Understanding hand–paddle interaction is essential for optimizing performance and preventing injury in kayaking, yet coaches still lack objective, practical tools. We present a soft, instrumented glove that measures and dynamically maps palmar pressure throughout the stroke cycle. A matrix of piezoresistive sensors is integrated into the glove and connected to dedicated electronics housed in a waterproof enclosure. A viscoelastic model converts sensor resistance into forces, enabling time-resolved 3D mapping of contact mechanics. Data are transmitted via Bluetooth Low Energy (BLE). Experimental validation on a kayak ergometer across multiple cadences demonstrated accurate measurements (per-sensor root mean square error (RMSE) of ±2 N), clear delineation of pull and push phases, evolving pressure distribution over the motion, and a peak total right-hand force of 186 N at high cadence. Beyond feasibility, these results position the glove as a practical training aid: it supports athlete-specific load monitoring and the early detection of potentially problematic movement patterns.