A review copy of “The Shanty of Boldbeard’s Pride” was provided by the publisher. Find more DMs Guild Reviews on my website and YouTube channel.

Support my work by using affiliate links for shopping and pledging via Patreon.

Designed by: Jimmy Meritt

What do we want in a pirate adventure? A rowdy crew? A mutiny? Ship battles? Hidden treasure? Lots of fun references to other popular pirate stories? You’ll find all that in The Shanty of Boldbeard’s Pride, a level 5 mini-adventure that squeezes every salty drop out of its pirate theme.

The adventure is designed for level 5 PCs who ideally already have a ship at their disposal, or at least a way to access the Darklake of the Underdark. The layout and artwork are excellent, with fun character portraits, full-color battle maps, and even the lyrics to the titular shanty, which is also included as a full-on musical number YouTube link and .mp3 file.

The adventure hook of gaining a magical map to the the Boldbeard’s Pride ship takes up the entirety of part one. Unusually the opening hook is an afterthought but here PCs are tasked with winning the map from the singing pirate with a game of Liar’s Dice – with a healthy dose of cheating thanks to some skill checks.

Map in hand they need to take a rowboat into a hidden cave in a cliff, eventually leading down to the Underdark and into the Sunless Sea. There’s meant to be a string of skill checks and random encounters, though all of them are straight combat and could slow down the action too much.

The ship is currently commanded by a Sahuagin Baron named Captain Darkwater, and he has a suitably monstrous crew, including a Mind Flayer quartermaster, ghostly bosun (Boldbeard himself!), and a Kuo-Toa scout. The head of security is a Gelatinous Cube who enjoys wearing hats and spits out weapons for the crew as needed. Love it!

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Hopefully the PCs are willing to play socially here, as a straight-up battle loses much of the fun in the adventure (as well as being pretty damn challenging for level 5 PCs, with a dozen duergar crew mates). The pirates are willing to let the PCs join and prove themselves with a battle against an enemy raiding party.

Once they’re integrated into the crew, it’s time for the PCs to sow the seeds of mutiny. Boldbeard’s ghost will only show them the way to his treasure if they can reclaim his ship. A crew of monstrous misfits is easily turned against one another, with each of the notable officers and crew members having proper desires and motivations. Again, hopefully the players are willing to role-play and have fun with it, rather than relying on skill checks.

The designer smartly includes multiple methods to run the potentially chaotic mutiny with pirate NPCs on both sides, including letting the players temporarily play some of the pirates, or turning the pirates on their side into occasional buffs and other effects. These three different methods take up nearly two pages and seem very well thought-out.

After the last of the pirates are dispatched (sorry pirate allies, y’all gotta go too) and the ship reclaimed, the ghost leads the PCs to Act Three, and we go full-on Goonies with an underground ship cove and a temperamental hill giant named Sloth. Feed him the right mushrooms and you’ve gained a powerful ally, but there are plenty of poisonous mushrooms around to make some big mistakes with.

The dungeon is relatively short and not very combat-heavy, which is the right call coming off the mutiny. I adored the very obvious Pirates of the Caribbean reference with the skeletons and the dog with the keyring, and it all culminates with a big boss battle against a stone golem. Hope you brought a friendly hill giant!

The Shanty of Boldbeard’s Pride does an excellent job incorporating familiar pirate elements and pop culture references, creating a light and enjoyable swashbuckling adventure.


  • Unique setting that combines pirates themes within the Underdark and the Sunless Sea.
  • Excellent balance of combat, exploration, and role-playing.
  • Liar’s Dice is a fun way to make the PCs work for the adventure hook.
  • The monstrous crew is full of fun characters, and there are multiple methods for handling the mutiny.
  • Full color battle maps and fun, cartoonish art throughout.


  • Darklake encounters are limited to simple combat encounters.

The Verdict: The Shanty of Boldbeard’s Pride begins with a game of liar’s dice and ends with a mutiny in the sunless sea and a dungeon excursion that would make the Goonies proud.

A review copy of “The Shanty of Boldbeard’s Pride” was provided by the publisher. Find more DMs Guild Reviews on my website and YouTube channel.

Support my work by using affiliate links for shopping and pledging via Patreon.