A Little Off The Top

 is the first quest given by the Innkeeper and the second quest in the Main Quest line.

Quest Dialogue
Beginning the quest:

Turning in the quest:

Walkthrough
To begin the quest, talk to the Innkeeper and choose Helping the Innkeeper. He will explain that pirates have stolen his favorite hat, and that he wants it back.

Upon accepting the quest, you'll now have the opportunity to ask for both the Innkeeper's Sword and a Sextant. If you talk to the Innkeeper again, you'll have the following dialogue options that will give you the latter two items:

To acquire the Innkeeper's Sword:

To acquire the Sextant:

The Innkeeper's Feathered Hat drops from any common pirate. Simply sail to a Pirate Island and kill a few as it has a very high drop rate.

Return to any Innkeeper upon acquiring the hat to turn in the quest.

Rewards

 * Ability to ask the Innkeeper for directions to the closest Merchant.
 * Access to the next quest in the questline, A Hat For A Hat.