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Samuel Pepys observed that the Romans had built coastal forts as ‘guards to their ships and not their ships to them’, and that modern historians ‘familiarly’ called ships ‘floating castles’ (a metaphor used by John Evelyn in his discourse on timber). Pepys made a note to investigate ‘when that phrase appears to have been taken up first’. For Walter Raleigh, ships were ‘His Majesty’s many movable forts’, and Elizabeth’s chief advisor, William Cecil, saw the fleet as ‘the wall of England’. During the century of English overseas expansion between Raleigh and Pepys, the defensive architectures of sea and land were intimately related. This paper will investigate their interaction in the process of English colonization in the Atlantic world, examining debates over their relative necessity and value. It will also consider the migration of building expertise between places and across disciplines in the colonial context.