Destination image is among the most studied constructs in tourism research. Many researchers are still convinced that the rating scale method is the most accurate for assessing destination image. This study presents alternative methods of data collection, namely, free-sorting and reduced paired comparisons, and investigates their applicability in a Web-based environment. The study then subjects these data collection methods to empirical analysis and compares the judgment task’s effects on perceived difficulty, fatigue, and boredom, on data quality, and on perceptual maps derived with MDS. The findings demonstrate that these methods are more accurate whenever a large number of objects have to be judged, which is particularly the case for positioning and competitiveness studies.