We report a simple and effective approach to organic molecules exhibiting bright circularly polarized luminescence (CPL) by combining a chiral cyclic molecular scaffold and multiple excimer‐enabling moieties. An α‐cyclodextrin (CyD) scaffold was modified with six pyrenyl groups to obtain pyrene–cyclodextrins (PCDs) in a one‐step synthesis from commercially available compounds. The PCDs exhibited high molar extinction coefficients (ϵ≈105 M−1 cm−1), polarized emission with a good dissymmetry factor (|glum|≈10−2), and quantum yield (Φf≈0.5). Owing to the excellent photophysical properties of the PCDs, the circularly polarized luminescence brightness (BCPL) reached 340 M−1 cm−1. Photophysical and chiroptical studies of the PCDs with only five pyrene units and with linkers of various lengths connecting the CyD with the pyrene units revealed that the formation of a pyrene excimer in a spatially crowded environment is crucial for CPL anisotropy. This study paves the way for the development of bright CPL organic molecules.