The painting has Jessie Logan racing in Tasman Bay adjacent to the Boulder Bank, Nelson. She has a moderate sea breeze heading up to the top mark where she is just bearing away with Oyster in pursuit. The Nelson Lighthouse and light-keepers buildings can be seen on the left. She is seen here in 1902 before the The Cut was opened in 1906 to allow shipping to enter Port Nelson through the Boulder Bank without going around Haulashore Island. Jessie Logan is the oldest ‘purpose built gaff rig racing yacht’ in the world and is still racing to this day. She was built in his Devonport waterfront yard by Robert Logan Senior in December 1879 - January 1880 to compete in the Auckland Anniversary Regatta that year.
Jessie Logan was again successful in Wellington despite her real unsuitability for Wellington Harbour with her low freeboard, lightweight and extreme rig. In January 1892 she was sold to Nelson where she was raced for another thirteen years under progressively reduced rigs. By 1905 she had become outclassed and was converted to a launch.
She then spent the next 75 years in all sorts of menial tasks as an oil launch. After 1918 she was servicing soldier settlements and taking children to school in Pelorus Sound, for example. Adrian Hayter, the famous yachtsman and circumnavigator used her for fishing out of Nelson for some years. In the 1980s she came ashore in a storm at Nelson and became badly damaged.