Timing is Everything: When is the Best Time to Travel

Deciding when to travel can be just as important as deciding where to go. The time of year you choose for your next vacation can have a big impact on your experience – from crowds and costs to weather and availability.  I’m here to break down the pros and cons of traveling during different seasons to help you plan your trip for optimal enjoyment.

Tips for Planning

  • Research Average Temperatures: Use Google to check the average temperatures and weather conditions for your desired locations.
  • Consider Your Availability: When can you take time off?
  • Seasonal Considerations: What season will it be when you plan to travel?
  • Trip Type: What kind of trip are you planning?
  • Holidays: Are there any major holidays at your travel destination during your planned visit?

Scheduling Your Trip

Do you have time off and now get to decide where to travel? This is the most common scenario, but you may also have a destination in mind (maybe one from your bucket list) and need to determine when to take the trip. Deciding when the best time is to travel begins with when you can travel, then look at these other factors to figure out the best time to go or where to travel when you have time off.

Seasonal Considerations

Have you ever had a location in mind, gotten the time off and started planning only to realize you hadn’t considered what season it is where you’re going? This has happened to me, and I learned to check the seasons first, before planning anything else.

Remember that the north and south hemispheres have opposite seasons. One year I was in the United States for a conference when the clocks sprung forward, and two weeks later I was on vacation in Australia when the clocks fell back. It was bizarre going from the excitement of spring to the sadness of fall with a lot of talk about coping with winter.

If you are from a place with extreme weather (like me in Northern Canada) you could end up with a massive discrepancy in temperature when you travel to the southern hemisphere for Christmas or in January. There is nothing wrong with this, but it is a consideration. For international trips, check the seasons.

Weather

Spring, summer, fall and winter are also accompanied by other seasons, such as, rainy, hurricane, and wildfire. These seasons can have huge negative impact on a trip, with the possibility of the trip not happening at all. I have friends who spent their honeymoon in the Caribbean helping fill and place sandbags and then have no power and flooding because they were there during hurricane season.

Rainy Season: It might not be catastrophic, but it can disrupt plans. For instance, in Thailand, the rainy season meant only one day of torrential downpours during my trip.

Hurricane and Wildfire Seasons: These are highly unpredictable and can ruin a trip. If you’re adventurous, enjoy saving money, and can be flexible, it might be worth the risk. Ensure you book flights and hotels that can be canceled last minute.

Heavy rain falling with a group of people walking by.
Disneyworld downpour in July.

Trip Type

What type of traveller are you, or what type of experience are you seeking with this trip? The best time to travel may be based on what you’re looking for. The timing of a trip may be dictated by the goal of experiencing an event or an activity. A few years ago, we had an amazing trip to Japan, but we were disappointed when we found out we weren’t going to be there at the right time to see sumo wrestling. In addition to sports, there are other activities, such as whale watching, that have a season.

Other trips that are impacted by timing are popular locations, theme parks, and outdoor adventures. This is another case where crowds and weather can reduce the experience, but you can still go. We have been in Disneyland and Disney World on July 4th. Just be realistic with your expectations.

Pathway through a bamboo forest.
Bamboo forest in Osaka, Japan, in August.

Holiday Considerations

Like the seasons, we are familiar with the major holidays where we live. When planning a trip, check the places you’re considering going to see if there are any major holidays when you will be travelling. This is another thing to be aware of so you can plan around it, or you may be able to capitalize on the holiday and have a great experience. Holidays in other countries may result in places you want to visit being closed, large crowds, or a ban on alcohol consumption.

When I would consider planning a trip for Florida, Hawaii, Fiji, London and Thailand. I chose some geographically dispersed places to give you an idea of when it is a good time to travel to these areas.

Florida

The home of the Eastern Canadian snowbirds. Florida is where a lot of Canadians choose to spend winter because of the weather. I have been to Florida several times and it is always a busy trip full of theme parks, beaches, and one of my favourite activities ever – swimming with manatees. One place in Florida made my list of best places to travel in the United States.

Florida is tropical, which means hot and humid with a hurricane season. June through August can be unbearably hot and humid, and June through November is peak hurricane season. November through April is the best time to visit Florida.

I have been to Florida in July, August, and September and only ever dealt with the heat and humidity, and bouts of heavy rain. It is high season for the theme parks because school is out so the best time to go is in the spring.

