Myosin Va is a processive, actin-based molecular motor that is critical for organelle transport. While transporting intracellular cargo, myosin Va faces significant physical barriers and directional challenges created by the complex actin cytoskeleton, a network of intersecting actin filaments and actin bundles. We have created an in vitro model system of fascin cross-linked unipolar actin bundles. While walking on an actin bundle, a single myosin Va motor switches filaments within the bundle with a high probability (24%). Although a single myosin Va is sufficient to transport cargo in vitro, intracellular cargo transport is driven by multiple motors. To understand the collective behavior of multiple motors, we have linked two myosin Va motors, with only one head of each motor labeled with either a red or green Qdot, via a third Qdot which acted as a cargo. If each motor walks on a different actin filament within the bundle, then the two motors may experience an off-axis load. The velocity and the run length of the 2-motor complex was reduced significantly from that of a single motor, suggesting that the motors interfere with each other's motion. Interestingly, the leading motor takes ∼10% back steps, indicating that it experiences a resistive load from its partner. Both the run length of the complex and the step lifetimes of the motors were correlated to the inter-motor distance, with the run length decreasing and the step lifetimes increasing with greater motor separation. Our data suggest that the two motors step independently when close together. However, when far apart, tension increases in their cargo-linkage, which results in inter-motor mechanical coupling. This study will provide insight into the mechanism of how multiple motors mechanically interact to transport cargo in vivo.