Increasing numbers of English sailors were drawn to the Caribbean Sea from the 1550s onwards. The approach was that which was pioneered by Columbus in his first voyage, exploiting the wind system in the North Atlantic. The prevailing wind circulates around the North Atlantic, blowing vessels south from Britain and Western Europe and then westwards – the suitably named trade wind – towards the Caribbean; as a consequence the ocean currents set the same way, and in particular a major current driven by the trade wind thrusts sailing ships towards the line of the Windward Islands.

The Caribbean could be entered only from the east. The way lay through several straits between the innumerable islands, but it was normal to enter by the Straits between a few of the Windward and Leeward Islands (also called the Lesser Antilles), particularly at the southern end of that island chain, past Barbados and Dominica, or perhaps by Antigua or St Kitts at the northern end. From there ships were assisted by the current which circulated round the Caribbean.

Sailing ships heading from Western Europe to Central or North America therefore sailed south to the Canary Islands, then west to and past Barbados or Dominica, or one of the other islands, and dispersed from there to their various destinations. This route took advantage of the steady trade wind, and of its current, which could move the ship onwards even if the wind failed. Returning towards Europe, ships from ports in the Caribbean sailed north through the Yucatán Passage and then past Cuba to the Florida Passage between Cuba and Florida; if they could, they might pass through the Windward Passage between Cuba and Hispaniola; both streams of traffic then headed north between Florida and the Bahamas helped by the Gulf Stream, until they picked up a westerly wind.

These voyages might take a long time, depending on wind and currents, but a British Navy ship in the eighteenth century sailed west to east from Jamaica to London in five weeks; it had taken eight weeks on the voyage out. Merchant ships normally took much longer, in both directions.