On the 20th of December 1654 Rear-Admiral Dakins was sent on with fourteen ships in advance. The bulk of the expedition sailed on Christmas Day, which was probably chosen at least partly from a Puritan desire to show disrespect for the feast. In mid-ocean the heavier ships, which hampered the speed of the fleet, were left behind. Penn and Venables pressed on with the better sailers. By the 29th January 1655 the whole armament was assembled in Carlisle Bay in Barbadoes.
The disappointments of the expedition began at once. It was found that those planters who had been urging the Government to send a force into the West Indies, and had promised effectual help, had spoken without authority. The planters of Barbadoes were by no means generally pleased at the appearance of an expedition from England. The generals were authorised to raise a regiment in the island, and the planters were afraid that if the freemen enlisted in large numbers, their "servants" would revolt so soon as the armed force was gone. By servants must be understood both the black slaves and those white men, criminals and prisoners of war, who were bound to a term of service. Much pressure had to be exercised before this opposition was overcome. It was at last surmounted, and the regiment was raised. In the meantime the news spread through the English islands. The swarm of loose adventurers who filled them, the runaway "servants," sailors who had deserted from their ships,--all the raw material, in fact, out of which the formidable buccaneering body called the "Brethren of the Coast" was afterwards formed,--began to collect in regiments, and were burning to take part in the service, which seemed to promise plunder. Such men as these, the floating population of the frontier, valiant in pothouses, but feeble in battle, were of no real value for military purposes. Yet they were accepted to the number of several thousands. The expedition had unfortunately been put under the command of a committee. In this Cromwell followed the practice of the Parliament, and was perhaps influenced by the fear of putting too much power into the hands of a single man. Not only Penn and Venables, but Goodson the vice-admiral, Dakins the rear-admiral, two special Commissioners, Winslow and Gregory Butler, together with some others, were joined in the general command, and nothing was to be done without the consent of three of them. The opinion of the wiser few, who would willingly have dispensed with the riff-raff of the islands, was overborne, and the expedition was hampered by an ill-armed, worse-disciplined, and thoroughly untrustworthy mob. It is to be noted also that this distant and unhealthy service in the West Indies was not popular with the sailors. While at Carlisle Bay, the sea officers came in a body to Penn and represented to him their hope that the hardships of their service would be allowed for in their pay and prize-money. One good measure that had been decided upon in England was here perfected. A regiment of sailors was formed. It was put under the command of Admiral Goodson as colonel, with naval officers to lead the companies.