About Us:

Event.Cruises is a travel agency that specializes in community cruise vacations from conventions to private get togethers. We strive to create memorable vacations by pairing the luxury of cruise vacations with the fun of community events centered around hobbies, interests or personalities. This includes the GACUCON Gaming Cruise, D20 RPG Cruise and Battle Barge Wargaming Cruise with more sailings popping up throughout the year. 

About the Position:

The position D20 Cruise Organized Play Game Master aboard the D20 Cruise is responsible for planning and overseeing organized play activities for Dungeons & Dragons 5th edition experience aboard a 5 day cruise vacation for two groups of players per session up to two sessions on 3 of the 5 cruise days.

This position is seasonal (once a year with chance to expand) and requires remote tasks leading up to the
cruise including selection criteria for Dungeon Master applications, providing 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.


About the Sailing:

The Sailing departs April 27th, 2024 and returns May 2, 2024 to Puerto Costa Maya and Cozumel Mexico  from Orlando, Florida.  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!


Ideal candidate:

One that is friendly, accommodating to all player experience levels and perceptive towards player  interests. We’re looking for professional individuals that are capable of managing several parties aboard the event and cooperating other Game Masters to ensure the guests have a fun and inclusive experience.

If this sounds exciting to you and you believe you’re a good fit 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 two 4 hour sessions for no more than 6 players per table.
— The creation of any Dungeon Master 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.



— Per Diem payment
— Cruise cabin (Shared)  (Roomate referrals or private cabin options available)

— Gratuities paid for by Event.Cruises.
— The sailing includes food, water, tea, juice and coffee at all meal times. Including late night options.
— Surf & Stream Internet package for 1 device paid for by Event.Cruises.
— Ability to promote ones projects/brand as part of the event.




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