At 19 years of age, Charles Stephen Kolodgy set sail on his first recorded voyage aboard the the SS Bethore (a steamship consigned to the Ore Steamship Corp), which left port in New York on 18 January 1924 and sailed to Cruz Grande, Chile. According to ship logs, the crew started with 48 persons, but three deserted in Balboa on 27 January 1924. On 7 February, he left port and enroute to the US with the crew of 45 on 29 February 1924. On the voyage he served as a 'messman' in the galley, a station typical of new sailors cutting their teeth in sailing.
A few months later, on 5 May 1924, Charles once again set sail, leaving Maryland aboard the S.V. Harkness (a Standard Oil ship) from Baltimore, MD to Tampico, Mexico. Again, he was a messman for the voyage. The ship arrived at New Orleans on 18 May after 4 days at sea. According to the ship's log, he was 5'8" tall and weighed 155 lbs and was described as "Hebrew".
On 12 September 1924, Charles signed on for a third voyage. This time, it was the SS Santa Veronica (consigned to the American and Cuban Line) which set sail on 29 November for Havana. Of a total crew of 31 men, Charles was one of only seven Americans which included the Captain. Charles was no longer a 'messman', he was now an 'Ordinary Seaman' as recorded with an 'o.s.' for his position on the ship's log. The ordinary seaman is a position on deck that serves as an apprenticeship for becoming an 'able seaman'.
On 31 October 1927, Charles filled out an application for another voyage.