ADVENTURE ON THE HIGH SEAS

Publisher: Grim Press

Project Lead: Trevor Armstrong
Designer: J.R. Raffles
Editor: Cody Rakai
Artist: Bob Greyvenstein
Cartography: Sandy Lawson

www.GrimPress.net
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Adventure on the High Seas is a Dungeons and Dragons 5th Edition compatible supplement designed as a resource for game
masters to use in their adventures. This product is compliant with the Open Game License (OGL) located on the last page of this
product.
Product Identity: The following items are hereby identified as Product Identity, as defined in the Open Game License version 1.0a,
Section 1(e), and are not Open Content: All trademarks, registered trademarks, proper names (characters, deities, etc.), dialogue,
plots, storylines, locations, characters, artwork, and trade dress. (Elements that have previously been designated as Open Game
Content or are in the public domain are not included in this declaration.)
Open Content: Except for material designated as Product Identity (see above), the game mechanics of this Grim Press product are
Open Game Content, as defined in the Open Game License version 1.0a Section 1(d). No portion of this work other than the
material designated as Open Game Content may be reproduced in any form without written permission.
Copyright © Grim Press 2022
What's Inside? On the Cover
This release of the Exploring the Realms contains the Bob Greyvenstein depicts an Oath of Plunder Paladin setting
following 5e compatible content: sail in pursuit of fame (or infamy?) while racing for buried
treasure!
MAGIC ITEMS (pg.4). Any sailor worth their salt knows
there’s treasure on the seas more precious than gold and
jewels. These eleven magic items are waiting to be found.
SHIP AUGMENTS (pg.7). Make your ship the terror of the
high seas with these four easy-to-install additions.
ARCHETYPES (pg.8). Four new subclasses that are ready
to plunder untold riches.
BLESSINGS AND BANES: THE BOONS AND CURSES
OF THE SEA (pg.13). The seas are alive with all manner of
blessings and banes. Fifteen new afflictions await those who
travel these waters.
GM VARIANT RULE: GLORY AND INFAMY (pg.16).
Loathed or trusted, feared or famed, a captain’s name is
worth more than his weight in gold. These variant rules allow
GMs to assign their players a reputation on the high seas.
GM VARIANT RULE: FEATS OF FAME AND FORTUNE
(pg.18). Not all skills learned on the high seas can be taught.
These eight feats are earned by only the most infamous.
SAILING THE SEAS: BATTLEMAPS (pg.20). Three
additional battlemaps (with grid and no-grid versions) are
available so your players can loot and plunder to their heart's
content.

In fantasy worlds...
Home to legendary monsters and ruthless pirates,
the high seas are the backdrop to many a
swashbuckling adventure. Where immense
leviathans lurk beneath the waves and cackling
genies fill merchants’ sails with wind, the seas offer
a heady mix of magic and mystery.
 Magic Items - Prizeworthy Plunder
Any sailor worth their salt knows there’s treasure on the seas more precious than gold and jewels. Passed down from pirate to
pirate through bloodshed and larceny, more than a few of these treasures bear cursed legacies.
Bosun’s Backbiter Captain Cawdorn’s Parrotfeather Cap
Weapon (whip), uncommon Wondrous item, legendary (requires attunement)
Rightly feared by upstart sailors, this vicious-looking cat o’ This regal tricorn is adorned with colorful feathers. Your
nine tails serves as both a weapon and a tool of discipline. Charisma score is 19 while you wear this cap, unless it is
You can cast the hellish rebuke spell once (DC 12), and already 19 or higher without it. While wearing the
regain the ability to do so daily at dawn. In addition, an parrotfeather cap, you have advantage on Charisma
incapacitated or restrained creature you damage with the (Intimidation, Performance) checks. The cap’s interior
whip becomes frightened of you for 1 minute, or until it takes functions as a bag of holding.
any damage. You can use an action to pluck a feather from the cap,
which produces an effect depending on its color. The hat has
Cape of Living Kelp one feather of each color in the Parrotfeather Cap Colors
Wondrous item, uncommon (requires attunement) table below. It magically regrows missing feathers on the
night of the full moon.
Crafted by merfolk druids from living seaweed, this cape Roll a d20 whenever a feather is plucked. On a 1, the cap
seems to tangle and writhe with a life of its own. sheds all its remaining feathers, causing their effects to
As a bonus action, you can command the kelp to grow and trigger simultaneously. Whenever the last feather in the cap
detach from the cape, creating either a net or a 50-foot rope is plucked (including when it sheds its feathers), roll a d20.
in your free hand. This creation withers away and disappears On a 1, the cap loses its magic and transforms into a
after 24 hours, or immediately if you use this feature again. gargantuan parrot. This colorful creature, which uses the
When a creature you can see deals damage to you with a statistics of a roc, is hostile to the cap’s wearer and does all in
melee attack, you can use your reaction to tangle them up in its power to carry them off to its lair (the location of which is
the cape. The creature must succeed at a DC 12 Dexterity determined by the GM).
saving throw or be restrained until the end of your next turn.
You can use this reaction once, and regain the ability to do so Parrotfeather Cap Colors
when you roll for initiative. Feather
If the cloak is not immersed in salt water once every 24 Color Effect
hours, it withers away to nothing and disappears. Red The feather magically transforms into a
Scimitar. Attack rolls made with it gain a +2
bonus, and it deals an extra 2d6 fire damage
when it hits. The Scimitar disappears after 24
hours.
Orange The feather disappears in a burst of color,
leaving behind an exotic banquet as if
conjured by the heroes’ feast spell.
Captain Cawdorn’s Yellow You immediately teleport as if by dimension
Parrotfeather Cap door. The feather loses its magic and floats
slowly to the ground in the space you left.
Green The feather magically transforms into a parrot,
which serves you as if conjured by the find
Cape of familiar spell. The parrot uses the statistics for
a hawk.
Living Kelp Blue The feather floats into the sky and disappears.
Unless manipulated by magic, the weather
within 5 miles of you becomes calm, warm,
and cloudless.
Purple You immediately transform as if by the
polymorph spell (you needn’t concentrate).
Any form you assume has a coat consisting of
vibrantly-colored feathers.
White You, any vehicle you’re aboard, and any
creature aboard it, vanish in a puff of feathers
and become invisible. This invisibility ends
after 24 hours, or if any affected creature
Bosun’s attacks, casts a spell, or disembarks.
Backbiter

