(1) Background: Water drinking is essential to reduce obesity in children, but effective means for implementation remain controversial. Our study assesses students’ and teachers’ use of and attitudes towards drinking fountains in two urban secondary schools. (2) Methods: In a cross-sectional study, answers from students and teachers to a 28- and 19-item questionnaire, respectively, containing closed- and open-ended questions and short interviews with the schools’ two principals were described and analysed using the question-specific number of responses as the denominator. (3) Results: Questionnaires of one hundred sixty-two students and ten teachers were analysed; 36.1% of students responded. Students viewed the schools’ two fountains as a good idea (73.3%,n= 118), recommended them to other schools (73.1%,n= 117), and felt able to distinguish healthy from unhealthy drinks (70.5%,n= 110). In contrast, 55.7% (n= 88) reported using the fountains regularly; over a week, 39.8% (n= 47) used them less than once; 26.3% (n= 31) used them one to two times. Only about a third (26.5%,n= 43) reported consuming more water since the fountains’ installation. Teachers’ responses were similar to students’; principals stressed planning and costs. (4) Conclusions: A discrepancy between a good attitude towards and actual use of drinking fountains may exist; school communities may need to look for measures to overcome it.