The propagation of optical vortices nested in broadband femtosecond laser beams was studied both numerically and experimentally. Based on the nonlinear Schrödinger equation, the dynamics of different multiple-vortex configurations with varying topological charge were modelled in self-focussing and self-defocussing Kerr media. We find a similar behavior in both cases regarding the vortex–vortex interaction. However, the collapsing background beam alters the propagation for a positive nonlinearity. Regimes of regular and possibly stable multiple filamentation were identified this way. Experiments include measurements on pairs of filaments generated in a vortex beam on an astigmatic Gaussian background with argon gas as the nonlinear medium. Spectral broadening of these filaments leads to a supercontinuum which spans from the visible range into the infrared. Recompression yields <19 fs pulses. Further optimization may lead to much better recompression.