The Gun Ketch by Dewey Lambdin

It's 1786, and Alan Lewrie has his own ship at last: the Alacrity. Small but deadly, the Alacrity prowls the waters of the Caribbean, protecting British merchants from pirates. But Lewrie is still the same old rakehell he always was. Scandal sets tongues wagging in the Bahamas as the young captain thumbs his nose at propriety and makes a few well-planned conquests on land before sailing off to take on Calico Jack Finney, the boldest pirate in the Caribbean.