Leadership lessons learnt from competitive sailing

Glossary of sailing terms

My goal is to write for as wide an audience as possible and I’m assuming no sailing knowledge. Sometimes I will use sailing terminology which you might like to understand a little better. I’ll try to add to this list as required - please let me know if I’m missing something.


  • Upwind: the direction the wind is coming from - the opposite of downwind
  • Downwind: the direction the wind is blowing - the opposite of upwind
  • Port: the left hand side of the boat
  • Starboard: the right hand side of the boat
  • Regatta: a series of races - typically over consecutive days

Types of boats

Not an exhaustive list, though these are the ones I will refer to:

  • Dinghy: a small sailing boat which is generally single or double-handed
  • Skiff: a high-performance sailing boat which achieves high speeds. Generally skiffs have 2 or 3 crew members depending on the class
  • Keelboat/Yacht: A yacht, which has a chunk of lead on the bottom to stop it capsizing
  • Maxi: A large yacht. It’s as keelboat, just bigger and with more crew
  • One-design: all boats are of identical design and construction - this can be any of the above types of boats


  • Tack/Tacking: when the boat is changing direction and as part of the manoeuvre the bow passes through the wind. Initiating a tack requires you to point the boat closer to where the wind is coming from. In order for a sailing boat to sail upwind, the boat must sail at an angle from the wind and perform a number of tacks.
  • Gybe/Gybing: the opposite of a tack. When the boat is changing direction and as part of the manoeuvre the stern passes through the wind. Initiating a tack requires you to point the boat further away from where the wind is coming from
  • Luff/Luffing: pointing closer to the wind
  • Bearaway/bearing away/footing/sailing lower: pointing further away from the wind
  • Capsize: when the boat falls over - you want to avoid this
  • Nosedive/pitchpole: when the front of the boat goes under water and the boat comes to an abrupt stop - spectacular though best to avoid this
  • Aground/hitting the bricks: when the water is too shallow for the boat and it hits the bottom - you want to avoid this

Parts of a boat

  • Bow: the front of the boat - often shortened to front or the pointy end
  • Stern: it’s the back of the boat - often shortened to back, ass etc.
  • Mast: the tall stick which sails are attached to
  • Boom: the horizontal stick which swings across the boat at the bottom of the mainsail
  • Bowsprit: the stick which pokes out the front of the boat - not all boats have bowsprits
  • Rig: the mast and the stays make up the rig
  • Cockpit: where the majority of the crew operate, towards the back of the boat
  • Halyard: these are the ropes which pull sails to the top of the mast
  • Sheets: these are confusingly the ropes which control the back corner (clew) of the sails (main, jib, spinnaker)
  • Stays: the cables which hold up the mast

Sails & bits of sails

  • Mainsail: The large sail at the back of the boat - often shortened to main
  • Jib/headsail: the smaller sail infront of the mast - sometimes also known as a genoa if it’s larger in size/there isn’t much wind
  • Spinnaker: The big colourful which is set off the front of the boat when sailing downwind - often shortened to kite or chute
  • Clew: the bottom back corner of a sail - on a symmetric spinnaker it will have 2 clews
  • Tack: In the context of a sail, the tack is the front bottom corner of it. See also tack under Manoeuvres
  • Head: It’s the top corner of the sail


With many smaller boats & keelboats, one person may take on multiple of these roles - note the parallel with startups and smaller businesses where staff often perform multiple roles.

  • Skipper/helmsman: the driver of the boat - sometimes on very large boats skipper and helsman are different roles and the helmsman is the driver. I’ll always use skipper and helmsman to mean the same thing.
  • Trimmer: person who is responsible for adjusting sails. They work closely with the skipper. On yachts there are often multiple trimmers:
    • Mainsail trimmer: they trim the mainsail (the big sail at the back of the boat)
    • Headsail trimmer: they trim the jib/headsail (the smaller sail at the front of the boat)
    • Spinnaker trimmer: they trim the spinnaker when sailing downwind - often the headsail trimmer will switch to spinnaker when sailing downwind
  • Navigator: they decide where the boat should go - typically longer-term focused and a role seen in ocean races.
  • Tactician: they decide where the boat should go - typically more focused on short-term tactics during tight racing. Works closely with the skipper.
  • Bowman: The bowman is the crew member who operates at the front of the boat. They are typically nimble and adventurous. On larger yachts, they will often be hoisted up the rig if required for repairs etc.
  • Pit: on keelboats, this person controls the halyards and are critical for hoisting and lowering sails. Works closely with mastman, bowman and a role within the cockpit which is coordinating manoeuvres
  • Sewer: on keelboats, the sewer handles logistics below decks - predominantly sorting & packing sails
  • Mastman: on keelboats, the person who operates at the base of the mast - ensures sails are hoisted quickly, works closely with the bowman and pit
  • Shore crew: professional teams have shore crew who handle logistics, boat preparation, boat repairs, sail design, fitness, nutrition etc.


  • Gust: a burst of wind which is higher in velocity - very short-term in nature
  • Lull: a sudden reduction in the strength of the wind - very short-term in nature
  • Shift: a change in the wind direction
    • Oscillating: a change in wind which oscillates back and forth
    • Persistent: a permanent shift in the wind direction
  • Strong/windy/fresh: it’s windy
  • Light: there is a little bit of wind, however, it isn’t very windy
  • Drifter: there is no wind, the water is glassy
  • Dirty air: disturbed air from another boats sails