The point where Philip was now to feel the weight of his arm was the fair city of Santo Domingo in Española. It was by far the most serious operation Drake had yet undertaken. Hitherto his exploits had been against places that were little more than struggling settlements, but Santo Domingo was indeed a city, stone-built and walled, and flanked with formidable batteries. It was held by a powerful garrison, as Drake learned from a captured frigate, and a naval force had been concentrated in the harbor for its defence. As the oldest town in the Indies, its renown had hitherto secured it from attack, and in Spain it was held the queen city of the colonial empire. The moral effect of its capture would be profound, and, besides, from Virginia the governor of Raleigh's new colony had sent home a fabulous report of its wealth. Drake was fully alive to the gravity of the task before him. His dispositions had never been so elaborate, and they evince at least a touch of that military genius which the strategists of the next century denied him. While the sick were recruiting he sent forward a squadron to reconnoitre, and, if possible, to open communications with the maroons who infested the hills. For three days the garrison was thus exhausted with constant alarms, and then on January 1, 1586, the whole fleet appeared in the bay.

Night fell, and, as darkness closed the eyes of the harassed garrison, with the fleet all was activity. In boats and pinnaces the troops were being rapidly embarked, and soon Drake in person was piloting the flotilla for the surf-beaten shore. At a point within the bay, but some ten miles from the town, a practicable landing-place had been found. Watch-houses overlooked it, but watchmen there were none. Drake had got touch with the maroons. By his directions a party of them had stolen down from the hills, and as the sentries came out from the city in the evening, swiftly and silently they had been every one despatched. Thus, unseen and unmolested, the troops were successfully landed, and then, with pious and cheery farewells to Carleill, Drake returned to the fleet to prepare the ground for the surprise.

In the morning he anchored in the road, ran out his guns, and proceeded to threaten a landing at a point close to that side of the town upon which Carleill was stealthily approaching in two parallel columns. As the Spaniards saw the fleet preparing the advance of the boats and pinnaces, the whole of the horse and a large force of foot marched out of the town to oppose the threatened attack, and took up a position fronting the sea, with their left resting on the town and the other flank exposed in the line of Carleill's advance. It was exactly what had been foreseen, and, ere the Spaniards had discovered that the movement from the fleet was merely a feint, the horse which were covering their exposed flank were flying before Carleill's musketeers.

The surprise was complete. Taken in flank by Carleill, and threatened in the rear by his second column under Powell, the chief of the staff, the infantry could make no real resistance; and so rapidly was the English advance pushed home that the struggling mass of friend and foe entered pell-mell through the open gates of the town. For an hour, alarms of drum and trumpet mingling confusedly with the sounds of street-fighting reached the listening fleet as the two columns forced their way to meet upon the Plaza. But how they fared none could tell, till on a tower a white staff suddenly appeared, and in another moment the cross of St. George fluttered gayly out upon the breeze. With a roar of triumph the ships' guns saluted the signal of victory. The town was won.

Though the garrison fled panic-stricken across the river on the far side of the city, and the citadel was evacuated in the night, the place was far too large to be occupied by the force at Drake's command. Following, therefore, the same tactics that had been successful at Nombre de Dios, he ordered the troops to intrench themselves in the Plaza and to occupy the principal batteries. In this way he held the city for a month. The plunder was disappointing. The city was already a hundred years old, and its day was done; for the reckless native policy of the colonists had almost ruined the island. It remained but to treat for a ransom. The Governor at once declared himself unable to meet the extravagant demands of the English admiral, and in order to bring him to terms Drake began to burn the town piecemeal. But so well was it built that little harm could be done, and every day his impatience increased.

