Transferring cargo at sea is dangerous at best. The smugglers usually rendezvoused with the merchants at small islands or isolated coves along the Canadian coast. Although more distant, the harbor at La Habana suited their purposes even better. Firstly, it had the Spanish to enforce neutrality and keep the British warships at bay. Secondly, the prevailing winds in the Caribbean favored the smugglers' craft over the British warships patrolling just outside La Habana.
The tradewinds in the Caribbean blow from east to west. A sailing vessel attempting to run from La Habana to the tip of Florida must sail against them. Thus, the smugglers could easily outsail British warships. Conversely, when sailing with the wind towards La Habana, the smugglers spread their square sails and raced ahead of the warships to the Spanish sanctuary.
Cubans welcomed the Yankees. To them, the Yankees brought the same kind of commercial success that they had enjoyed during the brief period when Britain occupied the island. Both peoples welcomed the profits and were equally disappointed when the American Revolution ended, and Spain once again closed La Habana to all foreign trade.