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Searching for a new way of life in the boating industry


Amanda’s question

I am a single, laid back, 34 yr old female, that is physically fit, a college grad, and currently living in Florida. I’m seeking a life change and am considering a career in the sailing/boating industry.

I have been sailing most of my life…attended sailing camps in the summer as a kid, and then instructed at the same camp for a summertime job. I have bareboat chartered acting as captain, have basic skills but still have more to learn.

I am considering obtaining my 25 ton master captains license but am finding it difficult to know what life might offer beyond my certification.

I know there are many ways to use a captains license, but I’m MOST interested in chartering sailboats…for a company like the Moorings or Sunsail, etc.

I have a feeling that the sailing world is a lot larger than my current imagination allows, but I’m not sure how to learn more. I’m reaching out to you in hopes that you may be able to offer some advice, insight, or suggestions.

Below are some questions for you:

  • What are sort of opportunities exist in this industry?
  • Is it a disadvantage that I’m a woman?
  • Is it better to be located within the area I wish to work- such as the Virgin Islands – to apply for a job?
  • Is the compensation, in general, enough to live on?
  • Does working in this industry set myself up for an isolated lifestyle?
  • Are there networking sites or job boards?


Gwen Hamlin answers
Gwen HamlinDear Amanda!

 Your letter could have been written by me 25 years ago. I was just about your age when it all began for me.

If you go to my first Admiral’s Angle column, you’ll get a pretty good idea how I got started. No reason for me to type it all up again here.

What are sort of opportunities exist in this industry?

There are lots of opportunities, and unexpected pathways for getting to them. It may be hard to walk up to an island charter company, show a squeaky new captains ticket and expect to get hired as a captain, but you can work your way in.

Is it a disadvantage that I’m a woman?

I never found it an issue being a woman. Neither did most of my other woman captain friends. The trick is simply not to think of it as an issue. Be game to do whatever is needed; if you don’t know how, ask to learn. You’ll be amazed how many of the male charter captains don’t know how to do some of the mechanical stuff, that at least I thought they would have a head start in knowing how to do!

I know some women captains had issues with guests who gave them some grief in not being as assertive as they pictured a male captain would be. I ran into very little if that. I often attribute that to being their dive instructor too. Holding their lives in my hands, so to speak! But mostly, I found, people who will book a boat with a woman captain self select out to being better adjusted people!

The reality of course is that many of the crewed charter boats — whether with the big bareboat companies or private — are run by husband/wife teams, often experienced or returned cruising couples. That doesn’t mean you can’t work without being married, or that you must get pigeon-holed as a chef, but it is a typical arrangement. The good news is that charter boats are getting bigger and bigger and carrying more guests, so there is often a place for a third crew member. In such a situation, keep yourself positioned as an asset and avoid becoming in any way a burden or a liability. Take care to avoid being a third wheel or a threat!

When I was in the biz, I was one of a very few female owner-operators/captains. Other women captains found gigs with single males, some of whom needed paper captains (i.e. The guys didn’t have the correct licenses). Several worked doing captain-only gigs for the bareboat companies. Even with a captain’s ticket, many start out/ or double as charter chefs. Don’t let the “chef” moniker put you off. Just being a good cook can be enough on many boats.

Starting as a deck crew/stewardess is a great way to get sea time as well as inside experience on what is wanted and expected in the charter biz. Every boat and situation will be different, though, and the best asset you can bring is good people skills, natural hosting abilities, flexibility,…..and, like I said, a knack for cooking, cleaning and varnishing doesn’t hurt!

The more qualifications you can walk in with, the better. For the Virgin Islands I believe you would want as a minimum a captain’s license and the STCW endorsement, but you should check with the charter companies themselves and/or the clearing houses for the crewed charter yachts for the most current standards.

If you scuba dive, being a divemaster or dive instructor adds to your options and makes you more valuable. At least be a competent snorkeler.

If you have certifications from sailing organizations that let you teach and/or give certifications, that’s an asset with bareboat companies.

Is it better to be located within the area I wish to work- such as the Virgin Islands – to apply for a job?

Being where you want to work geographically is a huge advantage. Employers in the islands want to know you are committed to being there, that you can take living there! Too many vacationers breeze through with frivolous ideas of stopping to work. But moving there without a job can be awkward if your budget doesn’t allow you to get a place to live while you hunt.

Is the compensation, in general, enough to live on?

Compensation in the charter biz is usually enough to live on because part of the job is living aboard. It won’t make you rich, even (or especially) if you are an owner operator!, but it does afford the lifestyle.

Does working in this industry set myself up for an isolated lifestyle?

You ask if you are setting yourself up for an isolated lifestyle. It certainly was not my experience. There are isolated times, of course, and there are frustrations when your newest best friends — your current charter guests or a cruising boat team you’ve become friendly with — go home or move on. This does not mean the relationships are shallow, they just come and go, and often come back again. There are, of course, sailors, charter teams, and cruisers who choose to keep to themselves, but I would generally consider it a very social lifestyle. It is what you make it.

What you are setting yourself up for is not having a typical life, marriage or kids, pension etc. It’s a fact of life that, as a woman, your window to have children is small, and if that is important to you, you may be making it harder on yourself.

Are there networking sites or job boards?

There are job boards and crew agencies, many based in Ft Lauderdale. I personally think of these as catering to the mega-yacht trade, which is actually another possible way to go. There are all kinds of training opportunities in Ft Lauderdale for these kinds of crew positions. Mega yacht crewing is all a LOT more formal than Virgin Island chartering, and I’ve heard there is bias is against women in deck positions.

There are also boards that match volunteer crew up with boats making passages. This can be a good way to get offshore experience. Many of the major sailing rallies have crew wanted bulletin boards, and our W&C resources page has some suggestions.

Good luck,
Gwen Hamlin
Admiral’s Angle

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