Travel at Sea
It's not just pirates and sea monsters that make journeys on the sea so treacherous. Foul weather, nautical accidents, infested food, illness, and worse all conspire to send even the most capable crews to watery graves. The following rules help adjudicate travel at sea, specifically voyages of an hour or more. This material builds on the travel rules in the Player's Handbook and the Dungeon Master's Guide.
Pace
Ships travel at a speed given in their stat blocks. Unlike with land travel, ships can't choose to move at a faster pace, though they can choose to go slower.
If a ship's mode of movement takes damage, it might be slowed. For every decrease of 10 feet in speed, reduce the ship's travel pace by 1 mile per hour and 24 miles per day.
Environs
Despite the placid surface, the seas present a number of different geographical phenomena that can make travel... interesting.
Activity While Traveling
The activities available to a ship's crew and passengers are a bit different from the options available to a group traveling by land.
A number of activities are restricted to certain officers, unless the DM rules otherwise. For example, a DM might allow a bard to engage in the Raise Morale activity by playing bawdy songs on deck to lift the crew's spirits.
The party's pace has no effect on the activities they can engage in while traveling by ship.
Draw a Map
A ship's captain often undertakes this activity, producing a map of the ship's progress and helps the crew get back on course if they get lost. No ability check is required.
Forage
The character casts fishing lines, keeping an eye out for sources of food, making a Wisdom (Survival) check when the DM calls for it.
Raise Morale (First Mate Only)
The first mate can manage the crew's time to grant extended breaks, provide instruction, and generally improve the quality of life on the ship. Once every 24 hours, if the crew's quality score is 3 or lower, the first mate can make a DC 15 Charisma (Persuasion) check. On a successful check, the crew's quality score increases by 1.
Navigate (Quartermaster Only)
The quartermaster can try to prevent the ship from becoming lost, making a Wisdom (Survival) check when the DM calls for it. (See "Becoming Lost" in chapter 5 of the Dungeon Master's Guide for more information.)
Noticing Threats
Use the passive Wisdom (Perception) score of the player characters or the crew to determine whether anyone on the ship notices a hidden threat. The crew has a passive Wisdom (Perception) score equal to 10 + the crew's quality score. The DM might decide that a threat can be noticed only by characters in a specific area of the ship. For example, only characters below deck might have a chance to hear or spot a creature hiding on board.
Repair (Bosun Only)
At the end of the day, the ship's bosun can make a Strength check using carpenter's tools. On a 15 or higher, each damaged component regains hit points equal to 1d6 + the crew's quality score (minimum of 1 hit point). A component other than the hull that had 0 hit points becomes functional again.
Stealth (Captain Only)
The ship's captain can engage in this activity only if the weather conditions restrict visibility, such as in heavy fog. The ship makes a Dexterity check with a bonus equal to the crew's quality score to determine if it can hide.
Hazards
Ships face a number of Hazards that can threaten the life (and/or cargo!) on board a vessel.