Due to a combination of listening to some of @jewishdragon‘s sea shanties and reading Xanathar’s, I decided to build myself a pirate by combining the Bard College of Swords (swordplay and shanties for my spellcasting focus, natch) and the Rogue Swashbuckler Archtype, and of course Sailor Background.
I’m liking how this looks: I’ve got some really fun combat potential with Booming Blade, Blade Flourish, Fancy Footwork, and Rakish Audacity, I’e got Vicious Mockery for the Curse of Monkey Island style points, Expertise in Acrobatics and Stealth for whether I want to be flashy or sneaky, and the classic Bard spells.
The only thing remaining is picking my character’s race, and Tiefling just fits too well…
At which point I realize that I’ve basically reverse engineered Nightcrawler.
Now all I need to do is get a DM to agree to let me use Misty Step as one of my Tiefling Infernal Legacy spells and I’m set.