We present a molecular dynamics study into the thermotropic liquid crystalline phase behaviour of a coarse-grained model of a rigid bolaamphiphilic molecule. The model consists of 11 spherical beads held in a fixed linear arrangement, where the two opposing terminal beads are self-attracting, mimicking hydrophilic segments and the remaining internal beads, as well as cross-bead interactions, are softly repulsive, mimicking hydrophobic organic segments. The effect of the model’s end bead self-attraction strength on liquid crystalline phase behaviour is studied. Coexistence points between the smectic A, nematic and isotropic phases exhibited by the model are determined following a thermodynamic integration pathway, using equations of state constructed by multiple histogram reweighting of simulation data. Variants of Gibbs–Duhem integration are used to trace pressure–temperature coexistence curves. Under isobaric conditions, the effect of increasing the end-group self-attraction on the nematic–isotropic coexistence temperature is relatively small; however, the nematic phase stability is reduced at the expense of a significant increase in the smectic A–nematic coexistence temperature. Lower temperature simulations show the approximate smectic A–crystalline transition temperature to be only weakly dependent on the strength of the end-group self-attraction.