4
Captain’s Courage Dead Man’s Chest Rarity
Potion, uncommon Type Rarity Effect
Sooner or later, even the fiercest sea captains fall short of Chest of Rare A zombie emerges from an
their legendary reputations. Some drown their sorrows in Dead extradimensional space within the
drink. Others, especially those with access to bootleg Men’s Tales box immediately, and again at
initiative count 20 every round until
alchemists, fill their flasks with a drink of a different kind. the chest is locked. The zombies
When you drink this acrid, wine-like potion, you must attack the chest’s opener. If that
succeed on a DC 12 Constitution saving throw or become creature dies, any remaining
poisoned for 10 minutes. Pass or fail, you are immune to the zombies climb back into the space
frightened condition, gain 3 temporary hit points at the start within the chest and lock it from
of each of your turns, and have advantage on Charisma within.
(Intimidation, Performance) checks for the duration. Devil’s Very The opener must make a DC 20
Locker Rare Constitution save, suffering 10d10
Coat O’ Doubloons piercing damage on a failure or half
Armor (chain shirt), rare (requires attunement) on a success. If this damage reduces
a creature that failed the save to 0
This vest is fashioned from gleaming gold coins strung hit points, its heart is drawn into the
together like chain armor. While wearing the coat, you have chest (typically killing them), and the
chest locks itself.
disadvantage on Dexterity (Stealth) checks. You can perform
a special ritual when finishing a long rest, polishing the Fool’s Very The opener must succeed at a DC
armor and contributing wealth of your own. The ritual Chest Rare 20 Wisdom save or become
consumes up to 500 gold pieces’ worth of coins. For each charmed. While charmed, it does
100gp consumed, the chain shirt’s AC increases by 1 (to a everything in its power to lock the
chest, hide it, and keep its contents
maximum of 18). This increase lasts until you finish a long secret. A remove curse spell or
rest, and ends early if your attunement to the coat is broken. similar magic ends this condition.

Cold Iron Anchor Juke Rare The chest and its contents flash
Box brightly, and the opener can attempt
Wondrous item, rare (requires attunement) a DC 16 Dexterity save to snatch
one object from inside. The chest
This anchor, smithed from cold iron, was torn from the then teleports to its key’s location. A
sunken wreck of a fey-cursed ship. The anchor weighs 50 creature that fails the save is blinded
pounds. By swinging it from an attached chain, you can use it for one hour.
as a melee weapon. The anchor serves as a maul with the Siren Rare The opener hears alluring music, and
reach property. Safe must succeed at a DC 16 Wisdom
When you take the Dodge action while wielding the anchor, save or become charmed. A
you gain temporary hit points equal to your Proficiency charmed creature uses its
modifier and you can’t be knocked prone, moved against your movement to climb into the chest,
will, or magically transported until the start of your next turn. which contains an extradimensional
space large enough to contain it. The
Dead Man’s Chest chest locks itself after a creature
climbs inside, whereupon the
Wondrous item, rarity varies charmed condition ends.
A favorite of paranoid pirate captains, dead man’s chests
range from unassuming lockboxes to ostentatious treasure Coat O’
chests. The chest has immunity to bludgeoning, piercing, and Doubloons
slashing damage, and can survive the crushing pressure of
ocean depths. There is only a single key for a dead man’s
chest. If any other method is used to open a dead man's chest
(such as thieves’ tools, a knock spell, or destructive magic) the
opener suffers a penalty depending on the item’s type, as
shown in the Dead Man’s Chest Rarity table.

Cold Iron
Anchor
Dead Man’s Chest

5
Devil’s Lockpick Staff of Splintered Ships
Wand, rare Staff, very rare (requires attunement by a spellcaster)
This wand, crafted from an iron lockpick, is beloved by Whittled from the drifting remains of a sunken ship, this
pirates who loot first and ask questions later. staff’s crude appearance belies its destructive power. It can
The wand has 6 charges, and regains d3 expended charges be wielded as a Quarterstaff that grants a +2 bonus to attack
daily at dawn. While holding it, you can expend one charge and damage rolls made with it. When you hit a creature with
and use your action to cast the knock spell. When cast this the construct type or a vehicle with the weapon, it takes an
way, the spell’s range doubles, and its deafening blast can be extra 4d6 bludgeoning damage.
heard 600 feet away. An object affected by the spell may also The staff has 20 charges, and regains 2d8 + 4 charges daily
explode, taking 4d10 slashing damage. A creature within 10 at dawn. While holding it, you can use an action and expend
feet of an exploding object must succeed on a DC 15 1 or more of its charges to cast one of the following spells
Dexterity saving throw or take the slashing damage as well. from it, using your spell save DC and spell attack bonus:
arcane hand (5 charges), knock (2 charges), shatter (2
Lash of Mad Laughter charges), telekinesis (5 charges), or thunderwave (1 charge).
Weapon (whip), rare (requires attunement) You can use a bonus action and expend 5 charges to point
the staff at an object or vehicle you can see within 120 feet of
The grip of this whip is wrapped in gnoll hide and dyed a you. The first time the target takes damage before the start of
bright red. When you deal a creature damage with the your next turn, it has vulnerability to that damage.
weapon, you can cast the hideous laughter spell on it as part When the last of the staff’s charges are expended, roll a
of the same attack (DC 15). This property can be used no d20. On a 1, the staff explodes in a shower of splinters,
more than three times, and regains all expended uses daily at destroying it and dealing you 10d10 slashing damage.
dawn. Creatures within 10 feet of you also take this damage unless
If you are charmed or frightened when your turn begins, they succeed on a DC 17 Dexterity saving throw.
you may choose to suffer the effects of hideous laughter until
the start of your next turn (automatically failing saves against
the spell). The charm or fear is suppressed until the laughter
ends.
Message Bottle
Wondrous item, uncommon
This old, empty rum bottle has lost its label and reeks of brine Devil’s
when uncorked. If a message of 25 words or fewer is written
on parchment and placed inside, and the bottle thrown into Lockpick
the sea, a creature of the thrower’s choice they are familiar
with on the same plane of existence telepathically hears the
message. The bottle then sinks and disappears, reappearing
1d10 days later washed up on a random coast with the
parchment bearing the message still inside. Message
Bottle
Lash of Mad Laughter

