In 1894, while he was living in Glendalough, he bought a Dublin Bay Water Wag, a 13-foot type of sailing boat usually sailed in Dún Laoghaire, pear-shaped with a single gaff-rigged sail. He sailed this boat on Lough Dan, close to Glendalough, and he and his brother Henry used to take friends for a sail in the Water Wag. Bigger and better boats followed: by 1895 he was taking the half-deck "Marguerite" across the Channel and in 1897 there was a long cruise to the Frisian Islands, Norderney and the Baltic with Henry in the thirty-foot cutter "Vixen": a voyage he repeated in the following spring.