The original war plan had called for landing the US Army’s Fifth Corps at the northern Cuban port of Mariel. But the appearance of Admiral Pascual Cervera y Topete’s cruiser squadron in Santiago harbor on the south Cuban coast changed all that. After reaching Cuba and meeting with his counterparts in the U.S. Navy and the Cuban rebel command, Fifth Corps commander General William Shafter decided to land his troops at the hamlet of Daiquiri. Situated sixteen miles east of Santiago where the Navy now had Cervera blockaded, Daiquiri was an iron mining hamlet with no harbor and just one dock used by ore transports. That made for a slow landing by boat, after which the troops discovered that the “Camino Real” (“royal road”) which the maps said ran from Daiquiri to Santiago actually resembled “the roughest mountain roads in the southern part of our own Appalachian Mountains.” Nevertheless, Shafter was determined to send a force inland quickly, as he was concerned that any delay would put his troops in danger of being decimated by yellow fever.

While General Henry Lawton’s infantry headed up the road to the coastal town of Siboney, Shafter’s deputy commander Gen. Joseph “Fighting Joe” Wheeler rode ahead of them and discovered a Spanish force massing on a ridgeline at Las Guasimas. Though ordered by Shafter to stay behind and oversee the Daiquiri beachhead, the ex-Confederate cavalry commander instead ordered Brigadier General Samuel Young’s 2nd Cavalry Brigade out of Daiquiri and up the road to attack the Spanish position the next morning. The cavalrymen would be going into battle on foot, as poor planning had resulted in most of their horses being left behind in Florida.

Major General Arsenio Linares had allowed the Americans to land at Daiquiri unopposed, and then withdrew his forces from the coastal region as the Americans advanced to Siboney. His rather unconvincing explanation to his troops was that he did not want to sacrifice their lives to American naval gunnery fire. But at Las Guasimas he formed a strong defensive position, with his forward line on the ridge and two more lines in reserve farther west. Cuban rebel attacks on his forward line were brushed off with ease, but soon Linares became concerned that the American infantry to the south under Lawton would march westward along the coastal road and then cut northward behind him to attack Santiago. So obsessed was he with this idea that by the morning of the American attack, Linares had already issued the order to withdraw from Las Guasimas. The commander on the scene, Brigadier General Antonio Rubin, sent some of his reserves forward to reinforce the line on the ridge but then prepared to evacuate the rest of his troops. As a result, the American attack fell on only a fraction of the total Spanish force, which pulled up stakes and retreated with the rest of the Spaniards after only two hours of fighting. The Americans (who were utterly unaware of the Spanish retreat plan) claimed the battle as a great victory, while the Spanish deemed it a successful rearguard action. In any event, the front-line Spanish troops joined their comrades in the retreat to Santiago as the exhilarated but exhausted Americans consolidated their position.