Photoacoustic imaging (PAI) combines optical contrast with ultrasound spatial resolution and can be obtained up to a depth of a few centimeters. Hand-held PAI systems using linear array usually operate in reflection mode using a dark-field illumination scheme, where the optical fiber output is attached to both sides of the elevation plane (short-axis) of the transducer. More recently, bright-field strategies where the optical illumination is coaxial with acoustic detection have been proposed to overcome some limitations of the standard dark-field approach. In this paper, a novel multiangle long-axis lateral illumination is proposed. Monte Carlo simulations were conducted to evaluate light delivery for three different illumination schemes: bright-field, standard dark-field, and long-axis lateral illumination. Long-axis lateral illumination showed remarkable improvement in light delivery for targets with a width smaller than the transducer lateral dimension. A prototype was developed to experimentally demonstrate the feasibility of the proposed approach. In this device, the fiber bundle terminal ends are attached to both sides of the transducer’s long-axis and the illumination angle of each fiber bundle can be independently controlled. The final PA image is obtained by the coherent sum of subframes acquired using different angles. The prototype was experimentally evaluated by taking images from a phantom, a mouse abdomen, forearm, and index finger of a volunteer. The system provided light delivery enhancement taking advantage of the geometry of the target, achieving sufficient signal-to-noise ratio at clinically relevant depths.