The Most Common Mistakes When Planning Travel (and how to avoid them!)

It’s been a minute since we all traveled “normally,” right? And I’m pretty sure we all need a vacation by now! I’m currently trying to plan a few possible trips for the future, and I’ve found myself feeling the same anxiety about wanting to do it “right.” These are the same things I felt and thought in my early days of travel!

So, I challenged myself to come up with the most common travel mistakes I’ve made (and I know others make, too). And of course, I’m not the kind of person who can come up with a problem but no solution. Here’s my list of common travel mistakes and how to avoid them in your future travel planning!

Booking a Hotel Far, Far Away

Sometimes it’s an effort to save money, sometimes it’s because it looked a lot closer on the map, and sometimes you booked the hotel before you realized where all the things you wanted to do were located. Whatever the reason, it’s happened to us all! Here are some tips for making sure you book the best hotel for you!

Trying to Save Money

It’s almost always worth it to stay in a central location. It’s pricier for a reason, maybe more than one reason! When thinking about hotels and your budget, make sure you check public transportation costs, traffic, time to get from where you’re staying to where you want to be. You might just change your mind about that “cheap” place 20 miles away when you find out it will take you an hour to drive that distance, or run you $6.50 per person, each way, using public transit!

Avoid this: Run the numbers before you book!

It Looked a Lot Closer on the Map

I’m totally guilty of this. I look at where it is on the map, and I think, “Oh, sure! That’s close enough! We don’t mind walking!” And then we get there, and the mile-and-a-half walk one-way gets old after that first round-trip. Whoops!

Avoid this: Map it to find the actual distance!

You Booked Before You Realized Where Everything was Located

Whoops! I’ve totally done this before. If you’re going somewhere you’ve never been, you don’t know the proximity of things. For instance, if you’re staying in D.C., you may not realize that the Tacoma Park Neighborhood is in D.C., but far from the National Mall, Monuments, museums, and basically everything everyone wants to do in D.C. Once you actually see it on a map, though, you realize that somewhere closer would be better.

Avoid this: Use Trip Advisor or a mapping app to save all the things you want to do, and then decide where you should stay based on that.

Hotel or vacation rental? Or maybe bed a breakfast? Check out my guides to figuring out where to stay on my Accommodations Page!

Assuming There will Be Parking, and It Will Be Free

Having lived in D.C. for 13 years now, I never expect parking to be free–not anywhere, not any time, not for any reason! But this is one of the most common complaints I hear: they didn’t expect to have to pay for parking. And they thought there would be plenty of it to go around!

Avoid this: Call or e-mail your hotel to ask about the cost of parking, both at their property and around the area. Then decide whether or not driving or getting a rental car is a good idea, or maybe walking is better!

Also helpful: My Top 10 Travel Hacks (after 15 years of blogging!)

Not Wearing Practical Shoes

I know, I know. I’m a total fashion kill-joy! But seriously, your feet will not thank you for putting fashion above their well-being. Bring a change of shoes with you in your purse if you want to, but if you’ll be walking miles and miles, traversing cobblestone streets, or hiking (especially hiking!), please do your feet a favor and bring responsible shoes. Having been through two corrective foot surgeries, I can tell you how important this is!

Avoid this: “Responsible” shoes can be sneakers, supportive sandals, water shoes, etc. Think about what you’ll be doing as you plan your trip, and pack accordingly!

Don’t take my word for it! Check out this post I did in collaboration with my podiatrist: The Ultimate Guide to Your Feet and Your Travels

Not Making Reservations When Necessary

There’s almost nothing more disappointing than getting to a restaurant, tour, show, etc., and realizing you can’t get in because you don’t have a reservation. Why is it so disappointing? Because it’s so preventable! I have definitely been left kicking myself for missing out on something I really wanted to do.

Avoid this: Do a little Googling! If there’s a special restaurant, experience, or event you don’t want to miss, Google, “Do I need reservations for _____.” If you do, someone will let you know in a blog post, online review, or the company themselves!

