A Pirate's Life: A Crash Course To Suriving Your First Cruise Ship Contract (tenative)


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Why am I writing this book?

To start, I’m not what you'd call a cruise ship person. It's always struck me as the domain of families, the elderly and young adults who should learn to get drunk on a week day so they can better handle their liquor. On top of all that, cruising always struck me as something people who don't really like traveling do.  I have an affinity for water but I can honestly point out that it’s never been a dream of mine to actually work, live and play on it. Until I got the job offer. THE job offer. The job offer that I didn't even know I was looking for.  Through some crazy calling from the depths of the universe, one of my Facebook friends messaged me about a position on a cruise ship involving one of my other favorite things to do for fun and profit which is being a DJ.

As a DJ I've dealt with my share of janky promoters, shady bar operators and all sorts of people who'd act like they had your best intentions at heart only to twist the proverbial knife in it when there was money to be made. I don't keep in contact with those people now but I wasn't too keen on playing the "hurry up and wait" game with them when I could be out expanding my audience and experiences (you wouldn't be reading this in any case).

In my situation it was the ability to move out of the back room of my grandmother’s house as well as a deviation from a job that was easy and taking care of things but not doing enough for me as far as my post-grad adult life. I was working IT at the university I graduated from as well as part-time DJing where ever and whenever I could. A Bachelor's Degree was obtained but that was only a back up plan to make the music business that I really wanted to do work.

When I was first told about the opportunity my first thought was "How could I pass it up?". I don’t have a history of getting seasickness and it’s not like I’ve ever been on a cruise ship before it was offered to me as a job. Who was I to say no to opportunity? After getting the medical examinations and job applications done I was playing on ships from the Bahamas to Belize, South Beach to Sydney and took very little (if any) time off in between.

There are innumerable benefits to cruise ship work, especially if you're in the Entertainment Department. Think about it. Travel. Adventure. A salary to do what you've been going to all these rehearsals and side gigs to do anyway, which is perform in front of people. Speak. Interact. Build relationships. Network. And if you weren't involved in entertainment before, no worries there. I know guys who weren't what you or I would consider great public speakers turn into master orators from all the experience they've had hosting ship activities. I've seen girls go from really good shower singers to full-blown vocalists on par with some of the hottest acts on the globe. You could EASILY join their ranks with some legwork and openness to learning.

I worked about 400 days total on board four VERY different cruise ships, all for the same company. Yeah. I was hooked. I barely took more than a week off in between ships for that year because the lifestyle was just that thrilling to me. Even with all the safety procedures, management and guests seemingly always watching me; feeling utterly disconnected from "the real world" and learning everything as I went along, taking detailed notes where I could and jogging the hell out of my memories when I couldn't. Imagine a baby learning how to crawl, then walk, then run. The process of how I learned a ship's layout was similar to that in pacing but with me running into a lot of walls head first along the way with not a helmet in sight. When it was over I was looking for the best way of answering the age-old question that every person who's ever worked aboard is asked when they return to land or more than likely while they're AT work on board "So. What's working on a cruise ship like?". My answers averaged between really brief or really detailed at first, the distance between myself and the cruise line helping me to reflect on everything I've done on those four ships. Then a thought occurred to me one day in a Miami bookstore; if I was setting out on a journey like this for the first time or never even set foot on a cruise ship, what would I want to know in order to navigate it and kick ass at my job?

That’s where this comes in. It was a challenge as to whether I wanted to make this a “how-to” guide or a personal book detailing my adventures because, marketing. I found that there aren’t many (if any) books detailing this sort of lifestyle and there’s no one better to tell you what you're in for than the man who lived, learned and maneuevered all of this for 13 months AND survived it all with his sanity intact (his wallet was fed to the fishes but it’ll resurface soon enough). That man is I. I’m still DJing but in a land-only capacity with some charter ship work here and there. Thanks to my year at sea I got the chance to enhance my skill-set, interact with people from places I can’t easily find on a map, do some incredible things (Skydiving 14,000 feet in Fiji with a magician. For starters.) and  now writing a book on the subject. That book is what you’re reading now. And no, it is not smooth sailing from here. But that’s the fun part.

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Why Cruise Ships?

Why Entertainment?

Working with talented people in front of diverse crowds.

Most skill variety (management of people and time, public speaking, builds atheticism)

Most privleges, time off and social perks, BEST PAY (and way to save money)

Demo Tape (You want me to do WHAT?!)

- the people who entertain are there for a reason.

- what they're actually looking for (DO NOT BE BORING).

- agents help. I know of many musicians who use agents to get aboard. (Ask Sean, Mike, Zorro, Mikey about this)


Before I get to the "what's right and what's in it for you" it's only right that I dispell a few popular myths about the working experience of cruise ships with my ACTUAL, non-disgruntled working experience.

  1. Once you sign on, you stay on the ship and can't leave until the contract's over (wrong. conditions might be a little unconventional but you DO get time off. how you use it is a personal matter but cruise ship personnel get off of the ship EVERY CHANCE WE GET. As far as contractually, where you're assigned doesn't matter because it isn't stated. some people can do 3 or more ships in a length of time. Both of my contracts had me on two ships at a time. And you can always transfer to other ships like you would other offices in your company)
  2. You're on call 24 hours with no break (depending on your position, this might actually be true but your breaks are whenever you're not working. just remember to clock out)
  3. Low pay, there's no money in it (offset by the fact that you don't pay for room, board or food as long as you're signed-on directly with the company. also based on department.)

