Interesting question, and I don't have a ready answer.
There was almost no blockade running in or out of Texas going on at the end of 1863 using steam runners, although there was a continual stream of small sailing craft that could carry anything up to a few dozen bales. Seems kind of unlikely that Gentry would have divided up his shipment in that way, on multiple vessels going to multiple ports, on whatever schedule.
This shipment may have ended up on one of the next three steam runners that left Galveston after Gentry's inquiry, Isabel, Alice, and Lavinia (ex-Harriet Lane) ran out together on the evening of April 30, 1864, that I do discuss some in the book. That's not a very firm answer, but it seems a possibility to me.