This work aims to produce poly(lactic acid) (PLA)/poly(alkylene furanoate)s (PAF)s fiber blends for textile applications and evaluates their microstructural, chemical, thermal, and mechanical properties. The work focuses on two PAFs with very different alkyl chain lengths, i.e., poly(ethylene 2,5−furandicarboxylate) (PEF) and poly(dodecamethylene 2,5−furandicarboxylate) (PDoF), which were blended in solution at various concentrations (in the range 2.5–10 wt %) with PLA, wet spun, and subsequently drawn. Light optical micrographs highlight that PLA/PEF blends present large and concentrate PEF domains, whereas PLA/PDoF blends show small and homogeneously distributed PDoF domains. The blends appear to be immiscible, which is confirmed also by scanning electron microscopy (SEM), Fourier−Transform Infrared (FT−IR) spectroscopy, and differential scanning calorimetry (DSC). Thermogravimetric analysis (TGA) highlights that the addition of the PAFs improves the thermal stability of the fibers. The drawing process, which was carried out at 80 °C with a heat setting step at 95 °C and at three draw ratios, improves the mechanical properties of the fibers upon the addition of the PAFs. The results obtained in this study are promising and may serve as a basis for future investigations on these novel bio−based fiber blends, which can contribute to increase the environmental sustainability of industrial textiles.