What people want out of a vacation

When people speak of vacations, visions of pristine beaches and white sand are the go-to imagery. It's all painted as this santized, safe wonderland that's not too dissimilar to your friendly neighborhood playground. That's good marketing at work. The reality of vacation is that you're just not going to work for the week and making the decision to spend time in more interesting places than the bar down the street on a Saturday. Coming to a beach when you live nowhere near one counts as a "different" experience.


What you're getting paid to do as an entertainer

  1. Definition of "entertainment" via Webster's
  2. You're always selling something (the experience, yourself, alcohol via your craft)

Your Clientele

50 states, 50 different ways of doing things.

Kids and Families. Think of a Disney Park. Retirees.

New Yorkers - loud, obnoxious

Midwesterners -

Southerners - Mild-mannered, crass

Rest of the world as well.

And Australia's like all of these combined but they're way more generous at the bar and more about watching the entertainment than participating in it.

Easy way to jumpstart your career

Deliberate practice is the key to improvement. Your work life is going to be a book called "Deliberate Practice For Profit"

Time is on your side


What to expect when you're expecting

So. The job application is filled, your medicals marked you as fit for sea duty and you're ready to roll! Now you wait for a ship assignment. As you wait for the travel gods (or shoreside management)  to make a decision where to fling you off to, consider these things while getting ready for the adventure:

  1. How long should my contract be?
  2. Will I be able to communicate with people back home from where ever I am?
  3. What should I bring with me that I might not be able to get later? And how much clothing is too much?

To answer the first question, it depends on how long you're planning to sign on for. Most contracts can range from anywhere from 2-10 months (because sign-off dates can change on a whim or situational basis). So ask yourself "How long do I want to be away from home? Is there anything happening that I NEED to be home for coming up soon?".

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Joining the Circus

Training (2 weeks)

The Best Analogy Ever

Cruise voyages go by many, many names not all of them nice. "Voyage of the Damned" this "Booze Cruise" that. One of my musician friends gave me an analogy that encompasses every bit of the cruise ship working experience.

The analogy: living on a ship is like living in a hotel/college/navy/pirate ship/insane asylum/circus

What do these things have in common?

Each of them is a self-contained world with its own experiences to learn from. They all have their own rules, regulations, gatekeepers and hierarchies. If you consider yourself a "normal" person, you might not last too long (save college). Cruise ships tend to attract a few kinds of people


Sign on procedures

  •  learning your way around, who to meet, who to stay away from, etc.
  • Money. Adventure.  Running away from something… or towards it.
    -- you get better by being thrown in into new situations and trying new things.


"Is The Philipines in the house?! Any one not from the Philipines in the house?"



- the hours are long, the guests come in every flavor you can think of…
- time management is EVERYTHING

- disconnection from the real world can be a pain.

Before we get to the ooh's and aah's and on-board stuff, let's go over who this ISN'T for.


So, the routine depending on ship itinerary on any given day;


Embarkation Day

A day unlike any other… but like so many others. This is where old passengers (crew, guests and otherwise) leave the ship to go somewhere else and new personnel join up. The home port serves as either the one place you'd rather not go back to because it feels like a never-ending Monday at the office or as a relaxing break from being out of touch with the "real world".

Good home ports: Charleston, SC. Miami, FL. Sydney, NSW, Australia. Tampa, FL. Galveston, TX. New Orleans, LA. Long Beach, CA.

Ports get used to collect supplies and personal items for the upcoming voyage, connect with family and friends and in my case get something to eat while chatting up locals.

The actual "grind" of Embarkation Day starts when you get to work, usually around 11am. Work consists of being informative and entertaining and most of all, helpful. Most asked question on Embarkation?

"Where's the food?"

As a man who has chosen his profession to be that of playing songs to set up a vacation atmosphere, everything I do or say goes towards maximizing the experience. In the USA I'm on the microphone selling people the dream that they've saved all their hard-earned ducats for. "Ladies and gentlemen, children of all ages!" and the like. I go for a live show feel mixed with performance theater just to envelop passengers into this reality we're trying to create. It's barely about mixing the music (I'm one of the only people I know who admittedly cares about good DJ mixing on a cruise ship. Really). What I'm encouraging is an overall "fun" vibe. Something like when you introduce yourself to someone you WANT to get to know. Keep it fun, keep it light-hearted and let them connect with you on one level or another. Harder and easier than what I'm making it sound like.

This atmosphere continues until the safety briefing in which I or other crew members show you how to save your own life in case an iceberg hits the ship in the middle of a tropical cruise. People worry about these things. After the briefing comes the deck party where the Entertainment Staff (DJ, Cruise Director, Assistant Cruise Director, Hosts) all team up to set the standards for what may very well be the greatest vacation you've ever taken in your life. Yes, even better than that out of town trip you took where you woke up with a tattoo on your face and a tiger in your bedroom.

Living Arrangements

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No Business Like Show Business

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You Are Not Your Nametag

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No Days Like Sea Days

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Another Night Out

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Ship Relations or Relationships?

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We’re ALL in Customer Service

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No, this is REALLY my last contract!

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Tips, Tricks, Cheat Codes

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