The regiment trained for several weeks in San Antonio, Texas; in his autobiography, Roosevelt wrote that his experience with the New York National Guard enabled him to immediately begin teaching basic soldiering skills. Diversity characterized the regiment, which included Ivy Leaguers, athletes, frontiersmen, Native Americans, hunters, miners, former soldiers, tradesmen, and sheriffs. The Rough Riders were part of the cavalry division commanded by former Confederate general Joseph Wheeler. Roosevelt and his men landed in Daiquirí, Cuba, on June 23, 1898, and marched to Siboney. Wheeler sent the Rough Riders on a parallel road northwest running along a ridge up from the beach. Roosevelt took command of the regiment; he had his first experience in combat when the Rough Riders met Spanish troops in a skirmish known as the Battle of Las Guasimas. They fought their way through Spanish resistance and, together with the Regulars, forced the Spaniards to abandon their positions.thumb|Colonel Roosevelt and the Rough Riders along with members of the 3rd Volunteers and the 10th Cavalry Regiment after capturing Kettle Hill in Cuba during the Spanish-American War in July 1898 On July 1, in a combined assault with the Regulars, under Roosevelt's leadership, the Rough Riders became famous for charges up Kettle Hill and San Juan Hill. Roosevelt was the only soldier on horseback, as he rode back and forth between rifle pits at the forefront of the advance up Kettle Hill, an advance that he urged despite the absence of orders. He was forced to walk up the last part of Kettle Hill because his horse had been entangled in barbed wire. The assaults would become known as the Battle of San Juan Heights. The victories came at a cost of 200 killed and 1,000 wounded.
the regiment trained for several weeks in san antonio texas; in his autobiography roosevelt wrote that his experience with the new york national guard enabled him to immediately begin teaching basic soldiering skills diversity characterized the regiment which included ivy leaguers athletes frontiersmen native americans hunters miners former soldiers tradesmen and sheriffs the rough riders were part of the cavalry division commanded by former confederate general joseph wheeler roosevelt and his men landed in daiquirí cuba on june 23 1898 and marched to siboney wheeler sent the rough riders on a parallel road northwest running along a ridge up from the beach roosevelt took command of the regiment; he had his first experience in combat when the rough riders met spanish troops in a skirmish known as the battle of las guasimas they fought their way through spanish resistance and together with the regulars forced the spaniards to abandon their positionsthumb|colonel roosevelt and the rough riders along with members of the 3rd volunteers and the 10th cavalry regiment after capturing kettle hill in cuba during the spanish-american war in july 1898 on july 1 in a combined assault with the regulars under roosevelt's leadership the rough riders became famous for charges up kettle hill and san juan hill roosevelt was the only soldier on horseback as he rode back and forth between rifle pits at the forefront of the advance up kettle hill an advance that he urged despite the absence of orders he was forced to walk up the last part of kettle hill because his horse had been entangled in barbed wire the assaults would become known as the battle of san juan heights the victories came at a cost of 200 killed and 1000 wounded