There are plenty of things that one has to consider when deciding when to go take a vacation. This entry will try to enumerate them.
First of course, is when you can get time off from your schedule. Of course, not all of us are vagabonds, spending months or even years on the road. The majority of us travelers have a stable routine, a job, a rhythm, that needs to temporarily stop if we want to get a vacation. So consider that first.
Aside from that, the most important consideration I suppose is the weather. Having a bad weather can definitely spoil your vacation, if that is not supposed to be part of the equation. So research the weather patterns in your destination of choice, and plan accordingly. You would not want to go to the Caribbean during hurricane season. Or you might want to avoid North Africa during the summer, as the heat just is unbearable. In some countries, the weather can be tricky. Ecuador and Peru for example, have different weather systems depending on altitude, so seaside cities like Guayaquil and Lima have a different pattern from Andean cities like Quito and Cuzco who in turn have a different pattern from Amazonian cities like Iquitos. So check the weather of the place that you are planning to visit.
The tourist season can also play in the equation. Generally, airfare is cheaper if it is the tourist low season, which is from January to early May, and from September to mid-December, at least for North America. The high season usually corresponds to Christmas travel, and the summer school break.
This is not always true, however, due to the fact that there are some spots that can have outrageous fares and hotel rates, such as holidays. Mardi Gras for example is a high season in New Orleans. So is certain Fiestas in Latin American countries. So think of this when planning your trip. This would be especially of note if you are doing some internal travel. If there is a huge event in town, chances are you would have a hard time getting around; the buses to the next town might already be full, and you might end up stranded in your hotel.
Things that are similar in nature also include periodic closures of sights, such as annual cleaning, and so forth. So do not plan to hike the Inca Trail in Peru in February, because it is closed for the annual cleaning. Do not visit Taos Pueblo in New Mexico during March and early April for the same reason. They will be closed.
Some people, like me, for example, prefer that the destination be devoid of tourists, when I visit. I therefore watch out for tourist high seasons and try to avoid them. Case in point: 3 years ago, I was in Rome during May. The lines entering the Vatican City Museums were winding the block, and one simply cannot appreciate the Sistine Chapel with too many people like that. The marble floors acted more like treadmills instead of leisurely walks, and the space simply was cramped. If you want peace and quiet, then stay away from the tourist high season and you’ll have a better time enjoying the scenery.
Another benefit of visiting places in the low season is that you will spend more time learning about the places you visit. If there are plenty of tourists, the museum tour guide would be less likely to answer your questions, since they would rather finish processing you and move on to the next batch of people waiting. However, if the visitors numbers are low, then the process gets more interactive, and having the extra time allows the guides to bring out the personalized touch that most of these people have. In Quito, I was in the house-turned-museum of Ecuadorian artist Oswaldo Guayasamin, and at that time, there were only two of us visitors, the other was an American grad student, and we basically had the place to ourselves. The museum guide, even though her English wasn’t very excellent, was warm, and I felt like I knew a lot more about the place than what the regular visitor would experience.
So there, that’s my latest dose of Independent Travel 101. Stay tuned for the next update.