Jack Sparrow from "Pirates of the Carribean":
Edward Kenway from "Assassin's Creed IV: Black Flag":
Incognito from "Sid Meier's Pirates! (2004)":
Captain James Flint from "Black Sails":
Sinbad the Sailor from "Sinbad: Legend of the Seven Seas":
All Characters are in their primes, with their best equipment, although none will have access to supernatural elements. In the case of Incognito, he is using the Perfectly Balanced Rapier, and is wearing a Silk Fencing Shirt, as well as his Brace of Pistols, with his main skill being chosen as "Fencing".
Edward Kenway is using the Pirate Scimitars and Gold Flintlock Pistols, and is wearing the Pirate Captain outfit, along with all his upgrades.
The rest don't need explaining as they're from movies and TV and have an equipment standard.
Round 1: Sword Duel
Round 2: Gun Fight
Round 3: Ship Battle
Round 4: Ship Battle, but boarding is allowed/Anything Goes