Captain (Sea)Strider

Dirty Fighting: (2/short rest) If his attacks hit the enemy, he can choose as a bonus action to trip or disarm the target, the enemy creature must make a DC 15 strength save or he is disarmed or knocked prone. 

Sea Prowess: He has advantage on acrobatics and athletics checks that involve movement on a ship and in swimming checks.

Track Ship: The Captain speaks the name of a ship anywhere on the same plane of existence, and is able to know its location, the direction its traveling, and the current captain of the ship. Once per long rest. 

 Spellcasting. Capt. (Sea)Strider is a 3rd-level spellcaster. His spellcasting ability is Charisma (spell save DC 16, +7 to hit with spell attacks). Capt. (Sea)Strider has following spells prepared: 

Cantrips (at will): Sword Burst, Mending, Toll the dead.
1st level (3 slots): Inflict Wounds, Charm Person, Dissonant Whispers
2nd Level (2 Slots): Misty Step, Mirror Image,

Tool Proficiency: Vehicles(water), Thieve's tools, woodcarver's kit. 

Multi-attack.The Pirate makes two weapon melee attacks with his cutlass or one attack with his cutlass and the other with his light pistol.

Cutlass. Melee Weapon Attack +7 to hit, reach 5 ft, one target. Hit: 8 (1d8 +4) slashing damage. Properties: Finesse, Light.

Light Pistol. Ranged Weapon Attack +7 to hit, range 80/320ft, one target. Hit: 8 (1d8 +4 ) piercing damage. Properties: Ammunition: range 80/320ft.

Hook Hand (Bonus Action)  Melee Weapon Attack +7 to hit, reach 5 ft, one target. Hit: 6 (1d6 +4) slashing damage. Properties: Finesse, Light, Special (Hook hand cannot be disarmed in combat). A creature successfully hit with the captain's hook, must make a DC 14 constitution saving throw or to 1d6 poison damage and become poisoned for 1d4 rounds. 

Hook-n-Pull. (1/short rest) When an enemy creature hits you with an attack, you use your hook as a last second defense to impose disadvantage. If the attack misses, the enemy creature is then pulled to any space adjacent to you within a 5ft range. 

Chug Grog- On intitiative count 10, the Captain can use its legendary action to swig a jug of Grog, healing him for 1d6+3.