Around the time it peaked in intensity, Lenny's forward speed decreased in response to light steering currents between two ridges. Despite favorable conditions for strengthening, the hurricane weakened as it turned to an eastward drift, possibly due to the upwelling of cooler waters. Late on November 18, Lenny's eye moved over Saint Martin with winds of . After continued weakening, the hurricane struck Anguilla and Saint Barthélemy the next day. It turned southeastward while still drifting, bringing heavy rainfall and strong winds to the islands across the northeastern Caribbean. Late on November 19, Lenny weakened to tropical storm intensity after increased wind shear exposed the cyclone's center from the deepest convection. Early on November 20, the storm made landfall on Anguilla, although by then the center had become difficult to locate. Later that day, the cyclone exited the Caribbean, continuing its southeast track. On November 21, Lenny turned to the northeast and weakened to a tropical depression. The deep convection was located at least east of the increasingly elongated center. Lenny turned to the east for the final time early on November 22, dissipating on the next day about east of the Lesser Antilles.