Prolonged durability in outdoor environment and ease of application are highly required features for self-healing coatings. To this end, a novel transparent and self-healing nanocomposite for optical applications, based on Diels-Alder (DA) chemistry is developed in this work. First, a novel, highly soluble, bismaleimide enabled a simple coating fabrication by coupling with furan-functionalized polyacrylates in industrially relevant solvents. The resulting crosslinked coatings exhibited high transparency and complete absence of color, as assessed by UV-vis spectroscopy. Their thermal behavior and the conditions required by the healing process were significantly affected by the degree of furan/maleimide functionality of the system. Secondly, the addition of a small amount of a commercial antioxidant stabilized the optical properties against photo-oxidative weathering, both on clear and titania-pigmented coatings, as determined by colorimetric analysis. Finally, dispersion of silica nanoparticles in the DA-based matrix allowed to enhance the surface hardness of the coatings, while retaining the self-healing ability.