The authors examine the relationship between positive online reviews, using their lower and upper limits, and the evaluation perceptions of hotel managers. This study uses a qualitative and quantitative analysis, based on 34 hotels in the Douro Valley, in the northern region of Portugal, and a sample of 2222 positive online reviews with a lower limit (17.19%) and 10,707 positive reviews with a higher limit (82.81%), out of a total of 12,929 online reviews on Booking.com . This article explores the ways in which sustainable practices and the overall guest experience impact the financial performance and satisfaction, managers’ professional contentment, service quality index, active professional participation, and competitive focus and communication management. The findings demonstrate that several of the characteristics indicated in the managers’ assessment have a substantial impact on how valuable customer online reviews are. The purpose of this research is to close a theoretical gap about the relationship between the managers’ assessments of each hotel in the Douro Valley and the quality perceptions of the customers as established by their interactions with the establishments. Our sample comprises all hotels in the Douro Valley with ratings ranging from 1 to 5. Policymakers can utilize the suggested strategy to promote territorial development in the wine area, and professionals can use it to enhance the quality of their services and the strategies for success that will be produced.