Staff of
Splintered
Ships

6
 Ship Augments
Make your ship the terror of the high seas with these easy-to-install additions.
Figurehead of Courage Sails of Swift Vengeance
Wondrous item, rare Wondrous item, rare
This inspiring, gold-plated figurehead is cast from iron in the These tattered black sails are usually crusted with old blood,
shape of a snarling lion. It weighs 750 pounds. While but when strung from the mast of a ship or similar vehicle,
installed at the prow of a ship or similar vehicle, the lion’s they catch the wind despite their threadbare state. A creature
mane sways in the wind as if alive. Creatures aboard the aboard the vehicle that assumes the position of captain can
vessel are immune to the Frightened condition, and gain 10 swear vengeance against a creature they are familiar with
temporary hit points daily at dawn. that has wronged them.
Curse. A creature that finishes a long rest on the vehicle All creatures aboard the vehicle gain the benefits of the
must succeed at a DC 13 Wisdom saving throw or develop find the path spell toward this sworn enemy, and the vehicle’s
the flaw ‘I act as though my ship and I are completely speed is doubled along that route.
invincible’. Finishing a long rest on land removes this flaw, as Curse. The captain of a vehicle with these sales attached
does a remove curse spell. gains the flaw ‘I will stop at nothing to get my revenge’ after it
completes a long rest aboard the vehicle. Should the target of
Figurehead of Fear their revenge die, a new target will be selected by the captain
Wondrous item, very rare after it has completed its next long rest. This
flaw can be removed by any effect that
This fearsome ship’s figurehead is cast from bronze in the removes a curse, such as a greater restoration
shape of a charging ram. It weighs 750 pounds. When or remove curse spell.
installed at the prow of a ship or similar vehicle, the ram’s
eyes burn with unquenchable, heatless flames. A creature
aboard the vehicle can attune to the figurehead.
The figurehead has 6 charges, and regains 1d6 charges
daily at dusk. While aboard, you can use an action to cast the
following spells, expending the figurehead’s charges as
appropriate: darkness (1 charge), fear (2 charges),
Figurehead
phantasmal killer (3 charges). of Courage
Alternatively, you can use an action and expend 4 charges
to surround the vehicle with a menacing aura for 1 minute.
The first time any creature that isn’t aboard moves within
120 feet of the vehicle or starts its turn there, it must succeed
at a DC 15 Wisdom saving throw or become frightened for 1
minute.
Figurehead of the Four Winds
Wondrous item, rare
This elegant ship’s figurehead is carved from wood in the
shape of a cackling djinn. It weighs 250 pounds. When
installed at the prow of a ship or similar vehicle, unnatural Figurehead of
winds whip up and surround the vessel. A creature aboard
the vehicle can attune to the figurehead. the Four Winds
The figurehead has 6 charges, and regains 1d6 charges
daily at dawn. While aboard, you can use an action to cast the
following spells, expending the figurehead’s charges as
appropriate: gust of wind (1 charge), wall of wind (2 charges),
call lightning (3 charges).
Alternatively, you can use an action and expend 4 charges
to the control weather spell. When cast in this way, the spell
affects only the intensity and direction of the wind.
Sails of Swift
Vengeance
Figurehead
of Fear

7
 Archetypes
Characters of all stripes can be found on the high seas, from swashbuckling rogues to wandering warlocks. Few archetypes would
be out of place in such a setting, for the seas are a place where travelers from all lands meet. Most share a penchant for freedom
and adventure, not a far cry from the heroes of other genres.
Seafarer
Cleric: Beginning at 6th level, you ignore all difficult terrain caused
Travel Domain by water, and you gain a swimming speed equal to your
The gods of travel are patrons of merchants, explorers, and walking speed.
vagabonds in equal measure. Any who brave the roads, the
seas, or the planes might pay them homage, praying for swift Divine Alacrity
journeys and safe returns. They teach that, with canny At 8th level, you gain the ability to infuse your weapon strikes
preparation and relentless toil, there is no journey too with divine momentum. Once on each of your turns when you
perilous or destination too far. Clerics of these deities view hit a creature with a weapon attack, you can cause the attack
life itself as a journey, reveling in each glimpse of a new to deal an extra 1d8 damage of the weapon’s damage type.
horizon. They speed others on their way, offering comfort to Additionally, you don’t provoke opportunity attacks from that
the weary and guidance to the lost, seeing their fellow party creature for the rest of the turn.
members as traveling companions undertaking the most When you reach 14th level, the extra damage is increased
momentous journey of all. to 2d8.
Travel Domain Spells Messenger of the Gods
Cleric Level Spells Starting at 17th level, when you use your action to attack with
1st comprehend languages, expeditious retreat a melee weapon, you can give yourself advantage on the
3rd find steed, knock attack roll if you move at least 10 feet in a straight line
immediately before making it. If the attack hits, it deals 1d4
5th haste, tiny hut extra damage of the weapon’s damage type for every 10 foot
7th faithful hound, freedom of movement increment you move. After dealing this extra damage, you
9th passwall, teleportation circle
can’t use this feature again until
you finish a short rest.
Blessings of Travel
When you choose this domain at 1st level, you gain
proficiency in the Survival skill. Additionally, you become
proficient with your choice of two of the following tools:
Cartographer’s Tools, Land Vehicles, Navigator’s Tools, or
Water Vehicles. Your proficiency bonus is doubled for any
ability check you make that uses either of those tools.
Gift of the Wanderer
Starting when you choose this domain at 1st level, you can
use your action to touch a willing creature (which can be
yourself) to increase its speed by 10 feet and give it
advantage on ability checks and saving throws against being
grappled or restrained. This blessing lasts 1 hour or until you
use this feature again.
Channel Divinity: Boon of Celerity
Starting at 2nd level, you can use your Channel Divinity to
speed others on their way. As a bonus action, you present
your holy symbol, and each creature of your choice that can
see or hear you within 30 feet of you can immediately use its
reaction to move up to its speed. This movement doesn’t
provoke opportunity attacks and isn’t slowed by difficult
terrain. Creatures that are grappled or restrained may
instead use their reaction to end all such conditions (no roll
required).

