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  • Writer's pictureMark S. Cookman

Alternate Sailor Backgrounds for D&D 5e: The Explorer / Deep Water Sailor

For my own D&D 5e campaign, which is based mostly upon the high seas of various worlds, one background for a generic sailor just didn't work. On the coast, everyone sails. Because there are many different types of sailors and nautical personalities, I felt that there needed to be more variety than just one generic sailor so I created five additional nautical backgrounds to supplement the original sailor/pirate. They are merchant sailor/smuggler, marine, deep water sailor/explorer, jack tar, and fisherman/whaler. It is my plan to release one each day of this week. This is the third one. Here is where you can find the entire list, in case you missed them. Finally, I hope you enjoy the explorer / deep water sailor.

Explorer / Deep Water Sailor

You were born on a ship in the middle of the sea and you will probably die on one as well; you can't imagine any other life. You were brought up around hard-working men and women of the sea. Since you were a child you have dreamed about sailing around the whole world. You have worked hard towards this goal, sailing longer and farther as a young teen than many in your home village had ever gone. You have seen numerous wonders and experienced many strange events in your travels. You've met many people from many different and unique cultures during your numerous voyages. You've seen creatures that defy description and beheld the wealth of a thousand kings, even so your wanderlust still remains unsatisfied. Whether you sail around the globe to find new worlds to colonize, new worshippers to convert, or new treasures to confiscate, you care more about sailing towards a fresh discovery than any of those things in your heart of hearts.

You have spent more of your life with the deep blue surging just below the decks, than you have on land. You've seen amazing spectacles of nature that words would fail to describe and met intriging sea-dwelling species with laws and morals of their own. You are thought of by other sailors as a "true salt", someone who knows well the rigors of sailing and life at sea. You can trade stories for drinks in nearly any sea-side tavern or inn. People look up to you. Even those who do not like you respect your abilities and knowledge.

After choosing this background, you must work with the Dungeon Master to determine the name and nature of the ship you served upon, as well as what positions you held in the crew. You will also need to work out exactly where you have sailed, if you have sailed around the world, or if anyone ever has. The DM should also work out details about the NPC's in the crew that sailed with you, as well as who likes you and who doesn't.

Skill Proficiencies: Athletics and your choice of Nature or Perception.

Tool Proficiencies: Either the Navigator's toolset or the Cartographer's toolset, Vehicles(water)

Equipment: The chosen toolset from your profession, a lucky charm (roll for an appropriate item on pages 160-161 of the 5e PHB), a set of common clothes, a spyglass, and a belt pouch containing 10 gold.

Alternate Feature: Tribal Customs and Contacts

In your time exploring distant lands far across the sea, you have often had to deal with tribal cultures of various sorts. You know the best ways to approach and communicate with tribals and get to roll with advantage on Insight rolls when dealing with them. Additionally, you have one (plus a number equal to your charisma modifier, as long as that number is positive) contact(s) among the primative human or demi-human peoples that you have encountered. You must work with the Dungeon Master to determine the nature of your contact(s) and what benefits they might provide for you.

Tribal Customs is an alternate feature that can be chosen instead of Ship's Passage (detailed on page 139 of the 5e PHB). Remember that a character may only have one background feature.

Suggested Characteristics

Please refer to the tables below to determine your personality trait, ideal, bond, and flaw.

Personality Traits

d8 Personality Trait

  1. My crew mates know that they can always depend upon me, no matter the situation.

  2. I encourage hard work from those around me and after the work is done I publically celebrate those who clearly put in the most effort.

  3. There is nothing I enjoy more than sailing into a newly discovered cove, disembarking the ship, and setting foot on unknown lands.

  4. When I come into a new area, I'm greedy for information about monster lairs, forgotten ruins, and hidden tombs. I collect all the stories and legends that I can find and record them on my explorer's map.

  5. I have a lesson for every situation, drawn from the experience of many years at sea.

  6. I remain utterly calm even in the face of dire peril because experience has taught me that a calm mind solves problems faster and easier than a clouded one.

  7. I once swam 5 miles in the rain to warn my shipmates that they were sailing into a trap. That swim nearly killed me, but I'd do it again if I had to.

  8. The "right" way to do things is the only way to do things. My attention to detail and shipboard discipline rubs some people the wrong way.


d6 Ideal

  1. Independence - I am free to sail where ever I want. No one ties me down or forces me to do what I do not want. (Chaotic)

  2. Aspiration - I know that I will become the greatest and most famous explorer in all the world and that nothing can prevent that from happening in my future. (Any)

  3. Power - I collect artifacts of magical power everywhere that I go. When I have gathered enough of these powerful items, no one will be able to tell me what to do. (Evil)

  4. Community - We all must put aside our differences, pitch in, and work together if we hope to be as successful as we can be. (Lawful)

  5. People - In the middle of a storm, politics, religions, and philosophies don't matter. When it comes right down to it, only people matter. (Neutral)

  6. Respect - People everywhere deserve to be treated with dignity and respect no matter who they are. (Good)


d6 Bond

  1. I'm loyal to the ship, her captain, and her crew in that order.

  2. My life was once saved by primative tribesmen. I do my best to protect those tribals from the corruption and trickery of the "civilized" world.

  3. You see unnecessary or unprovoked attacks against the creatures of the sea the same as an attack against you personally.

  4. Primative tribesmen love me for my kindness and generosity when my ship comes to visit.

  5. Nothing is more important to me than the crew I work and live with. They are my family.

  6. The cultures of newly-explored lands that I have visited have given me a fresh insight as to how to defeat a great evil growing in the civilized world.


d6 Flaw

  1. I will work until I collapse if that is what is required; I have no time for anyone who does not have the same level of commitment.

  2. I secretly believe that everyone is beneath me and I was chosen by the Gods for a great task.

  3. I never back down from a dare if I believe that I might be able to do it. I don't like to walk away from challenges.

  4. The mere thought of a monstrous and horrible entity that my ship barely escaped from leaves me shaking in uncontrollable fear.

  5. Primatives do NOT need gold or silver; they are too simple to understand its true value. You make every effort beyond outright slaughter to take as much gold and silver as you can from every tribal culture you meet.

  6. You should not expect me to save those who are not strong enough to save themselves. This is the way that nature decides who lives and who dies.

#dnd #DnD #dmadvice #5e #pirates #pirate

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