Great Diamond Island was a highly favored retreat for picnic parties, and Diamond Cove was easily accessible by sailboat from Portland or rowboat from nearby Peaks Island.

By the end of the century, steam ferries facilitated swift excursions for Maine's increasing number of tourists to the south end of Great Diamond Island. The Diamond Island Transportation Company, in particular, provided multiple daily trips on the steamer Isis, attracting sightseers with scenic cruise opportunities around the island. However, steamers couldn't reach Diamond Cove on the northeast end, limiting access to rowboats, sailboats, or on foot.