shoestrung:

shoestrung:

About seven months ago now I walked down a dock in April and tried to
guess which of the three shrinkwrapped schooners docked there was going
to be my home for the foreseeable future. Coming out the other side of
the season, I’ve got hands like leather, killer biceps, a general
familiarity with sailing, two near-death experiences, and in general I’m
pretty comfortable wearing a knife around now. This is going to be a
quick breakdown of the ups and downs of windjammer life, because I sure
as hell had no idea what I was getting into, and if it sounds like an
interesting job maybe you can go into it a bit more prepared than I was.

Windjamming
– the part of the traditional-rigged sailing industry that deals with
tourists, and the focus of the guide. Generally to do anything else with
tall ships, like deliveries (moving a ship from point A to Point B,
like the Florida Keys to Boston in time for the summer season), you need
to have some sailing experience already.  Windjamming can be split into
day sailors and longer cruises.

• Day sailors
  make 2 to 4 short trips a day, generally in the area of three hours
  each. The tips are better because you see so many people in such a short
  time. You’re in port every night, so you’ll always have access to cell
  service, grocery stores, the bars, etc. You tend to have rainy days off.
  On the flip side, it’s not always a live-aboard position, so if you’re
  hoping to be staying on the ship, make sure you ask. You’ll also be
  feeding yourself out of pocket. The repetitive nature of the trips can
  be monotonous, and you don’t really have a chance to get to know the
  guests. Generally smaller boats and smaller crew.
• Longer Cruises make
  overnight trips, generally 3-6 days, which means they go further and
  there’s more variety in where they sail. You get to know the passengers
  much better, and you really get to see the breadth of weather on the
  ocean – it’s a much fuller experience in terms of sailing. These are
  almost always live-aboard positions, so you have a home with no rent to
  pay. You’ll be fed as well as the passengers are, and even on the days
  you’re in port, there will be leftovers to eat if you don’t want to
  spend money – you can save a lot more because virtually nothing has to
  be spent on the cost of living. On the other hand, you’ll be out of
  contact for days at a time, and the unending nature of the job – with
  guests aboard, you’re responsible for their wellbeing even when not
  actively on duty, which can mean up to six unbroken days of Customer
  Service Face – means that it can be emotionally a bit overwhelming at
  times.

Pay varies pretty greatly from one
boat to another; for the entry-level position of messmate, I’ve seen
anywhere from a pretty generous $400/week to volunteer. Those seem to be
the extreme ranges of the spectrum, so anywhere in that ballpark could
be expected.

Positions open to you as a total beginner are:

• Deckhand
  – a standard sailor. Usually you need a bit of sailing or
  sailing-adjacent experience, but not always, if you’re strong and quick
  to learn. Duties tend to include tacking, furling, and reefing sails,
  cleaning the ship (deck, the toilets, the sides of the hull, etc.),
  helping passengers up and down the ladders, and similar tasks.
• Cook
  or assistant cook – day sailors don’t have this, so if you want to work
  in the galley you’re going to have to commit to a longer cruise.
  Planning and preparing all meals, three times a day, for about 30
  people. Often includes things like baking your own bread. might be on a
  wood stove or a propane stove; sometimes the stove swings to stay level
  and sometimes it has fiddles to keep pots from sliding off, but not
  always. You’ve got to be an early riser, and good at time management.
• Messmate:
  another galley position, but this one is half-way between the galley
  and the deck – ideally a 3/1 ratio. Cleaning dishes, setting tables,
  assisting the cook on occasion with meal prep, maybe snacks and things
  like that, as well as small things on deck like tacking sails. A lot of
  that is on you, however – go bug deck crew to teach you if that’s where
  you want to be.

