Skiff and Skiff Sr.’s fishing boat, the Mary Rose, is named after Skiff’s deceased mother. At the beginning of The Young Man and the Sea, the Mary Rose sinks, and sports a broken engine and rotten planks. While repair is possible, it would be costly—so Skiff Sr. doesn’t think it’s worth pursuing. The Mary Rose symbolizes Skiff’s mother, its sinking and disrepair mirroring Skiff Sr.’s depression in particular. Without her physical presence, the family is left grieving. However, Skiff believes anything broken can be fixed, that his father can heal from their shared loss. He works hard to raise the money needed to fix the Mary Rose, setting lobster traps and later harpooning a giant bluefin tuna. He also inspires his father to leave the house and pursue sobriety. After selling his tuna, Skiff repairs the Mary Rose, symbolizing his and his father’s healing process: This doesn’t mean they no longer miss Mary Rose, but they’ve managed to move on while honoring her memory.

Skiff’s skiff is a small wooden boat built by his father; it’s not a proper fishing boat, but sports a motor. Both Skiff and Skiff Sr. are named Samuel but use the nickname “Skiff” to mirror the hardy nature of these small boats.