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A sailboat cannot sail directly into the eye of the wind, but can sail to within
45 degrees of the wind or closer when close-hauled. If you head into the
wind, your sails will start luffing and you will lose power and the
ability to steer. Describing a sailboat's course in relation
to the wind direction, the points of sale on the right
show a starboard tack and assume that the
wind is blowing from the top of your
screen. Boat drawings and info from
me and Chapman Piloting
and Seamanship,
65th edition
by E. Maloney.

• Run

  When the wind is almost directly behind you, the boat is said to be "running". If the wind is light, it'll feel like you are not moving but just look behind the boat and you'll see a rippling line of water.

• Close-Hauled

  When there's the smallest angle between wind direction and heading, the boat is said to be "close-hauled" meaning that it's sails are pulled in close to the boat.

• Close Reach

  When the angle between heading and wind direction is increased, the boat begins to "close reach". A close reach is somewhat toward the wind, and broad reach is a little bit away from the wind. Fast point of sale for most boats. The sails are eased about halfway out.

• Beam Reach

  The boat is "beam reaching" when the wind is on the beam at a right angle to the boat.

• Broad Reach

  Further increases to the angle between heading and wind direction (more than 90 degrees) bring the boat to a "broad reach"