Once, in the course of the negotiations, he sent a boy with a flag of truce to the Spanish camp. A Spaniard, meeting the lad, so ill-treated him that he could barely crawl back to die at the admiral's feet. Then all the fury of Drake's nature burst forth. Two friars who were among the prisoners were immediately sent ashore and hanged by the provost-marshal on the scene of the crime. Another was despatched to the Spanish camp to declare that two more would be executed every morning until the offender was brought down and hanged on the spot by his own authorities. In hasty alarm the demand was complied with, and then the international dinners and the negotiations went on more smoothly. Convinced at last of the poverty of the colony, Drake accepted a ransom of twenty-five thousand ducats. The sum, which is equal to about fifty thousand pounds of our money, though little enough to satisfy the shareholders, was very serious for the enemy. For besides this loss the town had been stripped of everything worth carrying away by the troops and seamen. Two hundred forty guns were taken on board the English ships; and not only were they thoroughly refurnished from the Spanish stores, but for a month the whole expedition had lived in free quarters at the enemy's expense. The entire fleet which lay in the harbor fell into Drake's hands, and, with the exception of four of the finest galleons, was given to the flames. Besides the vessels which the Spaniards themselves had scuttled, two galleys with their tenders, fifteen frigates, and a galleon were thus destroyed, and hundreds of galley-slaves set free.

"It was such a cooling to King Philip," said one in Europe as the news leaked out, "as never happened to him since he was King of Spain." But as yet Drake was far from done. In the middle of February, with his force recruited by the English prisoners he had freed, and with a troop of attendant prizes laden with his spoil, in undiminished strength he appeared before Cartagena. No city in America was more difficult of approach, but the memories of the old hard days were still green, when, storm-beaten, drenched, and chilled, without food or shelter, he had ridden in the harbor day after day in despite of all the Spaniards could do, and he knew it all like a pilot. The city was built close to the shore fronting west, and directly from its southern face an inlet of the sea stretched many leagues southward along the coast, forming a large lagoon. The long spit of land which separated this sheet of water from the sea was pierced by two natural channels. At the far end was the dangerous Bocca Chica, and some three miles from the city was a larger entrance known as the Bocca Grande. Between this entrance and the town a tongue of land ran out at right angles from the spit to the opposite shore, forming an inner harbor and barring all approach to the city from the outer part of the lagoon, except by a narrow channel which lay under the guns of a powerful fort on the mainland.

On its northern and eastern faces the city was encircled by a broad creek, which ran round it from the inner harbor to the sea in such a way as to form a wide natural moat, rendering the city unapproachable from the mainland except by a bridge. This bridge was also commanded by the harbor fort, nor were land operations possible at any other point except from that part of the spit which lay between the city and the Bocca Grande. So finely, however, did this narrow down before the city could be reached, that between the inner harbor and the sea it was but fifty paces wide, and here the Spaniards had had time to prepare defences that looked impregnable. From shore to shore a formidable entrenchment completely barred the way; and not only was its front so staked and encumbered as to render a night attack impossible, but its approaches were swept by the guns and small-arms of a great galeas and two galleys which lay in the inner harbor.

To a man so tender as Drake ever was for the lives of his men and the safety of his ships, to attack such a place might well have appeared hopeless; but the originality of the amphibious corsair at once descried a hole which had escaped all the science of the Spanish martialists. Instead of entering by the Bocca Grande, with consummate skill and daring he piloted the whole fleet through the dangerous channel at the extreme end of the lagoon. The only impression which so hazardous a movement could create in the minds of the Spaniards was that he was about to repeat his Santo Domingo operations, and land his troops there to attack from the mainland. Such an impression must have been confirmed as, moving up the lagoon, he anchored opposite the Bocca Grande and threatened the harbor fort with his boats; but Drake's project was far different. Instead of being landed on the mainland, Carleill with eight companies was quietly slipped ashore in the Bocca Grande, with instructions to make his way diagonally through the woods that covered the spit till he reached the seashore, and then, instead of advancing on the front of the intrenchments, to wade along through the wash of the surf till he was within striking distance of the Spanish position.

Meanwhile Frobisher advanced with the flotilla against the harbor fort, and as soon as Carleill was heard in contact with the enemy's pickets he opened fire. The boat-attack was repulsed—indeed, it may only have been intended as what soldiers then called "a hot alarm"—but Carleill was completely successful. By the march through the surf he had not only evaded the obstacles which the enemy had so carefully prepared, but he had been covered from the fire of the galleys in the harbor, and had never so much as entered the fire-area of the heavily armed intrenchments. After a desperate struggle at push of pike, the position was carried by assault, and once more so hotly was the advantage pursued that in one rush the whole town was captured. The garrison fled across the bridge to the hills, and the next day, when Drake brought up the fleet to bear upon the fort, that also was evacuated.