Trends in the relative energies and strain energies of the small double helicenes are identified.

Dispersion-corrected DFT is necessary to obtain proper geometries of the double helicenes.

The strain is largely localized to the shared naphthyl moiety.

NICS(0) values indicate a significant loss of aromaticity in the shared naphthyl moiety.

¹H and ¹³C NMR chemical shifts are computed as aids in identifying these molecules.