Definitely need reservations for this. It’s one of my most-view blog posts ever for a reason: Dining at Mama’s Fish House on Maui

Planning Every Second of the Trip

There’s a saying from Solomon, the wisest man to have ever lived: “Avoid all extremes.” Just as you can accidentally let things fall through the cracks without planning, you can also ruin your own fun trip by making too many plans! Strike a balance and plan one to three activities for each day. This will give you time to explore a little, enjoy the moment, think about where you are instead of where your next stop is supposed to be.

Also, allow your plans to change. You might just stumble upon something better than you could have planned!

Avoid this: If you must have a schedule, make sure to also schedule down time! This could be a designated beach day, a free morning to simply roam the streets of a new city, or making no plans for your last day as a “catch all” for the things you didn’t have time for during the rest of the trip.

My tried and true method: The Ultimate Guide for How to Plan a Trip

Buying Plane Tickets from a Third Party

Third party websites like Skyscanner, Kayak, CheapO Air, Orbits, Expedia, etc., are wonderful tools. I use them myself! But when it comes time to actually purchase an flight itinerary, I always, 100% of the time, book directly with the airline. Why does this matter? It’s like built-in insurance.

You Will Not Pay More

There’s a terrible myth going around that third party sites provide deals. This is not true! Third party sites find existing deals for you. This is what makes them a great tool to use. The third party site is not giving you a discount; they simply found the best deals with one search instead of you having to search multiple airline sites to find it yourself.

You will not pay more by booking directly with the airline! You’ll just save yourself time using a third party site to find the deal you want.

You Will Not Get the Run-around

Unexpected things happen. People make mistakes when booking (I once booked the wrong date for a flight). Natural disasters occur (hello, Hurricane Harvey 2017, which shut down the Houston airport when Steve and I were trying to come home from Easter Island). Pandemics shut down travel for over a year (hello, COVID-19). If you booked with a third party, they’ll tell you to go to the airline to fix it. The airline will then tell you the third party has to fix it. This is not a rare scenario; this is how it works.

If you book with the airline directly, you will not get the run-around!

You Will Get Where You’re Going

An airline won’t leave you stranded. A third party will. Again, you’ll be getting the third party run-around while those who booked with the airline are getting re-booked.

Get where you’re going faster and book directly with the airline!

Avoid this: Find your deal using your preferred third party flight finder, but then actually buy your ticket from the airline!

More here: How to Find Cheap Flights

Thinking Everyone Has to Spend Every Moment Together

This is a recipe for disaster, ruined friendships, family feuds, wasted money, and an all-around bad time! For example, if someone really doesn’t want to go zip lining, chances are high that they’ll make everyone else wish they hadn’t come, or everyone will spend the whole time comforting them in their fear of heights. Whoever paid for that will also have wasted money because that person didn’t enjoy it. The same could be said of any experience!

Similarly, there will likely be one people pleaser on your trip who doesn’t get to do anything they want because they’re doing everything everyone else wants! So don’t get stuck thinking your whole group has to do everything together. Sometimes it’s better to go your separate ways, and then come back together for dinner to talk about your experiences!

Avoid this: Make sure everyone gets to do at least one thing they really, really want to do, even if that means dividing to conquer!

Read on: How to Plan Travel with a Group

Refusing to Be Flexible (or just not thinking about it)

It costs nothing to be flexible. In fact, it might just save you money! Shifting your trip by a day or two could save you hundreds of dollars in airline tickets alone. Instead of having a set itinerary in mind, try changing things up. It costs nothing to search different days, different hotels, different ideas.

So, be willing to move your trip by a day or two, take a longer layover, or even fly into a different airport. Keep an open mind, and think outside the box. A little flexibility could take you a long way!

Avoid this: Go into your travel planning with flexibility in mind. If you have absolutely set ideas, don’t complain if you end up paying more for the convenience!

More on this here: 5 Habits of Flexible Travelers

Are you planning travels this year? Comment below!

Need more? I’ve got all the resources you need on my dedicated Travel Planning Page!

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