This is the set list for Episode 564: Free To Ask Question which originally aired on July 19, 2023 and can be heard here.
- Ye Banished Privateers: Welcome To Tortuga; Songs and Curses
- Shank Painters: Down Among the Dead Men; Shank Painters
- Dan Zanes & Festival Five Folk: Strike the Bell; Sea Music
- The Roving Blades: Mary Ellen Carter; And Now We’re Anchored
- Scott Jeffers Traveler: Calico Jack (Rackhams Reel); Mutiny
- Port O’Thority: Castillo Straits; Hooke, Line, & Sink Her
- Ye Banished Privateers: Mates Together; Mates Together – Single
- Brigada Pirata: Captain’s belief; Black Sam The Prince of Pirates
- Five Pint Mary: Tell Me Ma; Five Pint Mary
- The Dreadnoughts: We Shepherds Are the Best of Men; Green Willow
- O’Craven: Borrowed Time; The Lady Luck Tour EP
- Captain Hellfire and The Wretched Brethren: On Our Knees; Captain Hellfire & The Wretched Brethren
- Capt’n Tor & the Naer-Do-Well Cads Pirate Invasion: A Bold Decision; Fanny
- The Langer’s Ball: Place to Lay My Head; Hold Tight
- Blaggards: Botany Bay (Live); Live in Texas
- Captain Dan & the Scurvy: Crew Derelict; Rated Arrr
- The Bilge Pumps: The Old Black Rum; Planned Piratehood
- Musical Blades: Young, Dumb, and Full of Rum; Heads, Hearts & Tales
- Highland Reign: Raise Your Glasses; Seven White Ponies
- The Pirates Charles: Raise the Whiskey High; Conquer
- Alestorm: Wenches & Mead; Captain Morgan’s Revenge
- Wakefire: The Fisher and the Siren; Midnight Circus
- Hornswaggle: Tallulah’s House of Delights; Heart, Soul and Blood
- The Minstrel Rav’n: Bawdy Song; The Purple Headed Monster
- The Dread Crew Of Oddwood: Brothel Royale!; Heavy Mahogany
- potcheen: Likker; Take No Prisoners
- The Harlot Queens: Blow the Man Down; Does a Bawdy Good
- Friar Finnegan: You know I love to feel up my woman; Please don’t play this one for the kids
- Chaste Treasure: Desperate; Slippery When Wit
- Ménage à Moi: Give it to Mary (with Love); Raise a Toast
- Opal & Jade: S-L-U-T; Sorry Not Sorry
- The Cannibal Tudors: Boobies; Z Day In New Market Village
- Iris & Rose: The Captain’s Wife’s Lament; Knees Up!
- The Harlot Queens: Giddy Up, Katie; Does a Bawdy Good
- Ménage à Moi: The Moose Song; Raise a Toast
- Opal & Jade: ALL MY NUDES; Sorry Not Sorry
- Bedlam Bards: Black Leather Band; Take Out the Trash
- The Cannibal Tudors: Flogging; Z Day In New Market Village
- Ménage à Moi: 50 Shades; 7 Deadly Sins
- Iris & Rose: deformed farm; The Crass Menagerie
- Salty Dick: The Whores of Sailortown; Salty Dick’s Uncensored Sailor Songs
- Pride of Bedlam: Heave Away; Boarding Party