We study the evolution of the decaying active region NOAA 12708, from the photosphere up to the corona using high resolution, multi-wavelength GREGOR observations taken on May 9, 2018. We utilize spectropolarimetric scans of the 10830 Å spectral range by the GREGOR Infrared Spectrograph (GRIS), spectral imaging time-series in the Na ID2 spectral line by the GREGOR Fabry-Pérot Interferometer (GFPI) and context imaging in the Ca IIH and blue continuum by the High-resolution Fast Imager (HiFI). Context imaging in the UV/EUV from the Atmospheric Imaging Assembly (AIA) onboard the Solar Dynamics Observatory (SDO) complements our dataset. The region under study contains one pore with a light-bridge, a few micro-pores and extended clusters of magnetic bright points. We study the magnetic structure from the photosphere up to the upper chromosphere through the spectropolarimetric observations in He II and Si I and through the magnetograms provided by the Helioseismic and Magnetic Imager (HMI). The high-resolution photospheric images reveal the complex interaction between granular-scale convective motions and a range of scales of magnetic field concentrations in unprecedented detail. The pore itself shows a strong interaction with the convective motions, which eventually leads to its decay, while, under the influence of the photospheric flow field, micro-pores appear and disappear. Compressible waves are generated, which are guided towards the upper atmosphere along the magnetic field lines of the various magnetic structures within the field-of-view. Modelling of the He i absorption profiles reveals high velocity components, mostly associated with magnetic bright points at the periphery of the active region, many of which correspond to asymmetric Si I Stokes-V profiles revealing a coupling between upper photospheric and upper chromospheric dynamics. Time-series of Na ID2 spectral images reveal episodic high velocity components at the same locations. State-of-the-art multi-wavelength GREGOR observations allow us to track and understand the mechanisms at work during the decay phase of the active region.