It depends on where you go.
For me, the first two weeks of December is the best time to go to the tropics. Because it is a relatively low season and many of the travel agencies are offering deep discounts.
In Canada, I like to travel in June and late September and early October. Because these seasons offer the best weather and scenaries.
I never travel for vacations. All I know is that it stinks to drive in the winter with all the snow & ice where we live, so I try to stay even closer to home than usual during that time.
I would say all seasons are good but I try to avoid extreme hot and extreme rainy /monsoon periods.
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