D20 Cruise – D&D 5e Dungeon Master Application (Seasonal Contract)

About Us:
Event.Cruises is a growing geek event travel agency. We strive to create memorable vacations and strong communities of travelling geeks. This includes the GACUCON Gaming Cruise, D20 RPG Cruise and BattleBarge Wargaming Cruise with more to come through the coming years.

At the end of the day, we strive to just do cool things for fun people out at sea on vacation!

About the Position:
The position D&D 5e Dungeon Master aboard the D20 Cruise is responsible for planning and overseeing an amazing Dungeons & Dragons 5th edition experience aboard a 5 night cruise vacation.

The Sailing departs April, 27 and returns May, 2 2024 to Orlando, FL. This position is seasonal (once a year with chance to expand) and requires remote tasks leading up to the cruise including your selection criteria for Dungeon Master applications, providing your input for a successful event plan, and setting a budget for resources you need to make this DnD Cruise shine!

The position of D&D 5e Dungeon Master aboard the D20 will be planning and hosting: two x 4 hour sessions of D&D 5e, on a number of days of the 5 days of sailing. In addition to running these sessions, each DM will be responsible for supporting their assigned players. Including but not limited to: character creation, character leveling, or any D&D related requests to ensure the guests have a fun and memorable experience. The staff of Event.Cruises will ensure you receive any support needed to complete your goals and have fun alongside your players! Event.Cruises will be hiring multiple Dungeon Masters for this event.

The ideal candidate is one that is friendly, accommodating to all player experience levels and perceptive towards player interests. We’re looking for individuals that are capable of managing several parties aboard the event and cooperating with other Dungeon Masters to ensure the guests have a fun and inclusive experience. They will handle guest relations, time management, and low-level conflict resolution for rulings as needed. The DM must be knowledgeable of the D&D fifth edition system, specifically the newest ruleset at the time of event.

The Sessions will be most days with planned timeslots throughout various times of the day allowing DMs & Players to enjoy some time off the ship or any number of amenities aboard the cruise ship. Some additional things of note through the D20 Cruise are: World Building Workshops by World Anvil’s founders, painting stations to practice painting tabletop minis, photos-scavenger hunts for prizes, charity and more in the works. The idea is a fun, all inclusive tabletop RPG experience while on vacation. As we say: beach by day, dice by night!

If all of this sounds exciting to you and you believe you have the skills or experience needed to make the D20 Cruise a legendary event for your players then you’re in the right place! Apply and share as much information as you’d like highlighting your Dungeon Master experience and/or why you are the best possible person for this role.


  • Perform for 2 sessions on days 2, 3 and 4 of the 5 day sailing.
  • Assist in the creation of any supplemental content to run it as you see fit including maps, terrain, stories, trinkets, etc.
  • Utilize Dungeon Master Safety Tools and ensuring adherence to the event’s Code of Conduct for yourself and players at your table.
  • Build a list of required materials or content required to successfully run the activities. This includes things needing to be printed out, require internet access, etc.
  • Manage guest issues on site with no-shows, table changes, starting and ending sessions in a timely manner.
  • Manage player issues calmly and quickly to continue playing as much as possible, then escalate any larger issues to the Organizers or Event.Cruises Crew for any other disputes as needed.
  • Act as an arbitrator for rules and resolve low-level conflicts between guests should any arise.
  • Assist in the final selections of modules, mini-games, homebrew, or other content requests by the Event.Cruises team to enhance the event. Your opinion to enhance the event is encouraged!

If selected to set sail as 1 of many [D&D 5e Dungeon Masters] for the D20 Cruise here are some considerations/benefits:

  • Per Diem
  • Split cabin with other crew DMs (Or equivalent paid for private cabin)
  • Gratuities included
  • The sailing includes food, water, tea, juice and coffee.
  • Internet package for 1 devices
  • Ability to promote ones projects

"EC_Dru is one of the co-founders of Event.Cruises including GACUCON Game Cruise, D20 the RPG Cruise and Battle Barge the Wargaming Cruise. He's travelled the world and dragged his hobbies along with him as a game master, painter of minis and most recently a 3d printing adept. You can find him @CruiseDru on Twitter."


  • James Reply

    If I am selected as a DM, can my wife get the same room if we pay for her to come as a guest?

    • ecdru Reply

      Yes! We allow event crew to upgrade to bring friends and families or just stick with the staff cabins.

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