8
Druid: Ocean’s Majesty
At 10th level, you hone your mastery of aquatic wild shapes.
Circle of Tides When using your Wild Shape feature to adopt a beast form
The Circle of Tides allows druids to draw on the vast, with a natural Swimming speed, you can transform into a
untameable power of the sea. Composed of both mystics and beast with a challenge rating as high as your druid level
voyagers, druids of this circle are defined and united by their divided by 3, rounded down.
love of freedom, believing the oceans to be beyond mortal Also at 10th level, while fully immersed in water, you can
dominion. Far from attempting to master the waves, the speak telepathically to creatures within 30 feet of you that are
power of these spellcasters waxes and wanes with the ebb also fully immersed in water. The creatures must be beasts,
and flow of the tide. In battle, they allow these forces to or understand at least one language (it needn’t be a language
dictate their magic: gathering slowly like a rolling wave that you speak).
before crashing down with the wrath of a natural disaster.
Land-dwelling druids of this circle are wanderers and Riptide
sometimes outlaws, resisting the efforts of those who would At 10th level, your conjured currents become more powerful.
police the waves. Sea-dwelling druids of this circle are While you have 1 or more Rising Tide levels, you gain a
outcasts and freedom fighters, counting elves, giants, and Flying speed equal to your Swimming speed, can hover, and
merfolk among their number. They rail against the leaders of have advantage on Strength ability checks and saving throws.
undersea civilizations, decrying the arrogance of tyrants who
believe themselves mightier than the oceans they rule. Tsunami
Rising Tide By 14th level, your conjured tides crash with the force of a
natural disaster. While you have 3 levels of Rising Tide, you
Starting at 2nd level, you learn to direct magical currents that can use your action to end the effect early, expending your
surround and empower you. As a bonus action, you can gathered power as a crushing wave.
expend one use of your Wild Shape feature to conjure this You conjure up a magical tidal wave that crashes down on
spectral tide for 1 minute, rather than assuming a beast form. an area within 120 feet of you that you can see. The wave is
When you use this feature, you gain one level of rising tide. 60 feet long, up to 30 feet wide, and up to 30 feet tall. Each
While the effect persists, you can use your bonus action on creature in that area must make a Dexterity saving throw. On
subsequent turns to gain more levels, to a maximum of 3. You a failed save, a creature takes a number of d6 bludgeoning
gain the benefits of your current rising tide level, as well as all damage equal to your druid level, is knocked prone, and is
lower levels. This effect ends and all rising tide levels are lost pushed to the part of the wave that is furthest from you. On a
when the minute ends, or when you cast a spell of 1st level or successful save, a creature takes half as much damage, isn’t
higher. If that spell rolls dice to restore hit points or deal knocked prone, and isn’t pushed. Objects and structures in
damage, you can increase one such roll by a number of d6 the area are also affected: on a failed save, they take twice as
equal to your rising tide level. much damage, but suffer no other effects.
Once you use this feature, you can’t use it
Rising Tide Level Effect again until you finish a long rest.
1 (Low) Your speed increases by 10 feet
and your movement doesn’t
provoke attacks of opportunity.
2 (Moderate) You can add your Wisdom modifier
to the damage rolls of your
weapon attacks and druid cantrips.
3 (High) When you damage a creature with
a cantrip or weapon attack for the
first time on a turn, you can push it
up to 30 feet away from you.

Call to the Sea

At 6th level, your affinity for the ocean deepens. You can hold
your breath for a number of hours equal to your proficiency
bonus, and gain a Swimming speed equal to your walking
speed. If you already have a swimming speed, it increases by
10 feet. These benefits extend to any form you assume using
your Wild Shape feature.
Additionally, whenever your druid spells or class features
move a creature against its will, you can use your reaction to
deal it cold damage equal to your proficiency bonus.

9
Paladin: Channel Divinity
When you take this oath at 3rd level, you gain the following
Oath of Plunder two Channel Divinity options.
All That Glitters. You can use your Channel Divinity to
The Oath of Plunder calls to paladins seeking riches and bring out the worst in people, clouding their judgment with
renown. Far more than mere mercenaries, these warriors greed. As an action, you can present an object worth at least
wear their greed like armor, heedless of life and limb in their 10gp and force a creature within 30 feet of you who can see it
quest for spoils, tempering their mercy in favor of might. to make a Wisdom saving throw. The creature has
Most adorn themselves with gems and trinkets, favoring disadvantage on the saving throw if the object is worth at
glittering gold over practical steel. The purity of their least 10gp for each of its hit dice. On a failed save, the
selfishness is like a rallying cry, lighting a fire under the very creature is charmed by you for 1 minute. The effect ends
worst of scoundrels. Many are bandit lords or pirate captains, early if you or your companions harm the target.
as the seediest of lowlifes seem to flock to them. At their best, Plunderer’s Mark. As a bonus action, you can utter a vow
they are dashing daredevils humbling the rich. At their worst, of covetousness for an object you can see within 60 feet of
these knight-pirates are pitiless tyrants, uncaring of the you, using your Channel Divinity. Your movement increases
destruction their pillaging leaves in its wake. Only a fool by 10 feet, and you gain advantage on attack rolls against any
stands between such a paladin and their prize. creature wearing or carrying the object. This effect lasts for 1
minute, or until you use an action to dismiss it. While the
Tenets of Plunder effect persists, you can’t move away from the object
Paladins who take this oath display the tenets of plunder as a voluntarily.
warning to all: stamped on their glittering regalia or tattooed
on their flesh. Armored by Greed
No Thirst Unquenched. Desire is the beacon that guides Starting at 7th level, you cast off steel in favor of glittering
you. Never judge yourself, or others, for their ambitions. gold. While adorned with jewelry, wearing no armor, and not
Humble the Proud. Wealth and prestige belong to those wearing a shield, your base AC equals 16 + your Charisma
powerful and driven enough to claim them, not to nobles and modifier.
charlatans living off the toil of others.
Give Nothing Back. Your spoils are yours by conquest to
do with as you please. Don’t waste your pity on those who Soul of Avarice
refuse to fight. Starting at 15th level, your desire begins to border on
insanity. While you can see the object of your Plunderer’s
Oath Spells Mark, your speed increases by a further 10 feet (for a total of
You gain oath spells at the paladin levels listed. +20 feet) and you have disadvantage on saving throws against
being Charmed. For the same duration, both your attacks and
attack rolls made against you score a critical hit on a roll of
Oath of Plunder Spells 18, 19, or 20.
Paladin Level Spells
3rd command, identify Larger than Life
5th heat metal, locate object At 20th level, folklore immortalizes you as a marauder of
9th bestow curse, fear legend. Your reputation is a cautionary tale to merchants and
monarchs, and a rallying cry to all who would plunder in your
13th freedom of movement, secret chest wake. As an action, you can magically adopt your
17th dominate person, mislead exaggerated, legendary persona, gaining the following
benefits for 1 minute:
You have advantage on all saving throws.
The first time any enemy creature moves within 30 feet of
you or starts its turn there during a battle, the creature
must succeed at a Wisdom saving throw (DC 8 + your
proficiency bonus + your Charisma modifier) or become
frightened of you for 1 minute.
Your size increases by one category, you gain advantage
on ability checks that use Strength, and the damage of
your melee weapons increases by 1d8.
Once you use this feature, you can’t use it again until you
finish a long rest.

