High levels of ab initio (MP2, CASSCF, CASPT2N) and density functional (Becke3LYP) theory have been used to assess the homoaromatic character of some strained semibullvalenes. Based on geometric, energetic, and magnetic criteria (magnetic susceptibility exaltations and the nucleus independent chemical shifts, NICS), C-s semibullvalene itself is not aromatic, but the C-2 upsilon transition state for its Cope rearrangement is highly bishomoaromatic. Appropriate annelations destabilize the C-s geometries, and the bishomoaromatic structures are the only minima for several semibullvalenes : 1,5-methane; 2,8:4,6-bisethano and -bismethano; and 2,8-monoethano. In contrast, the 4,6-ethanosemibullvalene is predicted to be localized and not homoaromatic. Inclusion of dynamic electron correlation is very important for computing the geometries and relative energies of the delocalized structures. To aid experimental investigations, the UV and C-13 NMR spectra of some of the semibullvalenes have been predicted. Long-wavelength UV absorptions and down-field C-13 NMR chemical shifts for C-2,C-8,C-4,C-6 are characteristic.