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Like many young aristocrats in 18th century England, Calvert was sent on a Grand Tour of Italy, travelling there from 1724–5. During this time he studied Italian architecture and antiquities, collecting many items which were sent back to the family home at Woodcote Park in Surrey.

In 1727 the young Benedict Calvert was sent to Maryland by his older brother Lord Baltimore, with instructions to take over the governorship of the colony, replacing his cousin Captain Charles Calvert. The handover of power from cousin to cousin was not entirely smooth. Captain Calvert insisted on retaining fifty percent of the 3 pence tobacco duty which was his due under legislation passed in 1727. Benedict was not impressed, and his younger brother Cecilius wrote to him that family opinion in

Calvert had tuberculosis and died of consumption on board the family ship, The Charles on 1 June 1732, while returning to his home in England. He was buried at sea. He left an estate worth around ten thousand pounds sterling, a large sum at the time, to his younger brother Cecilius Calvert.

Calvert had no children of his own, but he was godfather to Elizabeth Calvert, daughter of his cousin Captain Charles Calvert. In his will, which he drew up before leaving Maryland, he left her a slave boy named Osmyn. The town of Leonardtown, Maryland is named in his honor.