The Hospitallers briefly acquired a few Caribbean islands (St Croix, St Barthelemy, and the French halves of St Martin and St Christopher) in 1653. France's governor of these islands since 1639, Philippe de Longvilliers de Poincy, was a knight of the Order and he had encouraged the Hospitallers to purchase them from France, extolling the profit that they could bring to the Order. When the Hospitallers bought the islands in 1653, de Poincy retained his position as governor. De Poincy had built sugar plantations and mills on the islands, particularly St Croix, and so they could be expected to bring a decent profit to the Hospitallers. However, the Order seems to have never been particularly enthusiastic about the venture. When de Poincy died in 1660, they considered selling the islands, worried that the Dutch or English might capture them. Also, the French West India Company had begun to make overtures to buy them back.
The Hospitallers commissioned a report to examine their options. It concluded that France's offer undervalued the islands, which the commissioners claimed were worth about six million livres. France continued to pressure the Order and the Hospitallers eventually relented, agreeing to the sale in 1665 in return for half a million livres, but the full sum was never paid and the brethren received just 100,000 of this amount.
This brief foray into the Caribbean was driven more by de Poincy than the Order's leadership. With the governor dead, the project soon fell apart. There doesn't seem to have been any real plan on the Hospitallers' part to expand into the Americas. There were only two other attempts to bring the Order to the New World. in 1793, five years before their expulsion from Malta, the grandmaster was negotiating with the US for the Order to acquire lands for the brethren and the Maltese to settle in return for allowing the American ships to use Malta's harbours, but no agreement was reached over this. There was a plan to establish a priory in French Canada, but this also failed, though several members of the French administration there were knights of the Order, including Charles Huault de Montmagny, governor of New France from 1636-48.
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