We investigate the OH stretch vibrational frequency shifts of a prototype photoacid, 2-naphthol (2N), when dissolved in solvents of low polarity. We combine femtosecond mid-infrared spectroscopy and a theoretical model based on the Pullin-van der Zwan-Hynes perturbative approach to explore vibrational solvatochromic effects in the ground So and the first electronically excited (1)L(b) states. The model is parametrized using density functional theory (DFT), at the B3LYP/TZVP and TD-B3LYP/TZVP levels for the 2N chromophore in the S(0) and (1)L(b) states, respectively. From the agreement between experiment and theory we conclude that vibrational solvatochromic effects are dominated by the instantaneous dielectric response of the solvent, while time-dependent nuclear rearrangements are of secondary importance.