On the evening of May 12, 1862, the captain and officers of the Planter left the ship to spend the night on the shore. Robert and the rest of the slave crew had to stay on board under captain's orders. Later that night, Robert and the remaining crew stole out of Charleston Harbor. On the way out they picked up family members that hid in waiting. One of the biggest problems during the group's escape to freedom was to pass Fort Sumter without causing suspicion. He did this by putting on the captain's uniform and imitating him as they sailed past the guards. Before the escape, Robert had practiced the way the captain walked and appeared on deck. He successfully fooled the guards and the group of slaves steamed north. When they arrived in Union territory they surrendered the ship and gained their freedom.
Over 100,000 freed slaves became soldiers for the Union Army during the Civil War. With his experience sailing the Planter, Robert Smalls was allowed to return to piloting the ship under Union command. Only then could he be recognized officially as the pilot, a title not granted to slaves in the south. Eventually his contribution as a pilot for the Union war effort earned him the rank of Captain. During the 1870s, Robert Smalls served as a US congressman for South Carolina. He was buried in his hometown of Beaufort, S.C.