• John J. O'Hara

Your D&D Party Has to Pilot a Ship. Now What?

In a campaign I ran a few years ago, the PCs cleared out a pirate cove and claimed the pirates’ treasure horde for themselves. The greatest prize of all: the pirates’ cog, a single-mast, two-deck ship small enough to be operated by a crew of 4-6. They also found a map of the coast and some offshore islands and a wand that could create gusts of wind.

There was only one problem: None of the characters knew the first thing about sailing. The ranger could keep them from getting lost, but none of the other members of the party could hoist a sail or cast an anchor or tell a mainmast from a mizzenmast to save their lives (and neither can I, to be honest). Before they could use this ship, they would either have to hire a crew, a great expense for a mid-level party, or get themselves some training.

Your own party will likely find themselves in a similar situation at some point in their adventuring careers. However you come into possession of a ship, it’s important that your characters know how to use it!

The Mechanics of Navigation


The ships listed in the Player’s Handbook move between 2.5 and 4 MPH, which means they will traverse anywhere between 60 and 96 miles in 24 hours. Bad weather or favorable winds can lengthen or shorten a voyage.

Skill checks

Sailing is hard work. It’s also a team effort, and a safe voyage will require successful skill checks in all six abilities.

Securing sails and rigging, climbing masts, hoisting anchors, and even turning the wheel all require some amount of strength, and working long shifts in heavy wind and rain on rough seas requires a fair bit of endurance. Characters with high Strength and Constitution scores are well-suited to the more laborious aspects of ship navigation.

High-dexterity characters also have a part to play. There are lots of knots to tie, and a ship at sea for any length of time will need some repairs. You want a rogue with a strong sense of balance.

Intelligence and Wisdom are probably the most critical abilities when it comes to navigation. In the absence of navigator’s tools, a smart enough PC can figure out how to use a map, star chart, or compass with some accuracy (that is, if they pass a DC 15 Int or Wis check).

Charisma might seem purposeless on the high seas, but someone has to whip your crew into shape! A high-charisma character, such as a paladin, warlock, or bard (if the bard isn’t busy keeping the crew entertained) is a natural fit for this position. A PC in the captain role can win and retain the loyalty of the crew, without whom all the astronomical and nautical knowledge in the world is useless.

Navigator’s Tools

Navigator’s tools include everything a character needs for navigating at sea. It is safe to assume that these tools include maps, star charts, a compass, an astrolabe, and a sextant. Characters with the sailor background gain proficiency in these tools.

The rules do not state which type of ability check is associated with navigator’s tools, but it considering what it takes to use them, Intelligence and Wisdom are probably the abilities most likely to be called upon in the course of navigating a ship.

Who Should Pilot?

Most ancient and medieval sailing ships could be operated by crews as small as ten, so a D&D party who finds themselves in possession of a ship could fill half of the roles themselves. Rather than hire a navigator for 2 GP per day, a member of the party with the right skills could navigate the ship themselves.

A character with the sailor background is a clear choice for navigator since proficiency in navigator’s tools is a must for this role. A knowledge cleric could also fill in in a pinch using their Knowledge of the Ages ability, which affords proficiency in any tool kit for 10 minutes per day. Ten minutes might just be enough time to read a map or use a compass and plot a course.

A ranger’s Natural Explorer ability would also be useful for a different kind of navigation: reading the stars, the sun, the wind, the waves, and even the shapes of clouds, like the ancient Polynesian explorers.

Rather than just a convenient excuse for fast travel, a ship holds vast potential for both mechanical and role-playing fun. Thinking about the possibilities makes me want to develop a campaign in which the PCs are the crew of a ship myself.


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