10
Wizard: Ship in a Bottle
At 10th level, you learn new and unusual ways to safeguard
Ship’s Mage ships. You can perform a special 10-minute ritual while
touching an unoccupied vehicle, concentrating as if on a spell.
Wizards of this tradition verse themselves in rites and rituals When the ritual concludes, the vehicle becomes a tiny
of safe passage, forgoing their libraries in favor of sailors’ magical object. You can have only one such object at a time,
bunks. They relish the opportunity to travel, hunting for and when you finish the ritual, any previously shrunken
arcane lore from distant lands. At a bustling port, such a vehicles return to normal (see below).
wizard could name their price, pledging their services to the A creature holding the object can use an action to place it
highest bidder. It’s a rare sailor that recognises the value of a on the ground or into water and speak a command word
spell scroll, and most crews will barter such treasures for a chosen by you. The vehicle then rapidly grows until it reaches
wizard’s protection. its original size. Each creature in the area where the vehicle
appears must make a Dexterity saving throw against your
Priceless Practicality spell save DC, taking 3d10 bludgeoning damage on a failure,
When you select this tradition at 2nd level, you learn two or half as much on a success. In either case, the creature is
languages of your choice. You also become proficient with pushed to the nearest unoccupied space adjacent to the
Land and Water Vehicles, and learn the druidcraft and vehicle.
mending cantrips. If there’s insufficient space for the vehicle to grow, it grows
as much as it can and is then destroyed (reducing it to 0 hit
Rites of Sea and Sky points). The vehicle’s wreckage is difficult terrain.
Starting at 2nd level, you can perform a magical rite to Part of the Crew
protect your traveling companions. While holding a staff, you
can use a bonus action to begin the rite, which lasts until the By 14th level, you’ve honed not only your spells but also your
end of your next turn. For the same duration you, and allies camaraderie. When you cast a Wizard spell of 5th level or
within 10 feet of you, gain a +1 bonus to AC and saving lower that targets only one creature and doesn’t have a range
throws and can't be moved or knocked prone against your of self, you may alter the spell to target a number of
will. If you’re aboard a vehicle, it gains a bonus to its AC and additional, willing creatures up to your Proficiency bonus.
saving throws equal to your Proficiency modifier. Once you use this feature, you can’t use it again until you
You can use a bonus action on subsequent turns to extend finish a long rest.
the rite, which continues until the end of your next turn. The
rite ends early if you move, or if you choose to dismiss it (no
action required).
After starting the rite, you can’t do so again until you finish
a long rest.
Explore the Arcane
By 6th level, you’ve plundered knowledge from across the
world. Choose two different options from the list below:
Choose a spell from the Bard, Sorcerer, Warlock, or
Wizard class list. The spell must be of a level you can cast,
as shown on the Wizard table, or a cantrip. The chosen
spell is added to your spellbook, and counts as a Wizard
spell for you.
Choose one skill in which you have proficiency. You gain
expertise with that skill, which means your proficiency
bonus is doubled for any ability check you make with it.
The skill you choose must be one that isn’t already
benefiting from a feature, such as Expertise, that
doubles your proficiency bonus.
You gain proficiency with one skill of your choice
and one of the following: a tool, a martial weapon,
or a language.
At 10th level, you may choose one more option from the
list, which may be an option you’ve already chosen.

