Sailors' Valentines originated during the whaling era (mid 1800s) and were reportedly made by sailors aboard ships for their loved ones back home. More likely, however, the Valentines were made by people on the island of Barbados and sold to the sailors. Barbados was a port of call for both American and English ships. The intricate work could hardly have been accomplished on boats rolling at sea.

These octagonal wooden boxes were usually created from Spanish cedar called cedrella. Others were crafted using fine mahogany. The antique boxes were sometimes locked with a key and ranged in size from eight to fifteen inches. Craftspeople began creating the Valentine by lining the inside of the box with colored paper or sometimes using newspaper. Hide glue was used to fasten the shell work. The final step included inserting glass over the top for protection. Sailor's Valentines were given as gifts of love from sailors to wives, mothers, and sisters upon their return home from a voyage at sea.

Today, Sailors' Valentines are sought-after collectibles, both antique and new.