This paper presents the results of an exploratory study performed to evaluate the level of e-business disposition of Taiwanese tourism agents. The document relies on the experience of a similar previous exploratory study, web-design, e-business, tourism and information systems literature to demonstrate that a framework for the evaluation of the sophistication of websites in the industry sector can be drawn from an interpretative evaluation process. In this study, an analysis was carried out to compare the online tourism websites in terms of their level of sophistication. The exploratory study was conducted by evaluating 12 websites by a researcher and 5 experts. This also involved reviewing mayor websites (award winning) in the industry in order to use them as a standard of optimal desirability on a tourism website. The system chosen to carry out this evaluation was “benchmarking”. Four top internationally awarded websites in the category of tourism were evaluated by the experts. These experts evaluated all the websites according to a list of criteria suggested on a similar study and then compared the results of Taiwanese and benchmark websites. The results of this study are presented and analyzed to unveil relevant truths about the sophistication of tourism websites in Taiwan.