Life on a windjammer/General things to know

• Pack
  practically. I really can’t emphasize this enough. You’ll have a few
  days off but you’re not going to have the energy to get into nice
  clothes and honestly you’re going to be covered in paint dust/anchor
  grease/pine tar/whatever the fuck anyway. You really won’t have any use
  for anything besides working clothes and mayyyyyybe one nice outfit to
  remind you that there were better days, once. Bring clothes that you can
  burn at the end of the season, because they’re not going to be wearable
  in public.
• Get a pair of work pants – Carharts, Dickies,
  doesn’t matter – as long as they’re tough as hell and have a lot of
  pockets. You’re also gonna want to have a leatherman, or ideally a rig
  knife/marlinspike set (cutting lines, tightening and undoing knots, etc.
  are things you’ll find yourself doing frequently).
• Learn
  how to tie a bowline, a cleat, and a rolling hitch. You can learn
  everything fancier, but these are the three you’ll be using the most.
• Just…give
  up on ever feeling clean. Life is easier that way. You can get a shower
  and wash laundry on land, but while on board it’s lucky to have hot
  water, and you’ll still be washing your hair in a swimsuit, on deck,
  with dish soap. Embrace it, bring deodorant, go swimming in the ocean.
• Some
  really weird jobs are going to be given to you. Sailing, cleaning,
  whatever, all in a day’s work. Rubbing down all seventy feet of the main
  mast with Vaseline while being belayed down on a swing also
  covered in Vaseline…a bit out of left field. Windjamming is basically
  an endless string of crises, so don’t be too thrown when something goes
  wrong.
• Ideally you’re reasonably good with heights (if not, avoid ships with topsails) and don’t get motion sickness.  
• There’s
  a lot of turnover – people leave all the time for all kinds of reasons,
  like going back to school in the fall, getting hurt, getting fired,
  getting overwhelmed and quitting.
• It’s a gift culture – your
  crew is what keeps you going, and you share what you have – people with
  real apartments will offer you a place to sleep and shower. People
  who’ve done this before will give you things you’re missing. Things like
  hats and books and jackets get traded and gifted a lot. Over the course
  of the season I gave away hand cream, a coffee mug, rides to places in
  my car, drawings – not much, but I didn’t come with much that could be
  useful. I was given a rig knife, a ceramic bowl, a few books, tea, a
  ukulele. Share what you have and give away things someone needs and you
  don’t. 
• You’re going to meet a lot of weird people. Well-balanced people with 9-5 jobs who are content with their lives and like doing things like ‘leisurely sipping coffee in caffes while it rains outside’ and ‘bathing’ don’t often apply. If this is the kind of job that appeals to you, then it’s likely they’re going to be your kind of people.
• There’s definitely a drinking culture, but there’s no pressure to join in, in my experience. Everyone is really chill  about whether or not you’re drinking; often the local dive bar is simply the closest warm place to find people and touch base with the other schooner bums. Once in a while someone will buy everyone a pitcher to share, but this is more related to ‘share what you have’ than to ‘everyone must drink’.

That’s it off the top of my head, but please
feel free to message me if you have any questions! I can’t promise I’ll
have a good answer, but then again I might. Hope this helps!

Some more things to know!

Finding a job

• Tall Ships America billet bank has some listings, which change pretty frequently as the seasons go on, so keep checking if you don’t find something that appeals to you the first time round.
• Honestly, though? The industry is largely word of mouth, and so many captains/owners don’t actually advertise. Your best best is to look up windjammers in an area you want to work out of (Camden ME, Newport RI, and Mystic CT, off the top of my head, are some windjamming hubs where you could start to look; Baltimore is one, so is Boston, and there’s definitely some West Coast ships, although I’m less familiar with that. Winter season is in Florida and the Caribbean).
• Just send a fuckton of emails. Carpetbomb the industry. Once you’ve got the emails of a dozen or so captains, go ahead and email all of them to see if they have a position open. If you time it right (the summer sailing season starts hiring Jan/Feb; winter in Aug/Sept) then you’re going to find something. 

Something else – your hands are going to be hamburger for the first few weeks of working line. They’re gong to get dry and cracked and callused and it’s gonna suck. Then they’ll toughen up and you’ll have grown your gloves and it’s all fine again, but be ready. O’Keefe’s Working Hands hand cream helps a bit.