amateur travel planning mistakes

These Amateur Travel Planning Mistakes Are Costing You BIG Money


I’d bet $20 you’re guilty AF of at least one of these mistakes.

posted November 10, 2024

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If you've ever planned a trip before, you know there's a lot that goes into it. You need to figure out things like dates and flights, hotels, car rentals, Ubers, excursion, etc. – it can be a lot! However, when it comes to travel planning, the amateur travel planning mistakes I'm going over in this post may be costing you some big money.

So if you're looking for some ways to not overspend when planning your next trip, this one's for you. Because in this post, we're looking at some of the amateur travel planning mistakes I see people make that's making their trips way more expensive than they need to be. 

And who wants to overpay??? No one.

This post is all about amateur travel planning mistakes that cost big money.

Mistake #1: Date inflexibility.

Having rigid travel dates is the #1 mistake costing you big money.

As a general rule, traveling on weekends is always far more expensive than traveling during the week. For instance, I've seen some hotels literally double in price when comparing their nightly rates on a Saturday compared to, say, a Tuesday.

You can typically travel much more inexpensively if you shift your dates a tiny bit. While date flexibility isn't always possible, I always recommend playing with dates when booking rooms and flights whenever you can. It's just a super easy way to save yourself sometimes hundreds of dollars, depending on the length of your trip.

Mistake #2: Booking travel arrangements at the last second.

Booking any travel arrangement at the last second is a surefire way to pay higher prices.

It's basic supply and demand. When supply goes down, but demand is high, prices go up. However, when supply is high, but demand is low, prices often drop. So when you wait to book arrangements at the last second, you're in essence trying to book when supply is at its lowest – meaning prices are at their highest.

Therefore, you should always book your arrangements sooner rather than later. You'll find cheaper prices for two main reasons:

  1. When there's less demand and greater supply, prices are lower. After all, these travel providers want to make sure they sell their inventory, because they lose money every time a seat, a car, a hotel room, etc. goes unreserved.
  2. You'll simply have more to choose from, so you aren't forced to go with a more expensive option because that's all that's still available.

Mistake #3: Traveling during seasonal peaks.

When you travel during a peak season, you're going to pay a lot more.

Again, it goes back to supply and demand. During peak seasons, there's a lot more interest in travel, and therefore, a lot more demand. So travel providers know they can sell their supply without much problem. But when you travel during the off-season, there's often way more supply than there is demand, so these companies know that selling out is quite unlikely. To counteract this, they drop prices in order to book as many reservations as they can.

For that reason, I always recommend traveling during the off-season when you can. But if that's not possible, traveling immediately before/after a major holiday weekend is a good alternative. For instance, some of the cheapest beach trips I've ever seen fell directly before and after Labor Day weekend.

Mistake #4: Not using free loyalty programs to earn rewards.

This one more so applies to frequent travelers or people who have their go-to travel providers. Nonetheless, a lot of people spend more money on trips than they need to simply because they don't take advantage of free loyalty programs offered by travel providers.

These programs allow travelers to, in essence, log their trips and money spent on reservations to their loyalty accounts. And the more money users spend on reservations with that provider, the more "points" they earn, which can be traded in later on for rewards. These include things such as free or discounted flights, seat upgrades, hotel stays, car rentals, etc.

Additionally, travel providers often have partnerships with other non-travel brands, through which points can also be earned. For example, Delta and Starbucks have a partnership, in which members of Delta's free-to-join SkyMiles program can earn travel rewards when buying Starbucks, as long as their Delta and Starbucks memberships are linked.

Now, I'm in no way, shape, or form guaranteeing you'll ever earn enough rewards through these free programs to get an entire trip for free. But every penny saved is a penny back in your pocket – and another penny to spend once you actually reach your destination.

So if you have a favorite airline, cruise line, rental car provider, etc., and you aren't a member of their loyalty program, I want you to go to their website after reading this and sign up. You may even be able to retroactively apply recent reservations to your new membership. That way, you can start earning those rewards as soon as you register!

John Denn

Your New Internet GBF

On this blog, we chat about all the things related to everyday life in your thirties. From crafting the perfect first Tinder message, to bitching about the price of groceries, to sharing some brutal truths you probably need to hear, we're in this together – and I've got your back, bestie.

John Denn

Your New Internet GBF

On this blog, we chat about all the things related to everyday life in your thirties. From crafting the perfect first Tinder message, to bitching about the price of groceries, to sharing some brutal truths you probably need to hear, we're in this together – and I've got your back, bestie.

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