Islander was modelled on Sea Bird, a 25-foot V-bottom boat that was designed by Charles D. Mower with input from Captain Thomas Fleming Day. Pidgeon built Islander from 1917 to 1918 using only $1,000 of materials. Islander was built mostly from oak, Douglas fir, and Oregon pine. Writing about his voyage later, Pidgeon commented that Islander "proved to sail well, and all remarked on the ease with which she handled."