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Chocolate is a food product that is loved by many because of its desirable qualities. These qualities include a shiny gloss on the surface, snap when the chocolate is broken, and a smooth texture that becomes apparent only when the chocolate melts in the mouth. Aim of this paper is the application of a 2-step quality assessment to fine chocolate products, e.g. the well-known Italian “Cremino”, distributed worldwide. The first step consists in monitoring the temperature fluctuation during the distribution from the production plant to the point of demand, usually a candy shop. The second step deals with the simulation of the monitored shipment in a temperature and humidity controlled system. The simulation of the physical and environmental conditions generated during the real shipment is followed by chemical analysis and sensitive analysis conducted separately on non-stressed products (the so-called “time zero products”) and stressed products. The effects of temperature are evaluated by comparing stressed and time zero products belonging to the same production batch. The analyses are repeated after 6 months in order to evaluate the effects due to time and shelf-life erosion. The obtained results demonstrate the importance and criticality of packaging and containment solutions to face unexpected temperature variations during the logistic journey to the final consumer.