At the northern hemispheres summer solstice, so June, 21st to be exact.
june
In winter.
The sun sets farthest south during the winter solstice, which occurs around December 21st in the Northern Hemisphere. On this day, the North Pole is tilted farthest away from the sun, resulting in the shortest day and longest night of the year. In contrast, the Southern Hemisphere experiences its summer solstice at this time, with longer daylight hours.
The South Pole faces the sun during the summer season for the southern hemisphere.
yes
It's summer in Winnipeg when the South Pole tilts away from the Sun.
Australia experiences summer when the sun does not set at the South Pole. At this time, the South Pole is experiencing its own summer season, known as the Midnight Sun phenomenon, where there is continuous daylight for several months.
solstice
South pole
When the South Pole is tilted away from the sun, it is winter in the Southern Hemisphere.
At the North Pole or South Pole, there is slightly more than 6 months of day, followed by very nearly 6 months of night. The Earth is tilted on its axis with respect to the plane of its orbit. The ends of that axis, the poles, must be either tipped toward the Sun, or tipped away from the Sun. As the Earth spins, the pole facing the Sun is always in sunlight, and the pole facing away has none. Only 1/2 of a planet can be illuminated at a time, and except for twice a year, the North Pole and South Pole are never both in daylight. (This because the solar disc has a measurable width, so that the "top" of the Sun can shine on the North Pole while the "bottom" half shines at the South Pole, twice a year on the equinoxes.)
It is at the north pole that nights are shorter in may. In fact, at the north pole, there is no night (darkness) in May. The sun never sets, but can always be seen at some point in the sky.