This study investigates the impact of combined texturing by micromachining and chemical functionalization on the wetting behavior and water condensation on stainless steel 304. The transition from Wenzel to Cassie-Baxter or impregnated Cassie-Baxter regimes is investigated. Understanding this transition is critical for advancing surface engineering, as it enables precise control over wetting behavior for various applications. Herein, we report on the wire EDM (wEDM) machining on stainless steel 304 to produce two distinct microstructure patterns with directional canals or pyramidal structure, and their performance in water condensation. These patterns significantly impact water condensation performance. wEDM is employed to create surface roughness, followed by phosphoric acid treatment and chemical functionalization with trichloro-1H,1H,2H,2H-perfluorooctyl silane. Contact angle measurements reveal a synergistic effect between groove direction and silane coating, leading to hydrophobic surfaces and dropwise water condensation. Specimens with directional canals exhibit a contact angle of 150°, while specimens with pyramidal structures exhibit 151o. Roll-off angle experiments showcased distinct behavior among specimens featuring canals or pyramidal structures. Specimens with canals exhibit notably lower roll-off angles compared to both flat surfaces and those with pyramidal patterns, leading to a dependence of roll-off angles on the orientation of canals. In humid environments, micromachined specimens exhibit superior water condensation capability compared to untreated SS304 surfaces. Chemically functionalized grooved specimens present larger condensate droplet diameters than flat surfaces. An enhancement in water condensation and a sevenfold higher latent heat transfer coefficient is reported. Specimens with chemical functionalization achieve corrosion protection with an efficiency reaching 82.9%.