Francis Drake tried to enter Santa Cruz harbour on November 3rd, 1585. This was after Drake was knighted and before the defeat of the Spanish armada. The Spanish regarded him as a pirate, with some justification.
Drake left Plymouth with 23 ships and over 2,000 men, heading for the Caribbean. The prevailing winds meant that the logical route was via the Canary islands, so he headed for the biggest port in the Canaries at the time – Santa Cruz de la Palma. He sent some of his fleet around the island to Tazacorte, to divide the Palmeran defence, but the defenders weren’t fooled.
As they approached, they came under fire from St Catherine’s castle (the one on the sea-front) although it seems that none of the shots hit. Then St Michael’s castle (the one on the hill) opened fire and Drake hurried left before his boat was sunk.
Ironically, it seems the canon which did the most damage was one that the island government had bought from the Tower of London. So yay for English engineers.