister David Cameron last month had asked the Maldives to open up its politics and release all remaining political prisoners after his meeting former jailed president Mohamed Nasheed, who was granted special leave for urgent spinal cord surgery in the UK.
Besides Jaishankar, the Commonwealth delegation includes Kenya's Cabinet Secretary for Foreign Affairs and International Trade Amina Mohamed.
CMAG is a political body comprising nine foreign ministers.
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It acts on behalf of Commonwealth Heads of Government as the custodian of the Commonwealth's fundamental political values including democracy, the rule of law and human rights.
"The mission is aiming to develop a first-hand understanding of the situation on the ground and to consider how the Commonwealth can continue to assist in advancing Commonwealth values and principles, and to support Maldives in building stronger democratic institutions and culture," Henley said.
Nasheed, 48, became the first democratically-elected president of the Maldives in 2008 and served for four years before he was toppled in what he called a coup backed by the military and police. He was sentenced to 13 years in jail on terrorism charges relating to the arrest of an alleged corrupt judge in 2012, when he was still in power.