As oil and gas exploration goes toward deeper fields in the Brazilian industry scenario, offloading operations emerge as the most viable option to drain production. However, these operations demand expensive resources, such as shuttle tankers and support boats; operational risks, which despite being managed, limited, and mitigated to be as low as reasonably possible, are still present in some stages (i.e., ship’s approximation to the oil rig, mooring, hose connection, and so forth); and environment limiting parameters (i.e., wave height, surface-current direction, wind speed and direction, and so forth). Therefore, in this paper, we propose using unmanned aerial vehicles (UAVs) in an autonomous mode to carry out the messenger line from the shuttle tanker to the floating, production, storage, and offloading (FPSO) unit or the floating storage and offloading unit (FSO) instead of line-handling (LH) boats (for conventional operations that use those resources) or the messenger-cable-launching guns (for dynamic positioning operations). This represents a viable alternative solution to reducing costs and risks in these tasks and a possibility to eliminate some meteorologic and oceanographic limiting conditions to operations, because the UAV will be susceptible only to wind conditions, and not to sea and visibility conditions, like LHs are. We present the simulated results of the proposed methodology using a robotic operating system (ROS) and the economic gain [derived from cash-flow-cost reducing of operations, payoff time of the investment, net present value (NPV), and internal rate of return] of applying this technology, evaluating its use in a realistic scenario based on a real deepwater oil field in Brazil. The developed controller behaves very well, and simulations showed robust results. In addition, the economic study presents the proposal’s attractiveness.