Black Sails at Midnight is the second studio album by the Scottish power metal band Alestorm. As with their first album, all the drums tracks were recorded by session drummer Migo Wagner but touring drummer Ian Wilson added additional percussion. The album features string and brass arrangements and folk instruments as opposed to the more heavy metal instrumentation of Captain Morgan's Revenge. The special edition of the album included a live DVD of the band's performance at the 2008 Wacken Festival.
"No Quarter" was previously a demo recording by Battleheart, Alestorm's name before signing with Napalm Records. The signing with Napalm necessitated a name change to avoid confusion with Battlelore. A part of the song contains Alestorm's rendition of the Pirates of the Caribbean theme. "Wolves of the Sea" and "Leviathan" are re-recorded tracks which previously appeared on the LeviathanEP. "P is for Pirate" is a comedy a capella track based on the Sesame Street song C Is For Cookie that is only available on the iTunes version of the album. It features the band singing about how much they love being pirates and their belief that pirates are much better than ninjas.
On March 27, 2009, a split album titled "Black Sails Over Europe" was released on Napalm Records, which features "That Famous Ol' Spiced", "Keelhauled", and "Wolves of the Sea", alongside recordings by Týr and Heidevolk. It was limited to 1000 copies.
On 26 June 2009, a video was released for the song "Keelhauled". Alestorm's first music video. The beginning of the video depicts Christopher Bowes standing up in front of the rest of the crew urging them to allow guitarist Dani Evans to be keelhauled, following a theft. He is promptly keelhauled in a rather realistic manner. As he is keelhauled scenes of the band drinking, gambling and engaging in sexual activity aboard the pirate ship are shown.