After the declaration of war in April, the Spanish fleet was quickly sent to Cuba under Admiral Pascual Cervera. The ten boats in Cervera's command were in truly horrible condition. Of the 10 rotting ships, only 7 actually made it to Cuba. The other 3 had to be abandoned along the way. Despite the rather pathetic nature of the Spanish fleet, Americans on the Eastern seaboard became very frightened of a potential Spanish invasion of the US. Eventually, Cervera's decrepit fleet limped into Santiago harbor in Cuba, where they were blockaded by the US Navy.
With the Spanish fleet contained, the US planned a landing of the US Army, which would then attack the Spanish from the rear. The landing was made under the command of General William R. Shafter, a veteran of the Civil War. Shafter was so fat and ill with gout that his men had to carry him around on a door; he matched that dubious physical condition with an uninspiring talent at logistics and strategy. The US had absolutely no experience fighting in the tropics, and the unprepared US Army showed up in Cuba with vast supplies of wool clothing.
Better equipped for the job in Cuba were the famous "Rough Riders", a ragtag group of volunteers fighting for the US. Most of them were cowboys, but all kinds of colorful characters, from the wealthy thrill-seekers to former criminals, found their way into the unit, which was commanded by Colonel Leonard Wood. The Rough Rider officer best remembered, however, was no doubt Lieutenant Colonel Theodore Roosevelt. Roosevelt, ever a fan of strenuous activity and competition, had resigned his post as Assistant Secretary of the Navy to fight in the war. Roosevelt had absolutely no military experience, and the military had even had to bend some rules to let him in with his terrible nearsightedness. Keeping enough glasses on hand for Roosevelt, so he could still see if the ones he was wearing broke, was a difficult task.
US forces landed at Santiago without having to fight the Spanish, as the Spanish proved even more confused than the Americans. On July 1, 1898, the first major land battles of the war were fought at El Caney and at San Juan Hill. The Battle of San Juan Hill was famous because the "Rough Riders", walking since many of their horses did not arrive in Cuba, charged up the hill. The battle was soon immortalized in a Frederic Remington painting (mentioned earlier in the Commentary on Yellow Journalism. The US won both battles, though the "Rough Riders" suffered heavy losses. Roosevelt, for his part, enjoyed himself immensely, and even shot a Spanish soldier. These battles proved decisive.
Now that the war was almost over, the US quickly moved to occupy Spanish-owned Puerto Rico. On August 12, 1898, the Spanish signed an armistice ending the fighting.
Despite the "Rough Riders" famous legacy, both they and the US Army were so disorganized and bumbling that only about half of them made it from Tampa Bay, Florida to the landing at Santiago. And although the "Rough Riders" were organized as a cavalry unit, very few of their horses actually made it to Cuba. As a result, most of the "Rough Riders" actually walked during the war. That the war went so well for the US was virtually a miracle given the disorganization and poor planning that plagued the American military effort.