For the little raider we recommend Small Saul by Ashley Spires. Can Small Saul prove his worth to his pirate crew or will he be forced to walk the plank?
For the bigger swashbuckler we recommend Pirate Latitudes by Michael Crichton. A Spanish galleon full of gold is always a perfect pirate target.
On Stranger Tides by Tim Powers. No this one is not part of the Pirates of the Caribbean movies but it is about pirates, Blackbeard to be specific. If that isn't enough there is the search for the fountain of youth (apparently this is a popular pirate quest) and also Zombies.
We have plenty more titles to recommend, but if you are feeling a little lost at sea may we recommend brushing up on your pirate speak. Our Mango languages database includes a complete course in Pirate. You will learn everything from how to give sailing commands, to greeting your boss, or calling someone names.
Our history database also carries Piratepedia an e-book that has information on ships, hideouts, adventures, and even some gnarly pirate endings. Now you should have all you need to be a buccaneer of the seven seas.
Fair winds, me hearties.