Having undertook naval expeditions to the coasts of Spain in 1587, 1588 and 1589, in the spring of 1591, the Earl of Cumberland sailed to Cape St. Vincent in a new privateering campaign with one royal ship, the 600-ton galleon Garland, and four of his own, the 260-ton Sampson, the Golden Noble, Allegarta, and the small pinnace Discovery. Sir William Monson of Stuart, later Admiral of the Royal Navy, was his second in command. Off the Spanish coast they took a pair of Dutch ships sailing from Lisbon with spices. Though the Dutch Republic was allied with England against the Spanish Crown, the ships took by the English squadron had on board goods of Portuguese merchants.