In brief comments outside a seaside Havana hotel on Friday, Jackson told reporters he intended to meet with local clergy about their concerns for the needs of the poor, and to discuss relations between Cuba, the United States and the rest of the Caribbean.
Asked whether he would meet with Gross, Jackson said: "I would like to."
Gross was arrested in December 2009 after authorities caught him importing restricted communications equipment into the country.
The case threw already cool US-Cuba relations into a deep freeze, although there have been signs of some thawing this year.
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Jackson has travelled to Yugoslavia, Syria and Iraq in the past to help gain freedom for US citizens jailed there.
In March 2011, shortly before Gross' trial, he appealed to Cuba to release the man on humanitarian grounds and offered to help mediate.
Former President Jimmy Carter came to Havana later that month, but left without Gross.
But the trip abruptly fell apart amid mutual recriminations as Richardson wasn't even allowed to see Gross, and referred to him in public comments as a "hostage."
Jackson has visited Cuba on several occasions and met with both former President Fidel Castro and current President Raul Castro. In 1984, he helped negotiate the release of 26 Cuban prisoners. Most of them went into exile.
On Friday, Jackson said he hopes to help continue healing the wounds of a five-decade divide between islanders and exiles.
"We hope for the day we will have the walls down, the bridges built," he said.