Pineapple express weather is good for people who walk to their cars with an umbrella. 11 degrees C in January indisputably beats being in some snow blizzard in northern Ontario. Look how much better off we are than those suckers, ha ha!
11 degree water, on the other hand, is like out of the cold water tap. Not so great for outdoor activity. Add to that the windchill factor if you're running or cycling.
Clear, sunny weather and -3 degrees is better than pouring rain and 11 degrees.
Staying warm isn't much of an issue for outdoor activity. It's not hard to achieve: an extra layer, some head gear and gloves; being dry is more important.