Karajan had been sailing since he was a boy and in 1938 he bought his first yacht, the "Karajanides". In 1967 the first "Helisara" was launched, the name of the boat being an acronym of (H)erbert, (El)iette, (Is)abel and (Ara)bel.

There were five more boats bearing this name ending with the maxi racer, "Helisara VI". This yacht, which was 79 feet long by 17 feet wide and whose mast was 98 feet high, won Karajan several regattas.