I spent two hours on trial and error and made this lugger.

The name John B is a reference to the Beach Boy's song "Sloop John B", but because the wind physics in SimplePlanes is quite inaccurate, I cannot make a sailboat with triangle bermuda-rigged sails that actually sail in a straight line.

Because the sails are square instead of triangle, this boat would be a lugger instead of a sloop (sad).

This one is without the cannon and the fancy rigging and rudder gizmos.

This one is from above.

Controls:

-Yaw to steer the rudder
-VTOL to turn the sails (search online or ask me about how to rig sails in crosswind conditions if you don't know how to)
-Trim to change cannon pitch
-Act 1 to fire cannon.

Tips:

-Recommended wind speed is 40 mph
-This is a planes game, so sailing isn't very realistic here. The sailboat can't keep moving in a straight line when the wind is coming from an angle greater than 40 degrees to either sides. So try sailing with the wind, not perpendicular or against it.
-For faster turning, play around with the sail angle and you might find a way for it.

If you have any questions on how to use this, please ask, I am more than happy to help. Have fun!