Due to the increasing consciousness of a healthy diet and pursuit of convenience among consumers, the market for fresh fruit is on the rise, and the melon is among the most welcome of fruits for its sensory attributes and nutritional properties. Consumption safety of cut fruit remains an issue of concern that may affect public health. This study aimed to perform the microbiological characterisation of a melon, Cucumis melo L. var. “Piel de Sapo”, cut by retailers, wrapped in plastic cling film and kept at room temperature in local fruit shops. In addition, the possible transfer of relevant foodborne pathogens, during slicing, from the peel to the interior of the melon, and bacterial growth, were also evaluated when the melon slices were stored at abusive temperatures for 2 days. In this pilot study, a low number of samples were characterised microbiologically (26 cut melons), and some isolates were identified by 16S rRNA sequencing. No Listeria spp. or Salmonella spp. were detected in any of the samples, while Escherichia coli and Staphylococcus aureus were present in four and six out of twenty-six samples, respectively. Following artificial contamination of melons with cocktails of Salmonella spp., E. coli and Listeria monocytogenes, it was observed that, despite the smaller number of L. monocytogenes recovered, all the pathogens were transferred from the contaminated peels to the interior of the melons. Furthermore, over storage time, significant differences were observed (p < 0.05) between the counts obtained from melon slices immediately after cutting (0 h), and after 24 and 48 h at 20 °C, with an increase of about 4 log CFU/g in all the pathogens. In conclusion, some cut melons classified as microbiologically unacceptable or unsatisfactory are being sold in local fruit shops in the Porto Metropolitan Area, Portugal. Although absent in the samples analysed, Salmonella spp. and L. monocytogenes, if present, can be transferred from the outside to the inside of the fruit by the cutting blade and, if not consumed immediately and stored at abusive temperatures, this ready-to-eat product poses a risk of infection. This pilot study, performed for the first time in Portugal under these conditions, clearly demonstrates the need for education campaigns to alert local sellers and consumers of the risk posed by cut melons.