Student?

Travelling while a student or while 26 years old or under, often makes you eligible for very significant discounts.

Peak season?

There are often benefits travelling to popular destinations just before or after peak seasons. These include reduced queues in places like Prague or Venice, avoiding a 2 day wait for a spot on an Alcatraz tour in San Francisco. But remember, high seasons are often popular for very good reasons.

Timing is everything and can make all the difference. For example:

The Japanese cherry blossoms only bloom for around a week starting in the south around early April. So why not start in the south and follow the blossoms, festivals and partying north, turning 1 week of celebration in to many.

Transportation in Australia's northern regions during the (Australian) summer/wet-season can be difficult due to swollen rivers and wetlands, and continual torrential rain.

Hostels and tourist attractions are often closed or scaled down during winters in colder countries.

Alaska only has a 2 or 3 month window in the North American summer where travel is comfortable.

Working?

Beware of new year market slumps, typical in many industries. Always investigate arranging work before arrival but be careful of agencies willing to exploit your unawareness of the markets they supply.