12
 Blessings and Banes:
The Boons and Curses of the Sea
The seas are rife with sailors’ superstitions. Tall tales abound of cursed crews and merfolk magic. As often as not, even the most
blusterous rumors hide a kernel of truth. The seas are alive with all manner of blessings and banes.
The following is an arsenal of supernatural effects, each of Breath of the Mer (Boon)
which is either a curse or a boon. Boons are magical
blessings that empower the recipient, while curses are Appearance: Faint scar-like lines appear at the base of your
detrimental and can be deadly. Unless stated otherwise in its neck. While immersed in water, your skin has a silvery
description, the effects of a curse or boon are permanent. At shimmer that looks like scales.
the GM’s discretion, a remove curse spell or similar magic The peoples of land and water might live apart, but
can end a curse, but neither boons nor curses can be powerful magic is able to bring them together. Most such
dispelled. An effect’s description specifies if it’s a boon or a fables are cautionary tales, of course, that speak of sailors
curse. lured into the sea, never to return.
You can breathe both air and water, and have a swimming
Boons of the Sea speed equal to your walking speed, or a walking speed equal
Boons provide an alternative to treasure and magic items. to your swimming speed if you do not have one. While
The GM might award a character a boon for… immersed in water, your speech can be heard and understood
by any creature within 30 feet of you, provided that that
Earning the favor of a powerful ocean being, such as a creature understands at least one language.
merfolk monarch, water genie, or sea god.
Solving a puzzle or mystery in a place of ancient or Blistering Barnacles (Curse)
magical significance. Appearance: Ocean molluscs, such as limpets and barnacles,
Striking the killing blow against a villain whose plans
posed a threat to the high seas or their denizens. cling to your skin like boils.
Your movement speed is reduced by 10 feet, and you have
Alternatively, the GM might use a Boon to empower a disadvantage on Dexterity ability checks. You can pry off the
monster, making for a more interesting or challenging barnacles when you finish a short or long rest, suffering 4d4
encounter. Many of these boons can adapt an encounter to be bludgeoning damage.
more fitting for a high seas setting, while few are so powerful
that they could change an encounter’s CR. Bulwark of the Ancients (Boon)
Curses of the Sea Appearance: A crust of ocean coral or porous rock protects
your skin, inlaid with indecipherable golden runes. Many a
Curses provide an alternative to traps and hazards. A mist-shrouded island or ocean floor is the resting place of an
character might suffer a curse for… evil best forgotten. The sea embraces its role as guardian,
Attuning to a cursed magic item. defending those who fight to protect its secrets.
Taking treasure from a place of ancient or magical When you are dealt damage, you can use your reaction to
significance. activate the bulwark, granting you resistance to all damage
Defiling a sea god’s shrine or slaying their servants. until the end of your next turn (including the triggering
Failing a saving throw against a remove curse spell. instance). For the same duration, you are Restrained, and any
nonmagical melee weapon that damages you is destroyed
The GM can easily adapt a magic item to carry a curse. A unless its wielder succeeds at a DC 12 Dexterity saving
character begins to suffer the curse’s effect when they attune throw.
to the item, or (if it doesn’t require attunement) when they You can use this feature once, after which you must finish a
touch it for the first time. short rest before you can use it again.
A curse might be lifted by some special action as the GM
sees fit, such as returning a stolen treasure or restoring a Cursemarked (Curse)
defiled shrine.
Appearance: Tattoo-like markings spread to cover your skin,
depicting ominous runes or the leering faces of fiends.
A Cursemarked sailor is a locus for bad luck. Some crews
deliberately travel with such an unfortunate person, using
them as a lightning rod for baleful magic.
You fail all saving throws against curses automatically.
Additionally, when you touch a creature that’s suffering a
curse, the curse is transferred to you and that creature is
cured. Curses that can’t be removed with a remove curse
spell are not transferred.

13
Deep Reprieve (Boon) Might of Crashing Waves (Boon)
Appearance: Your skin is pallid and slightly translucent, and Few forces compare to the crushing wrath of the tide, which
your pupils grow to encompass the whites of your eyes. wears even the mightiest rock down to sand eventually.
Few who witness the ocean’s otherworldly depths return, Those who can harness such power are fearsome indeed.
and those that do are never the same again. When you hit a creature with a melee attack, you may
You can breathe water, have resistance to cold and choose either Whelming Wave or Relentless Tide. The
bludgeoning damage, and can comfortably survive in attack’s target suffers an additional effect depending on your
environments of extreme pressure, such as ocean trenches. choice:
You can cast dancing lights, requiring no components, and
have blindsight within 30 feet of you. Whelming Wave: Unless it is huge or larger, the target is
pushed 10 feet away from you. If this brings it into contact
Drowned (Curse) with an impassable fixture, such as a wall, for the first
time on a turn, it takes bludgeoning damage equal to your
Appearance: Your skin is pale and clammy, and reeks of Proficiency modifier.
brine. Your body is bloated, as if drowned in saltwater. Relentless Tide: The next time the target makes a saving
It is said that the spirits of vengeful sailors inflict this throw before the end of your next turn, it rolls a d4 and
curse, sharing their fate with those that failed to save them. subtracts the number rolled from the result.
You have vulnerability to Cold and Piercing damage, and
your dreams are haunted by a sailor’s dying memories. When Myth and Mystery (Boon)
you would remove a level of exhaustion at the end of a long The high seas enjoy a rich mythology, the home of fantastical
rest, you must first succeed at a DC 13 Wisdom save. On a heroes and legendary monsters. There is wisdom in every
failure, the level of exhaustion is not removed (you gain other sailor’s superstition, and only those steeped such legends can
benefits of the rest as normal). hope to join them.
You gain a +10 bonus on Intelligence (history) checks, and
Groggled (Curse) have advantage on Charisma ability checks to start or spread
Appearance: Your nose and cheeks turn red, and you slur rumors. When you hear a rumor spoken aloud, you
your words unless speaking in short sentences. automatically learn if the speaker believes the tale, unless
Whether or not you’ve touched a bottle, you are constantly, they are shielded from divination magic.
debilitatingly inebriated. Additionally, you can cast legend lore once, requiring no
You have disadvantage on ability checks using Dexterity or components, and regain the ability to do so after 7 days.
Charisma, and on saving throws against becoming poisoned.
As an action, you can spend a hit dice to focus and sober up. Ocean’s Harmony (Boon)
Rather than gaining hit points, you suppress the penalties of Appearance: Those who look into your eyes see a silvery
this curse for the next ten minutes. shimmer, as if staring into calm water by the light of the
moon.
Living Death (Curse) The seas are a place of strange wiles and alluring songs, a
Appearance: Your flesh wastes away, leaving only a living wellspring of power for any who can resist their
skeleton. You can’t recall the taste of food or drink, the smell enchantments.
of salt nor the feel of the sea breeze. You have proficiency in the performance skill, and
This dreaded curse punishes the looters of ancient graves, advantage on saving throws against being Charmed. You can
stripping them of the ability to feel. Deprived of all mortal cast the sanctuary spell up to three times, and regain all
pleasures, the victim’s wealth and glory become meaningless, expended uses daily at dawn.
leaving only their greed for greed’s own sake.
You’re no longer required to eat, drink, or breathe, and can’t Ocean’s Vitality (Boon)
gain any benefit, such as that of a potion, that requires you to Appearance: Swarms of fey spirits, appearing as crustaceans
do so. Magical healing you receive restores half as many hit or flying fish, surround you. Patches of coral grow on your
points. Additionally, you gain resistance to poison damage. clothes or skin.
Deprived of all sensation, whenever you finish a long rest, Though a sailor might live out their life in ignorance, the
you must succeed at a DC 10 Charisma saving throw or ocean beneath them thrives with boundless life. Every reef
become demoralized, represented by a level of exhaustion. If and wreck is a microcosm.
you fail three such saving throws consecutively, your As an action, you can spend one hit dice to restore your hit
alignment changes to Neutral Evil, and you either fall asleep points. The hit points you regain are equal to one roll of the
forever or become an NPC under the GM’s control. die plus your Constitution modifier. If this leaves you with
fewer than half of your maximum hit points, you immediately
regain as many hit points again.
Additionally, you can cast the animal messenger spell at
will, requiring no components.

