Background: The purpose of this study was to compare the accuracy of three different intraoral scanners (IOSs) and to evaluate the patients’ experience. Methods: Thirty subjects were scanned with three different IOSs (TRIOS Color®, iTero Element 5D®, and iTero Lumina®): a sample of 90 maxillary casts was collected. The inclusion criteria were permanent dentition, absence of defects during the dental impression, and complete record of the palatal vault. After the scanning procedure, patients were asked to answer a questionnaire (10 answers, scale from 1 to 10) to compare their experiences with iTero Element and iTero Lumina in the scanning procedure. Results: Differences were recorded in the upper central incisor region (f-ratio of 4.186 for Mesiodistal 1.1 and f-ratio of 4.222 for Mesiodistal 2.1, p < 0.05), while intercanine width Upper 13–23 showed the smallest f-ratio (0.226) when compared to the other results, followed by Mesiodistal 1.4 (0.433). Patients reported more comfort, less pain, decreased duration, and a better technology visualization of the impression with iTero Lumina. No significant differences concerning dryness of the mouth and gag reflex were found. Conclusions: The examined IOSs offer comparable accuracy in capturing dental arch dimensions. The interviewed patients expressed an overall preference for digital impressions performed with iTero Lumina, linked to increased comfort, painless practice, and a better technology visualization of the impression.