This is a controversial topic because different people have different opinions on this. However a lot of people have many ideas on the best time to travel.
The only short answer to this would be to book it when it is cheap. However that is not the ideal policy I would stick with. There are many other factors that you at least need to take into consideration.
1) The off-season isn’t the ideal time to travel.
The off-season is the time when the place’s main attractions are closed. Believe it or not, the off-season is not always in winter. Sometimes winter is the best time to go (especially if you are going skiing).
The off-season could actually attract you at first because of the amazing cheap prices. Just go search for the cheapest flight you can find and you’ll find it is in the off-season.
This season isn’t bad just because certain tourist attractions close but also that night-time comes very quick. In fact, where I live, at around late November it will be completely dark at around 6 – 6:30.
However if you are an experienced traveller you may prefer this because of the prices as you will probably not go in some tourist attractions if you already went there.
2) Take into consideration work times.
You should check with your boss or employer and check when you can take some time off work. Even if your request for time off is approved, you should still check and see that the other employees aren’t swamped with work as they will definitely not like it if you leave them all the dirty work while you travel. This won’t be the ideal time to travel.
If you have just recently got hired it wouldn’t be very ideal to just ask for a whole week off if it is a new job. First you need to prove yourself that you are the right person that your employer chose.
Be present in important meetings! If you know that you have an important meeting coming up soon, make sure that you give it a lot of importance, so that the employer will know that you are hard working and you deserve the few days off.
And the most important: Make the most out of your time off! You should spend, ideally, every second doing something fun on your holiday!
3) School days.
If you are a student studying or have children that go to school, then you will need to avoid travelling on school days. Again, this will not be the best time to travel. This is a bit worse and harder to get time-off than it is in work. Usually, they only allow children to travel if they are going somewhere which is necessary (like hospital).
Worse part is that school vacations happen at bank holidays and weekends etc… (with a few exceptions). This means that when your children have a few days of school, a lot of schools will have a holiday too. Meaning that you can find a big crowd if you are going somewhere near (like the beach). What you can do is find those few exceptions (like a founder’s day or another excuse for a day off school) and try and travel at that time if possible.
However if you are not in school and won’t be travelling with someone in school (meaning that school is not a factor you usually consider) you should still pay attention to their schedules and try to travel when they won’t have any days-off to try and avoid the worst of the big crowd.
Plan your trips before-hand
This will help save time and instead of losing sleep at night planning your trips, you can rest and prepare for another awesome day!
However this depends on you. Some people dread doing this mostly because of the time it takes. I love planning because I find the best things to do and it gets me excited as well. It’s all part of the fun.
Another thing I recommend doing is booking everything before-hand if you are eating in restaurants. If you have never been there you don’t know how popular it is.
In the end there are a number of things to consider and usually the cheapest vacation isn’t always the best vacation. Also, there will be a number of incontrollable things that you can do nothing to change them (like weather, work etc… ) However, here is a tip for reading all this (you did right?): I would try to avoid the week between Christmas and New York as it is usually the time when everyone wants to travel.