Now that the year is almost over, here are some questions you should ask yourself about where you want to travel in 2026.

 

Here's why: Planning ahead will give you peace of mind and help you save a lot of money!

 

Your friends will not only start wondering if you hit the lottery because you're traveling so much, but they'll also wonder how you have the energy to do all this planning.

 

I could go on and on… But here's what you need to know right now…

• Where do you want to travel?
  • Make a spreadsheet with different options. For example, in spring, I want to go to Madrid or Athens. The goal isn't to book everything now, but when deals show up, you can decide quickly where you want to go.
  • Don't forget: Be sure to travel during shoulder season, where you can have the best prices and best experience. For those who like traveling to Europe, that's in the spring and fall.
• What type of trips do you want to go on?
  • For example, do you want to do outdoor camping or explore a city? Figuring out this type of stuff will also help you assess whether you have the right equipment, and there are still end-of-year sales to be had.

 

• How many times do you want to travel?
  • Plan both the big trips and the light trips. The big trips are 5+ days and require extensive planning, while the lighter trips are more weekend-friendly and may involve domestic travel or a road trip.
• Who do you want to travel with?
  • Seriously, who you travel with can make or break your trip. Think about who would bring you joy on the road, but it's more than that. I like to use a mental trick: Who would bail you out of jail and make you laugh at the same time? 
  • Or are you ready to try solo travel in 2026?

 

• When do you want to travel?
  • Which holidays do you want to combine with your time off to maximize your days away? I made a calendar last year showing the best times to take off, and I might make one for this year too.
  • Booking travel is like Goldilocks—there's just the right time. You don't want to book too soon or too late, or you'll pay a lot more. For international flights, the sweet spot is 2 to 8 months before departure, and for domestic flights, it's 1 to 3 months.
• How are you going to pay for it?
  • Figure out which credit cards you want to get this year to earn the most points. Also, check the credit cards you already have to make sure you're using them in the best way possible.
  • I currently see tons of deals on Going.com, so start booking them now to capture your savings.
• Did you take care of the boring stuff?
  • Check to make sure your passport is still valid. If your passport expires this year, renew it first because many countries won't let you visit if your passport is expiring in 6 months.
  • Find a travel insurance provider. If you don't already have one, start doing some research so when it's time to travel, everything is automatic. As you know, I use Safety Wing .

 

One thing to note is to be flexible. Not leaving room for life will make you miserable, and you might miss some major life events, so don't plan things too much.

 

In short, a little planning now will make traveling much easier for the rest of the year.

 

Give it a try and let me know how it turns out.

 

Keep traveling,

Andrew