The present study investigates, in the laboratory, the behavior of a self-propagating barotropic cyclonic vortex colliding perpendicularly with aligned circular cylinders representing an island chain. During the experiments, four parameters were varied: G, the gap width between the cylinders; d, the diameter of the incident vortex; Y_dis, a parameter expressing the initial vortex positions; and D_isl, the total length of the ‘middle’ island. It has been observed that, as long as 0.07 ≤ G/d ≤ 0.4, the flow within the vortex was funneled between two cylinders at one of the gaps and a dipole generally formed for all the configurations of the cylinders and Y_dis, much like water ejected from a circular nozzle generates a dipole ring. After the dipole formed, the cyclonic part of the dipole became dominant. Depending on the value of D_isl, a relatively large offspring (i.e. a cyclonic vortex) was produced either directly from the cyclonic part of the dipole, or from the remnant of the original vortex at the gap positioned just South of the gap where the dipole formed. The vortex centre position, radius and circulation, before and after the interaction, were computed from its velocity field. It was found that, for 0.16 ≤ G/d ≤ 0.4, intense vortices (i.e. with large circulation) experienced greater amplitude loss than weak vortices, and in general, the number of offspring was one, independently of the configurations and Y_dis. The formation of both a dominant cyclone and an anticyclone (i.e. a dipole) downstream of the island chain is in agreement with recent oceanic observations of North Brazil Current (NBC) rings interacting with the Lesser Antilles in the Eastern Caribbean Sea. Since the passages of the Lesser Antilles have values of 0.07 ≤ G/d ≤ 0.3, the oceanic observations might be explained by the experimental results reported in this paper.