The Spanish forces expected the Americans to attack the northern region of the island and concentrated their defenses around San Juan and Arecibo. The Spanish government was also aware of a planned landing by the Americans in Fajardo, located on the east coast and had that city fortified. However, the southern and western regions of Puerto Rico were left with little or no defenses at all.
After Cuba was taken, President McKinley approved the land invasion of Puerto Rico by way of Fajardo, taking into consideration that the Spaniards had fortified San Juan, where they expected the initial attack. A convoy of ships left Tampa, Florida and on July 21 another convoy, which included the USS Yale, USS Massachusetts, USS Gloucester and the USS Dixie, departed from Guantánamo for a 4 day journey to Puerto Rico.
Major General Nelson A. Miles, Commanding General of the Army, was aboard the USS Yale. While approaching the Strait of Mona of Puerto Rico, Miles opted to land his troops in the southern region of the island, picking Guánica as his landing zone. He sent patrol boats to notify all other convoys of his decision and order them to join him. His decision was based on his belief that the city of Fajardo would be fortified and he feared that small gun boats based on the shore could disrupt a landing there.
On July 25, Miles and a convoy of ships, under the command of Naval Captain Francis J. Higginson, arrived at Guánica Bay. The following troop carrying ships were part of the convoy: USS Yale with Generals Miles and Garretson, plus 1,300 infantry soldiers of the 3,300 total that were assigned for the initial invasion, USS Columbia, USS Lampasas, USS Windom, USS Comanche with General Guy V. Henry, Nueces, USS Unionist, USS Stillwater, Rita and USS Specialist (both the Nueces and the Rita were Spanish ships which were confiscated by the Yale). These ships were accompanied by the following battleships, destroyers and cruisers: the flagship USS Massachusetts, USS ...