Discovered in 1993 at the mouth of the Tagus River, the SJB2 shipwreck-or 'Pepper Wreck'-was tentatively identified as the Portuguese Indiaman Nossa Senhora dos Mártires , lost on its return voyage from Cochin, India, on 14 September 1606. Following archaeological excavation and a tentative reconstruction of the ship's hull and rigging, the next step is the study of its structural strength and sailing characteristics using the tools of modern naval architecture. This paper presents a methodology for investigating the sailing and structural characteristics of the 'Pepper Wreck', combining archaeological, iconographic and contemporary written sources with modern naval architectural calculations.