Skip to main content

Travel tips and tricks: 5 dumb mistakes I make every time (but you can avoid)

Travel tips: Do as I say, not as I do. Please.

I’ve reached an unusual anniversary in 2022. This marks 10 solid years that I’ve been traveling constantly. Over the course of that decade on the road, I’ve been to all corners of the world, resided almost exclusively out of Airbnbs and hotels, and—for the most part — lived entirely out of a bag or two nearly every step of the way. The only occasions that involved traveling with more bags were the months of road-tripping, and living out of a car or van isn’t exactly far off from minimalism.

With all that travel experience, you’d think that by now I’d have the entire process streamlined to perfection. But while my travels are certainly less stressful than they used to be, there are a few mistakes that I tend to make again and again—maybe not as frequently as I used to, but they still happen. To that end, here are a few travel tips to keep in mind that will help you avoid these all-too-common mistakes.

Related Videos
Tall stacks of suitcases.

Packing too much stuff

For a while there, I had my luggage situation trimmed down to a single, light bag that I could (and did) live out of for months on end. Eventually, I started missing little luxuries and conveniences. It started with my guitar, which I began lugging around in a heavy case. Then I wanted a power strip for plugging in all my devices. Then some paper books, because sometimes you want a real book rather than a Kindle, right? Things spiraled out of hand; just the other day, I ended up putting my guitar and a suitcase full of crap into a friend’s storage near Amsterdam. I’ll pick it all up when I’m passing back through . . . eventually.

Arguably my top piece of advice to travelers involves packing less stuff. You might think you need a different outfit for each day, but you don’t. I’ve spent a lot of time around travelers, and they almost always wear the same handful of clothing items even if they have a lot more. Forget all the “just in case” junk. Leave toiletries at home and buy them once you arrive. Load up the Kindle. In other words, do anything you can to trim the excess.

An airbnb in the woods.

Picking a “cool” Airbnb without checking the location

It happens all the time: I pick an Airbnb that offers an amazing space —light and spacious, cool balcony or pool, hip décor, maybe a great view — then arrive to find that it’s in an entirely impractical location. Maybe it’s difficult to reach from the airport, or once checked in, it’s far away from everything worth seeing. Or maybe there aren’t any places nearby to get food or do laundry. Whatever the case, the place looks great, but the location sucks.

Take the time to do some research on the neighborhood you might be staying in. Check Google Maps for any businesses you deem essential — a grocery store, gym, or whatnot. Make sure that it’s near or at least accessible to the sites you want to visit. It’s also a good idea to use Google Street View to take a look around and see if you like the vibe.

At the airport.

Forgetting to ask for the upgrade

Over the course of a particularly busy year, I can take upwards of twenty separate flights. I’ve found that when I ask about upgrades at the gate, I end up getting them as often as every second or third flight — when I remember to ask, that is. Somehow, I consistently manage to forget.

These upgrades can transform your flight experience. Sometimes it means an entirely free bump up to first class, while sometimes I end up having to pay $50 or so — totally worth it for an eight-hour flight. Frequently, if no upgrades are available, they’ll check the seating chart to see if there’s an empty row I can have to myself. In any case, it never hurts to ask.

Athens when empty.

Neglecting to check the calendar

I tend to plan my itinerary around what makes the most sense for me personally, without considering what’s going on at a particular destination during the date in question. For example, I once booked two weeks in Athens because it made sense on my way from Italy to Turkey, but when I arrived, I found that the city was empty and everything was closed due to a two-week-long holiday.

Before scheduling flights and accommodations, be sure to check that there isn’t anything conflicting with your plans. That could mean holidays, a low season (if you’re looking to party), a high season (if you’re looking for quiet), a rainy season, or a hot season. I screwed up once and brought my easily-overheated mother, aunt, and uncle to Naples in August. If I have any advice for traveling, it’s this: Trust me, you don’t want to make the same mistake.

The cabin of a plane.

Picking the front of the plane

It might seem intuitive to select a seat as close to the front of the plane as possible, especially if you’re attempting to go carry-on-only. It allows you to get off the plane faster, right? But it also means that you’ll often board last, which can translate into problems with finding overhead storage for your carry-on. Suddenly you’re forced to have it checked into the belly of the plane, and your front-row fast escape has just turned into a long wait at the baggage claim.

Avoid the first dozen rows and aim for someplace in the middle of the plane. It’s not going to delay your disembarking by much, but it will ensure that you find a place to stow your bag.

Editors' Recommendations

7 really, really cold places you need to travel to in 2023
When a typical tropical vacation just won't do, take a trip to the world's most extreme cold-weather destinations
Magdalenafjord Svalbard Islands Norway

For most of us, the "perfect" vacation involves sipping neon daiquiris on a white sand beach overlooking impossibly blue ocean waters. But, for others, it's all about experiencing something new and unlike anything they've done before. They're looking for a legit adventure to a part of the world where few "normal" travelers dare to go. We're talking about visiting some of the coldest places on earth.

We're well into winter here in the northern hemisphere, which may not seem the ideal time to travel to the coldest places in the world. But, it is arguably the best time to experience the real side of truly cold-weather destinations or to start planning your next cold-weather trip. Here are seven really, really cold places worth visiting in 2023.
The Svalbard Islands, Norway

Read more
I tried nearly all the ski lodges in Whistler and Banff: Where you should stay
The best Whistler and Banff hotels for every type of adventure

With its epic mountain landscapes, the Canadian Rockies and western coastal region offer some of the most renowned outdoor opportunities in the world, whether you’re into snow sports, mountain biking, or simply enjoying magnificent scenery. The Banff and Whistler areas in particular are popular thanks to their combination of natural splendor and charming mountain hamlet vibes. With dozens of hotels to choose from, which one is right for you? Here, we’ll check out the top Banff and Whistler ski resorts and hotels for a variety of trip categories: Budget, family-friendly, and so on.

You can rely on these recommendations, as I have vetted each and every one of them personally. Last summer I spent three solid months crisscrossing the region, and along the way I stayed at nearly two dozen lodges. Not all of them are worth planning your outdoor adventure around, but here are several that will provide a superior experience.

Read more
The 2023 travel trends to know before you plan your vacation
From remote work to van life, this is how we'll travel in the new year
A man traveling with a suitcase that's filled with the best travel gear because he read this list.

After two years of little to no international travel due to border closures and other Covid-related restrictions, last year brought globetrotting roaring back — so much so that many airports struggled to cope with the surge. Similarly, in 2023, travel will continue to grow toward pre-pandemic levels as even more people become comfortable looking abroad, so now seems like a good time to dive into the big 2023 travel trends to come.

The way people travel is changing, not only in regards to how they do it but why they travel as well. This is having a major impact on the realm of travel in general. So without further ado, let’s peer into the crystal ball and take a look at the not-so-distant future and the travel trends we expect to see in the new year.

Read more