Flintlock of Fire
This elaborately crafted flintlock of brass and polished wood does not function normally. Instead, it may be drawn and fired once per day to launch four "bullets" as meteor swarm.
Strong evocation; CL 17th; Craft Wondrous Item, meteor swarm; Price 61,200 gp; Weight 3 lb.

Gold Tooth of Charisma
This gold tooth replaces one of the bearer's own teeth, and requires a DC 15 Heal check to be fitted. It grants the bearer a +6 enhancement bonus to Charisma.
Moderate transmutation; CL 8th; Craft Wondrous Item, eagle’s splendor; Price 72,000 gp; Weight 2 lb.

Parchment of The Black Spot
This small piece of folded paper is marked with a simple black spot. The first creature to unfold the paper and look at the spot must save against bestow curse, after which the paper loses its magic (regardless of whether the save is successful or not). The nature of the curse is determined by the creator when the parchment is first enchanted.
Moderate necromancy; CL 7th; Craft Wondrous Item, bestow curse; Price 1,400 gp.

Pegleg of Punctuality
This wooden rod replaces one of the bearer's legs and requires a DC 20 Heal check to be fitted. It grants a +10 enhancement bonus to the bearer's base land speed and a +5 competence bonus on Balance checks. Wearing two such peglegs does not grant any additional bonuses; instead the bearer produces a distinctive rapid-fire staccato sound on a ship's deck (-10 penalty on Move Silently checks)*.
Faint transmutation; CL 10th; Craft Rod, longstrider; Price 10,000 gp.

Pirate Captain's Hat
This black triangular hat bears golden tassels, a red headband, and a white skull-and-crossbones symbol. It grants the bearer a +15 competence bonus on Intimidate checks.
Faint necromancy; CL 1st; Craft Wondrous Item, cause fear; Price 22,500 gp.

Pirate's Eyepatch
This black or crimson silk eyepatch is sewn with golden thread and worn over one of the bearer's eyes (regardless of whether or not that eye is blind). It grants the bearer darkvision out to 60 feet, low-light vision, and the benefits of the Blind-Fight feat. If the bearer already possesses darkvision or low-light vision, the effective range of those abilities is doubled. If the bearer already possesses the Blind-Fight feat, he gains blindsight out to 30 feet instead.
Faint divination; CL 1st; Craft Wondrous Item, true strike; Price 10,000 gp.

Pirate Queen's Finery
This vest and coat are ostentatious yet somewhat ragged, made from crimson silk or other fine cloth and adorned with lace and gold thread. They surround the wearer with an invisible but tangible field of force, granting her an armor bonus of +8, just as though she were wearing plate armor.
Moderate conjuration; CL 16th; Craft Wondrous Item, mage armor; Price 64,000 gp; Weight 6 lb.

Spyglass of Scrutiny
This spyglass functions as a normal spyglass, but also negates penalties to Spot checks due to distance, inclement weather, and other mundane effects.
Moderate divination; CL 9th; Craft Wondrous Item, true seeing; Price 4,500 gp; Weight 1 lb.

Other ideas:
-+1 keen cutlass
-Hook of Wounding (replaces one of bearer's hands)
-Jolly Roger ship's flag (morale bonus to all pirates on a ship, morale penalty to all crew on a target enemy ship)
-Ship's figurehead-dragon (or dragon turtle) breathes scorching ray, unicorn wards entire ship as magic circle against evil, kraken extends tentacles to grapple other ship, mermaid/siren charms enemy crew or uses control weather
-Pirate Queen's Chest - once buried binds the spirits of slain crew to guard it as incorporeal undead, warded against divination so can only be found by map

New Familiars (via Improved Familiar feat)
Prismatic Parrot-3HD magical beast, ranks in Bluff/Diplomacy and Perform, tongues ability, colour spray every 1d4 rounds by spreading its wings.
Undead Monkey-3HD undead, ranks in Sleight of Hand and Use Magic Device (and Balance, Tumble, etc.), no penalties to master if it's slain (simply revives the next night)

*All due credit to Terry Pratchett