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Northernmost: Montreal, Quebec, Canada. About 45.5 N.
Southernmost: I wasn't quite sure. Had to look it up among the places I've been to. Belize City, Belize at about 17.5 N beats out San Juan, Puerto Rico; St Thomas, US Virgin Islands; and Tortola, British Virgin Islands, all right around 18.5 N.
Taking seasons into account:
Summer, same as above.
Winter:
Southernmost: Kiawah Island, SC, this past December. About 32.5N. It was mostly coolish. This was between Christmas and New Year's, and at the time, it was very noticeable how much longer the days were. The sun was only setting around 5:30pm, compared to 4:30ish back home. So much greenery. I enjoyed this trip a lot.
Northernmost: Peterborough, Ontario, Canada: about 44.25N. Actually mid-March, so really more like the end of winter. Drove there to visit a friend a back in 2011. The day I got there it actually so sunny I had to use AC in the car. Only patches of snow left when I got there. The day I left it had snowed a few inches overnight and I got to have fun driving around in it shortly after sunrise. In the middle of winter (mid-January), the farthest north I've been was Toronto (about 43.75N) in 2010. There was snow on the ground when I got there that had melted by the time I left a few days later.
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