Travel Planning: When To Go?

Planning a trip for me really begins when I pick the dates for travel. Having a cemented time line to work from means for me that the trip is actually going to happen and it also works to implement a deadline. Choosing when you want to go to your destination can be dependant on weather, events or festivals, weddings or other conflicting events, or even travel prices. There is a lot to consider, which can easily be a hang-up for people.

NYC in late August- Rainy but less crowded.

NYC in late August- Rainy but less crowded.

I like to plan well in advance so I can mark off time on my schedule so our trip won’t wreck havoc on my clients. This gives me plenty of time to scout what the weather will be like and what there will be to do during that time frame. It also gives me a heads up of where not to go if there are going to be events drawing large crowds that will interfere with our trip. It might be cool to visit Milwaukee during SummerFest, but imagine the crowds and how annoying it can be if you aren’t anticipating them.

A great place to start planning when to go is to check out the State and city tourism websites. You can usually search by month and see a calendar of upcoming events, often linking you directly to the event page. When we visited Minneapolis, we didn’t know the Aquatennial Celebration was happening, but we got to enjoy some late-night fireworks on our last evening in town and it was a trip highlight. If we hadn’t stumbled upon this event, we would most likely have been unhappy with the ridiculous crowds and noise, be we embraced the fun. It’s also good to know how events will impact visiting museums, specific restaurants, or public spaces you might want to see.

Rainy weather in the Caribbean

Rainy weather in the Caribbean

Weather and the time of year can also impact your travels. Disney might sound awesome for spring break, but high prices and long waits for rides are an immediate turn off for me. Obviously if you are planning a trip for the same time that everyone else is, Spring Break, for example, then you really don’t have a ton of options in the time frame section. You might be better off looking for a less-visited area or a more off-the-beaten-path place, but more on that later. Marcus and I decided to go to Italy for 2 weeks at the end of September, when tourism was slower, weather was cooler, and prices cheaper. For us it makes sense to go to destinations off-season as we are budget travellers and we don’t care for heavy crowds when we visit places.

We took our first cruise with Carnival several years ago and booked for the first week in January. Great prices on our cruise, not so great for the flights, but we still paid less than we would have for most of the year. If you are willing to risk bad weather or rather, unpredictable weather, you can usually get a good pay-off in terms of cheaper prices.

Here’s a breakdown of how I choose a date for our travels:

  • Month- What is the weather going to be like, too hot or too cold, rainy or windy? What do we want to do on our trip, and will weather negatively impact our plans? Is there a season we specifically want to travel during?
  • Week- Are there any family obligations to avoid? Are there any holidays to plan around (we don’t tend to travel around holidays as everything is more expensive)
  • Day- travelling during the middle of the week is cheaper. Flying on a Wednesday can save you big money over flying on a Saturday. The same goes for hotel fees and attractions.
Jersey Shore in October- people-free beach, beautiful Fall days.

Jersey Shore in October- people-free beach, beautiful Fall days.

Obviously if you are planning a trip for say, New Year’s Eve in Times Square, you are kind of locked into a very specific time frame, but you can still plan your travel time to help save money and to also maximize the benefits of the trip.

As I mentioned before, setting the date for a trip is my first priority, but it is not done without a lot of research before hand. I usually know when hotel rates, airfare and attraction rates are higher or lower before I nail down a date. That being said, I always finalize the date before moving ahead with any other plans that require a commitment or purchase like renting a car or hotel room.

Hopefully this has helped show you some of the techniques I use to determine when our specific trips are planned for. Do you have any tricks of your own or any considerations for setting a date for your travels? Let me know! I’d love to hear how other people plan their adventures!


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