Hawaii

The best time to go to Hawaii is in the winter if you want to see the big waves and potentially a surf competition. This is on my bucket list. The downside is from the latter half of December to February is the busiest time of the year, so you will be there during high season.

If you want to see some amazing sites and enjoy snorkelling, Hawaii has great weather year-round.

If you’d like to go whale watching, then you want to go from November through April. This is also rainy season, but the rain does not last long there. 

Single palm tree in front of the ocean with a setting sun.
Maui sunset in March.

Fiji

After reading about a great deal on flights to Fiji, I quickly searched the weather to make sure the flights weren’t cheap because it was typhoon season or something. It turned out, it was the best time of the year to go, between May and October. This may seem counterintuitive because that is winter in Fiji, but there winter means still hot but less rain and humidity.

For those of us in the northern hemisphere that do have actual snow and cold in the winter, it is not ideal because the best time to visit Fiji is during our summer. June to September is high season, so it may be worth checking out in April or early May as a prelude to summer. I highly recommend Fiji; it is an incredible country to visit.

Palm trees, ocean and islands with a setting sun.
Mana Island – Fiji, in August.

 London

This is one I can speak from experience, as I lived there for a few years and have visited several times. Winter in England is wet and cold. If you want to avoid the crowds and own a few good layers and raincoat, consider London in the winter. There are so many museums and indoor activities to experience when the weather is bad.

If you want to increase your chances of better weather to enjoy time outside, go in the summer but it is very busy. The optimal time for London is the shoulder seasons.

White stone building with columns, at night.
St. Paul’s Cathedral, London, in November.

Thailand

In addition to missing sumo wrestling in Japan, we also ended up in Bangkok during monsoon season in Thailand, on the same trip. Between July and October is rainy season. It gets worse each month so July shouldn’t be too bad, but you may want to avoid September and October.

We were there in August, and it was not bad at all. There was only one day of heavy rain, but it was very hot and humid.

November through March are the best months weather wise. Christmas will be high season prices. March to May are the best times to visit Thailand.

Where to Travel at Different Times of the Year

Where would I plan a trip in the following scenarios.

An escape from winter in January

This is a common one everyone who lives in a cold climate. If I wanted an active trip with nice weather and beaches, Costa Rica would be my first choice. If I wanted a cheaper week on the beach, I’d consider an all-inclusive holiday in Mexico. We had a nice trip to Huatulco last year in the winter.

Beach with ocean waves.
Beach time in Huatulco, Mexico, in December.

A summer vacation to explore

Summer vacation is a challenge because it’s high season. We really enjoy a road trip because we can see several places.

I would like to do an Alaskan Cruise one year and this is something that is only available in the summer. If you’ve never been on a cruise, this article covers our first experience. We may forgo the cruise and do a road trip to Alaska so we can bring our dog, but that will be a longer trip.

Another option is the Ireland and/or the United Kingdom. It is expensive and London is very busy, but the weather is better and there are lots of places to explore outside of London.

River flowing with hills on both sides.
Queen’s View, Scotland.

An off-season big trip

For those of us no longer tied to school schedules, October and November are the best time for off-season travel. Spring is also a shoulder season for travel but spring breaks often drive up the prices and crowds.

This would be a great time to go back to Japan and explore more of the country. I would consider going in November to be able to watch a sumo tournament.   

This is also a good time to go to Europe. I have not been yet, but I would consider a trip to Italy and Greece around this time of the year.

The last option would be a Disney trip. Off-season is definitely a more enjoyable experience. I would love to see Disneyland decorated for Halloween. If you love Christmas decorations and lights, I highly recommend taking in the Disney magic.

Castle lit up with christmas lights.
Disneyland Castle decked out for Christmas.

Conclusion

This may seem like common sense, but I learned some of these lessons the hard way. I hope by sharing these tips, I can save you from a disappointing trip. If there is somewhere you really want to go or something you want to do, do a bit of research so you know what to expect before you book the trip.

Weather and natural disasters are never predictable so there is always an element of risk involved. Travelling has taught me to relax and be flexible because so many things are out of your control. Mitigate as much risk as possible and then go in with an adventurous spirit.

Have you ever taken a trip and realized you booked it for the wrong time? Share your experience in the comments.

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