14
Sirensong (Curse) The Black Spot (Curse)
You can’t stop humming a particularly catchy tune. Creatures Appearance: An ink-black blotch appears on your skin,
within 30 feet of you have disadvantage on perception checks typically on the palm of your dominant hand. According to
that rely on hearing and, unless deafened, creatures legend, a sailor that bears the black spot has been marked for
automatically succeed at perception checks to hear you. As death, doomed to draw the attention of ocean horrors. Most
an action, you can suppress these penalties, not singing the crews wouldn’t hesitate to throw you overboard, fearing the
tune again until your concentration is broken (as if creatures that follow in the curse’s wake.
concentrating on a spell). Large or larger creatures have advantage on melee attack
A creature that finishes a short or long rest within earshot rolls against you unless there are no other targets within
of you must succeed at a DC 10 Wisdom saving throw or else their reach.
suffer this curse. If your adventure uses the rules for random encounters,
the GM rolls twice to determine if encounters occur (applying
the most perilous result).
Unquenchable Thirst (Curse)
Appearance: Your skin becomes flaky and dry, and your lips
are always cracked as if parched with thirst.
No matter how much you drink, you cannot slake your
thirst. When you finish a long rest, you must succeed at a DC
12 constitution saving throw or gain a level of exhaustion.

15
 GM Variant Rule: Glory and Infamy -
Reputation on the High Seas
In worlds of seedy pirates where ends justify means, to whom do the wealthy entrust their precious cargo? When a merchant spots
sails emblazoned with a pirate’s mark, what drives their decision to fight, to flee, or to fold? With only a ship and a crew to see
them safe, an adventurer’s wealth and experience pale in comparison to the value of their reputation. Loathed or trusted, feared or
famed, a captain’s name is worth more than his weight in gold.
Using this optional rule, GMs can award reputation alongside Benefits of Reputation
wealth, experience, and loot. A party’s reputation represents
their fame (or infamy) in their campaign’s setting. Where appropriate, the GM might allow a character to
Implemented properly, reputation rewards adventurers for substitute their party’s reputation for their modifier on
their larger-than-life deeds, encouraging parties with a flair Charisma (intimidation) and Charisma (persuasion) checks.
for the dramatic. Reputation can also police a party in a For example, a pirate demanding that a merchant surrender
setting without conventional authorities: nobody respects a their ship might use their Reputation of +7 in place of their
pirate who preys on the helpless, or trusts a courier who Charisma (intimidation) modifier to avoid a fight. When
absconds with their valuable goods. hiring sailors, a character might substitute their crew’s
Of course, as for any swashbuckling story, a crew’s reputation for their Charisma (Persuasion) when promising
reputation is often exaggerated, promoted through bluster or payment in gold they don’t yet have.
carefully placed bribes. Conversely, a savvy rival might At the GM’s discretion, characters might gain additional
undermine a party’s reputation by spreading scandalous benefits as their party’s reputation increases. The feats
rumors. How Reputation Works Setting sail for the first time, presented in Feats of Fame and Fortune have Reputation
a party’s reputation score is usually 1. Though an insightful prerequisites, and the table below contains suggestions for
benefactor might spot their potential, few hirelings will trust passive advantages.
that they are good for the coin, and few quest-givers of note
will take a chance on them. By earning and maintaining a Reputation Score Benefits
reputation, this score can be increased as high as 20. Reputation
Reputation, like experience or inspiration, is awarded to the Score Effect
party at the GM’s discretion, but certain actions and 1-3 None. The party are unlikely to be entrusted with
achievements (outlined later) can increase or reduce it. important tasks, and probably hold low ranks
Unless the GM decides otherwise, a party’s reputation can on ships run by NPC captains.
never exceed their average class level by more than 2.
The GM might limit the following factors using the party’s 4-6 The party can always find a place to rest, hide,
or recuperate among commoners, and can get
reputation score: away with minor criminal offenses such as
Quests: The seas suffer no shortage of daring crews. refusing to pay for food or breaking down
Quest-givers are unlikely to entrust a mission to a party if doors. Whether loved, feared, or respected,
their reputation (rather than their class level) is lower than common folk have heard of the party, and that
the quest’s suggested level. Of course, a blusterous crew with it’s better to help them out than to risk
an exaggerated reputation might just as easily get in over crossing them.
their heads – offered missions appropriate for characters of a 7-9 If every party member agrees, a character can
higher level. reroll a failed Deception, Intimidation, or
Hirelings: Few self-respecting sailors will entrust their Persuasion check. If the new roll passes, the
lives to a captain they’ve never heard of. When recruiting party’s reputation is reduced by 1. The party is
crewmates or soliciting services such as spellcasting, the widely renowned for their daring deeds. In
maximum CR of available NPCs is limited to half the party’s times of need, they can swear on their
reputation, or call in a favor or two from a
reputation score (rounded down). powerful benefactor.
10-16 Each character gains a feat to match their
exaggerated capabilities (the following
chapter, Feats of Fame and Fortune, presents
additional options). Ridiculous nicknames and
preposterous rumors abound, surrounding the
party in myth and mystery.
17-20 Each Character gains a Boon of the Sea (these
boons are detailed in a later chapter, Blessings
and Banes). The party’s legend is known
across the planes, and the gods themselves
make wagers on their careers.

