ON JUNE 3, 1898, 39 days into the Spanish-American War, Theodore Roosevelt and his Rough Riders arrived in Florida by train, assigned to the U.S. transport Yucatan. But the departure date from Tampa Bay for Cuba kept changing. Just a month earlier, the 39-year-old Teddy had quit his job as assistant secretary of the Navy, taken command of the 1,250-man 1st Volunteer Cavalry Regiment along with Leonard Wood, and began a mobilization to dislodge the Spanish from Cuba.

Roosevelt worried that if the ship didn’t leave soon, his men’s livers weren’t going to withstand all the booze they were consuming. The first day was incredibly humid, with a hot, glassy atmosphere and scant wind. Anxious for war, Teddy was unperturbed by the omnipresent swarms of chiggers and sandflies. To kill time he studied Florida’s botany, learning to distinguish lignum-vitae (holywood) trees from blue beech and ironwood at a glance.