Based on four years of butterfly monitoring in four contrasting natural habitats on St. Eustatius, we document large and consistent differences in the butterfly species assemblages in the different habitats and compare the butterfly assemblages of the three windward Dutch islands to those of other islands of the Lesser Antilles. Seven new species records were established for St. Eustatius, thereby updating the butterfly list to a total of 32 species. Pieridae were the most numerically abundant group of butterflies (48%), followed by Lycaenidae (26%), Hesperiidae (12%), and smaller numbers of both Heliconiinae (6%) and Charaxinae (5%). Heliconiinae and Charaxinae both showed a significant dependence on the moister, wind-sheltered habitats of the volcanic slopes and crater of the Quill, but this dependence was particularly strong for Heliconiinae. The butterfly faunas of the windward Dutch islands numbered a total of 44 species. The presence of larval host plants needed for local reproduction was confirmed for all but two species. Cluster analysis separated the butterfly faunas of these and the surrounding islands into two groups. The more speciose butterfly assemblages of Saba, St. Eustatius, and St. Martin clustered together with the those of the surrounding higher islands of Antigua, Montserrat, Nevis, and St. Kitts, while the poorer faunas of the low-lying islands of Anguilla, St. Bartholomew, and Barbuda formed a separate cluster and had a lower species richness particularly in the Heliconiinae and Charaxinae. Based on consistent effects of elevation on butterfly faunas, at both geographic scales (between areas on St. Eustatius and between islands), our results suggest that island maximum elevation is the overriding factor explaining the distribution of butterfly faunal richness in the northern Lesser Antillean islands studied.