There was once a hobbit. This hobbit got tired of living the normal hobbit way. That is, living in close proximity to a race of the Biggers (except in the case of the Dwarves, who are simply the Slightly Biggers). This hobbit, named Ralph, decided to set sail. And so he got together a band of likewise minded hobbits, and the group came to the port city of Trop. They looked about for a ship to sail that was reasonably priced. Finding none such ship, what came next is best classified as a "misunderstanding." Ralph, captain of the hobbits, will swear up and down, on any god (preferably the god of lies, trickery, or deceit), that his crew, through no fault or purpose of their own, under no orders from him, cut off the ropes holding a ship to the dock and sailed away in the dead of night. The previous captain fails to see it that way. The next part of the story, all parties can agree upon. The evil (Ralph's adjective) captain hired another ship, and set sail after the hobbits. The evil captain then attacked Ralph's ship, boarded it, and quickly overcame the less strong hobbits. Ralph and his crew were marooned.
A lesser captain would have succumbed to death. But not Ralph. Because a hobbit is physically shorter than humans, they need less headspace. Thus, if they made a ship, it doesn't need to be so tall. Thus, they need less wood. The island that the evil captain marooned them on failed to have enough wood for a human ship. And so Ralph set to work. In a week (smaller construction time), the HAS Endeavor (the HAS stands for Hobbits Are Superior) set sail. Relying on luck, gumption, and sheer willpower, it failed to sink. It also failed to sink when the hobbits decided to borrow some supplies from that unarmed trading vessel. It also failed to sink when Ralph and the evil captain ran into each other in a bar, which developed into a naval battle. From there, the hobbits decided to rely on such things as nails, and all the other things that hold human ships together. And while they got those nails, they added 5 ballistae on each side, as well as a swiveling one. And from there, the hobbits have had a good, good time.
The HAS Endeavor:
The HAD Endeavor is a hobbit-sized sloop. It has 10 ballistae, with 5 mounted on each side, and a swiveling ballista mounted on the bow. It has three decks. The top has the ballistae and the captain's quarters. The second has the crew's hammocks and kitchen. The bottom has storage. About half of the storage compartments will usually consist of food and water (with water most of that), with the rest consisting of unsold loot, extra ballista ammunition, and weapons.
The hobbit crew consists of about 50 hobbits. The hobbits are typically armed with a cutlass, and two dirks. Some have other weapons, but cutlass/dirk/dirk combo is the norm. 30 man the ballistae, with the remaining 20 being rotated on duty. The crew also has 5 wizards, whose main duty (outside of battle) is creating a constant, favorable breeze, which is why no hobbit ever has to row, or why they don't have slaves. The crew are devoted to Ralph, because he has so far led them true towards adventure, fun, and loot.
Ralph's main goal in life is to have fun. He enjoys sailing the world, looking for adventure, money, and unarmed merchant trading vessels stock full of supplies that should be his. He should be played as such. He uses the usual weaponry of his crew. He will sail wherever his fancy takes him, though he will usually be found around archepeligoes and major shipping routed.