Battle of Guadalquini

Castañeda's squadron set sail from Havana on the morning of 5 June 1742.

They carried on board numerous supplies, 600 regular troops and 700 militiamen, which were deemed necessary, as they were to join those already available to Montiano in San Agustín, 300 regular troops, the militia, plus the troops sent previously from Havana, 100 soldiers under the command of Gregorio de Aldana and 100 brown militiamen.

The troops were commanded by Lieutenant Colonel Francisco Rubiani, commander of the Italica Dragoon Regiment. Just over twenty ships arrived at St. Augustine on 15 June, where they met up with those who had been separated during the crossing, and arrived in port a few days earlier.

They disembarked provisions for the square and began to load water. These operations of transferring everything necessary for the campaign to the ships in boats and launches was delayed for many days by the strong winds, so that the squadron was not ready until the end of June. 

The Spanish contingent consisted of some 2,000 men, with a regiment of dragoons, two infantry battalions, which included a company of marine infantry from the Windward Armada, artillery, and the troops of St. Augustine, which consisted of six companies, two battalions of militia and six independent companies, including troops of free blacks and Yamasee Indians.

The 55 ships of the squadron set sail at 7 am on 1 July. They were joined by the ships already in St Augustin, six galleots, several transports and canoes.

In rough seas, the smaller ships, four galleots and several canoes, had to take refuge on the coast, and two other canoes had to be towed by the pingue San Lorenzo and the frigate Flecha.