The Bootstrappers on the Sailing Ship Columbia – Disneyland 2019

Sea Shanties on the Rivers of America

The Bootstrappers are a rowdy group of sea-loving pirates who usually roam New Orleans Square at Disneyland, serenading guests with their favorite sea shanties—including the classic “Yo-Ho, Yo-Ho, A Pirate’s Life for Me.” If you’ve ever stumbled upon them outside Pirates of the Caribbean, you know just how entertaining (and hilarious) they can be.

But sometimes, if you’re lucky and the tides are in your favor, you can catch these singing scallywags at sea—aboard the Sailing Ship Columbia, cruising the Rivers of America.

A Pirate Band on a Pirate Ship

Let’s be honest: there’s no better setting for a pirate band than an actual pirate ship. On this summer day in 2019, I managed to catch The Bootstrappers performing on the lower deck of the Columbia, and it was every bit as magical—and mischievous—as you’d hope.

The band had the full attention of every landlubber on board, belting out tunes, cracking jokes, and keeping the high seas lively. It’s a rare moment that adds a whole new layer of charm to an already classic Disneyland attraction.

Join me as we head below deck to experience The Bootstrappers on the Sailing Ship Columbia during Disneyland Summer 2019 in the full video below.