In the early modern world expertise and skill paved the way to position and fame. Knowing how to do things, be it build, explore or navigate, could ensure a position at court and win financial backing. This talk will introduce George Waymouth, captain and explorer, ship builder and city designer, military engineer and author. His diverse and highly desired skills won him favour in the late Elizabethan and early Stuart court. Among his own writings is a lengthy and little studied manuscript, The Jewell of Artes (1604), that testifies to Waymouth’s expertise in all of the skills required for a captain of a ship and the leader of a colony in the new world. Waymouth deserves to be better known not only as one of early colonists of the North Virginia colony along the coast of what is now Maine but also for knowledge of what might be called skills allied to the arts of architecture, urbanism and engineering. Shipbuilding, as with the military and navigational arts, was closely connected with architecture in all of its forms. Waymouth’s colourful career, well documented on two continents, gives some indication of the knowledge of these worldly characters and how they sought to exploit what they knew.