Tips for Becoming A Good Sailor Taken from Different Periods Throughout History


  1. Become very well-known for your swashbuckling and never hide it. Out-swashbuckle every other man around. Leave no buckle unswashed.
  2. Take what you can and give nothing back. Be a dickhead.
  3. Teach your parrot to say naughty things. It cannot be overstated how important this is.
  4. If you can sing well, then sing. If you can’t sing well, then sing all the time and always be drunk.
  5. Take pride in your plundering abilities. Talk about how good you are at it in every port of call. Maybe plunder something right then and there to prove it.


  1. Find some unique creature of the sea and foster a sharp and sustained hatred for it. The more unique the creature and the more you hate it, the better.
  2. You should be missing at least one of the following things: arm, leg, eyeball, or sanity. In fact, the fewer of these things that you have, the better.
  3. Excel at spotting where she blows. If she be blowing thar, announce this loudly and collect your doubloons.
  4. Know enough about cetology and whaleships to fill at least 500 pages of a 700-page novel. The other 200 pages should be about how much you hate the sea creature.
  5. Find little joy in your dark, thankless life upon the ocean, but always know that someday you will get to kill that sea creature that you hate, which makes it all worth it.



  1. Always tilt your white Navy sailor’s cap to the side. Don’t be a dork.
  2. Get a tattoo of a Hawaiian hula girl on one bicep and an anchor on the other. If the hula girl is topless, more guys will think you’re cool.
  3. Have a pin-up calendar with buxom blondes and redheads hanging in your bunk. Make sure everyone can see it. It cannot be overstated how important this is.
  4. If strangers ask why you’re dressed like Donald Duck, punch ’em real good.
  5. Find random women in crowded areas, embrace and dip them, then kiss them passionately in front of a photographer. Await instant fame and/or a sexual assault charge.



  1. Wear light and breezy J.Crew linen shirts no matter the occasion.
  2. Make sure at least one item of your clothing has an anchor stitched on it. This will help to let people know that you sail.
  3. Always speak slowly, because you are too laid-back from so much sailing to speak any faster.
  4. At parties, tell everyone you meet about every place that you have sailed to. Interrupt other conversations and abruptly change the topic, as they are all secretly dying to know right away.
  5. Wear deck shoes absolutely everywhere.