Hopeful crewmember seeking advice!

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I’m looking to crew a sailboat beginning this November or December. My goal is to live and work on a boat and to see as much of the world as I can until I’m too exhausted or too broke to continue. I’ve been reading listings on cruising websites such as crewseekers, sailingnetworks, findacrew, floatplan, and crewbay, and I have one fundamental question:

What kind of certification should I acquire (competent crew, day skipper, coastal/offshore skipper), if any, before I start contacting skippers/owners or yacht delivery agencies?

I have come across quite a few listings that are seeking crewmembers with little or no experience or certifications. My fear, however, is that I will not be able to sustain a long-term endeavor financially seeking these types of contracts, or that I will run into difficulty finding work against a host of other applicants. Am I better off investing the time and money into proper training and certification and seeking out more highly-skilled positions, notwithstanding my lack of experience? Or would I do just fine getting on somewhere as a deckhand and learning by doing, taking my limited budget into consideration?

I have between 50-100 hours of skipper experience on boats in the 18-24 foot range. I plan on cruising internationally anywhere that I can find meaningful work. My tentative plan is to start in the Caribbean this upcoming winter. I am very flexible on the type of vessel, duration of voyage, and compensation structure.

Any feedback you would be willing to share with an unseasoned seafarer would be so greatly appreciated!
I really can’t give you the advice you are looking for but, as usual, can make a few comments that may be of some interest. To me certifications don’t count for much. That is not to say that they are bad or lacking in any way but rather inclusive. I have a number of certifications in various disciplines but that does not mean that I would be the best choice in one thing or the other. What I look for when interviewing a potential crew member is how they display their knowledge and understanding. Specifically, I give them a number of scenarios and then ask them to explain how they would react to such a situation; I require total detail of every step they would take and why. I question them as to what alternatives they can come up with and why their approach is the best one to take. If they survive a few hours of this questioning and I am still interested I invite them to take a short jaunt out into the water where they display their skills at handling sails and general ship duties. Finally I do a background check on them to make sure they have nothing to hide. If everything goes well they become a prime candidate. There is an unspoken test that they must pass. Specifically, is this a person I can feel comfortable with and I feel is trustworthy? Is this a person that I would enjoy the company of over a period of time? Specifically, do we share common interests? I also evaluate and form an opinion as to their stamina – do they have the strength and energy to perform the tasks that will be demanded of them. I set all of this aside if they are a drop dead good looking girl around 20 years old, blond and are willing to serve me adult beverages as needed… (JUST KIDDING!!!).

Personally, I prefer to sail with Christians; not holier than thou bible thumpers but people just trying to live a good honest life. I keep in mind that there may come a time when my life depends on them and I want to know that they will take care of me just as I will take care of them when the chips are down.

Well, after reading all of this I am sure you still have the same question as you originally posted – sorry, I warned you… Perhaps I should have simply said – different captains have different criterion. If you are on a not for hire sailboat the requirements for experience and formal training will differ from signing on as a deck hand on a commercial vessel, etc. for a container or tanker ship; different for private power boat cursing and working on a tug boat on the Mississippi river. The bottom line is decide specifically what you are looking to do and then start preparing for it. Respond to some of the positions you expect to fill and see what their specific requirements might be. If you are prepared you should not have difficulty finding a gig in the area you want. Be prepared for the compensation to be meals, experience and a free ride with perhaps a few bucks a day. If you find better you will be ahead of the game. The more curses you have under your belt the better opportunity you have to land a “good paying” trip. The docks are full of people looking for a ride from point A to point B so you need to find the right boat with the right requirements.

Good luck –keep us informed as to what you do and where you go…