16
 Gaining and Losing Reputation
The GM is encouraged to award reputation for completing
quests, reaching adventure milestones, and performing
daring deeds. The achievements below provide examples of
actions that could increase or reduce a party’s reputation.
Award Reputation for…
Slaying Sea-Monsters Defeating creatures whose
challenge ratings exceed the party’s reputation score.
Besting Rivals Defeating a crew or captain whose
reputation exceeds the party’s in battle, or in a contest
such as a ship race or drinking game.
Saving the Day. Defending a famous merchant’s fleet
from pirates or an island outpost from marauding
monsters; any deed that puts powerful people in the
party’s debt.
Surviving Certain Death. Recovering from a mutiny,
marooning, natural disaster, or kraken attack can do
wonders for a crew’s reputation.
Spreading Rumors. Not all good reputations are
deserved. A crew that spends downtime and wealth
placing bribes and telling tall tales might be able to trade
their money and time for reputation.
Reduce Reputation for…
Fleeing from Battle. Although it’s always better to live to
fight another day, word travels quickly when a crew backs
down from a challenge.
Defeat by a Rival. As a crew’s reputation grows, they’re
sure to draw the attention of upstarts looking to prove
themselves. Being defeated in battle by a rival crew with a
lower reputation score, or in a contest such as a ship race
or drinking game, can damage the party’s reputation, as
could refusing such a challenge.
Preying on the Weak. There may be no honor amongst
thieves, but a pirate who preys on the helpless is quickly
accused of avoiding a real fight.
Absconding with Chartered Goods. Losing (or stealing)
an employer’s cargo, taking payment for a job they failed
to complete, or otherwise reneging on the terms of a
contract or agreement harms the party’s reputation.
Malicious Rumors. Rivals and malefactors can spend
time and money spreading hurtful rumors. A crew that
spends time in a port, tavern, or courtroom is likely to
hear these tales being told.

17
 GM Variant Rule: Feats of Fame and Fortune
Not all skills learned on the high seas can be taught. Many an old salt attributes their success to a sailor’s knack: an uncanny
ability honed by a life on the waves. An adventurer with a voyage or two under their belt might learn a handful of these talents for
themselves.
Using this supplement, new feats are available to characters Devilish Charm
alongside options from other sources. If your campaign
doesn’t use the optional Reputation mechanic outlined in the Prerequisite: Reputation 6 or higher
previous chapter Glory and Infamy, disregard a feat’s
reputation score prerequisite You have a quick wit and a disarming smile, and are not
above turning either on your foes. You have 3 devilish charm
Arsonist points, one of which can be used on any of the following
abilities:
As a pyromaniac with a knack for starting fires, you’re
happiest when watching a ship go down in flames. Your skin When a creature you can see hits you with an attack, you
is a patchwork of burns and scars, testament to your can use your reaction to add your Charisma modifier to
disregard for danger. You gain the following benefits: your AC for that attack, potentially causing the attack to
miss you.
You are proficient with oil, and with improvised weapons Before rolling an Intelligence, Wisdom, or Charisma
that deal fire damage, such as torches. You can add your saving throw, you can use your reaction to add your
proficiency bonus to the fire damage you deal with Charisma modifier to the result.
improvised weapons. When you would make a Charisma ability check at
When you deal fire damage to a creature using an disadvantage, you may instead make the roll at advantage.
improvised weapon, you can set it ablaze. The creature
takes d4 fire damage at the start of each of its turns until You regain your expended devilish charm points when you
it, or a creature within reach, uses an action to douse the finish a long rest.
flames. After setting a creature ablaze with this feature,
you must finish a short rest before you can use it again. Drunkard’s Luck
Fire damage you deal to objects and structures from any Thanks to a heady mix of plundered and bootleg grog, you
source is doubled. are rarely sober. While you can handle your drink better than
Braggart most, you’re no stranger to a drunken brawl, and have learned
to turn your tipsy staggering to your advantage. You gain the
Prerequisite: Reputation 3 or higher following benefits:
You have a fool’s confidence and a boastful tongue. On your When knocked prone against your will, you can use your
first turn in combat, you can make a boast as a bonus action. reaction to roll up to half your speed in a direction of your
When you make the boast, you gain temporary hit points choice without provoking attacks of opportunity.
equal to either your level or your party’s reputation score While poisoned, your attack rolls do not suffer
(whichever is greater). While you have these hit points, you disadvantage, you can roll d8 + your Strength modifier for
are immune to the frightened condition. Any remaining the damage of your unarmed strikes, and you have
temporary hit points are lost when the combat ends. If all the advantage, rather than disadvantage, on ability checks to
hit points are lost before then, you become frightened until grapple and shove creatures.
the end of combat.
Hunter
Cutthroat Prerequisite: Reputation 6 or higher
Prerequisite: Reputation 3 or higher You’ve tested your mettle against beasts of sea and sky, and
You have a talent for treachery and no interest in fighting fair. know all manner of cruel tricks to lay them low.
You gain proficiency in either the Sleight of Hand or Stealth When you damage a creature by hitting it with an attack, it
skill (your choice). must succeed at a Constitution saving throw (DC = 8 + twice
Additionally, when you hit a creature that is surprised, or your proficiency bonus) or lose the benefits of its climbing,
that cannot see you, with a melee weapon attack, you can burrowing, and swimming speeds until the end of your next
cause that attack to deal an additional d6 damage of the turn. If the creature is flying and can’t hover, it instead falls
weapon’s type. A creature that takes this damage may not prone if it fails the save.
take reactions until the end of your next turn. After dealing You can use this feature only once each turn. A creature
this extra damage to a creature, you can’t use this feature on that passes its save against this feature becomes immune to
that creature again until you finish a short rest. this effect until you finish a short rest.

18
Ruthless Sea-Legged
Prerequisite: Reputation 9 or higher Prerequisite: Reputation 3 or higher
You have a reputation for mercilessness. Tales abound of the You’ve grown accustomed to life on the sea, surviving storms
blood you’ve shed, and the grisly fates met by those who stood in the crow’s nest and even some ‘trips’ overboard. Your sure-
in your way. footedness turns novice sailors green with envy (or perhaps
When you reduce a hostile creature to 0 hit points, you may just sea-sickness). You gain the following benefits:
gain temporary hit points equal to your proficiency bonus and
make a Charisma (Intimidation) check. Hostile creatures You have advantage on ability checks and saving throws to
within 30 feet of you who can see or hear you must succeed avoid falling prone.
at a Wisdom saving throw against your check result or While not wearing heavy armor, you have a climbing and
become frightened of you for 1 minute. swimming speed equal to your walking speed.
You can use this feature a number of times equal to your The time for which you can hold your breath is doubled.
proficiency bonus, and regain all expended uses when you You gain proficiency in either the Acrobatics or Athletics
finish a long rest. skill (your choice).

19
 Sailing the Seas: Battlemaps
The following maps have been provided as an additional resource. May your players plunder the high seas with reckless abandon!
OPEN GAME LICENSE
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