Travel Tips and Tricks: 5 Stupid Mistakes I Make Every Time (But You Can Avoid)

I have reached an unusual birthday in 2022. This marks 10 solid years of constantly traveling. In this decade on the road, I’ve been to every corner of the world, resided almost exclusively off of Airbnbs and hotels, and for the most part lived entirely with a bag or two to almost every step of the way. The only occasions that involved traveling with more bags were the road trip months, and living in a car or van isn’t exactly far from minimal.

With all this travel experience, you would think I would now have the whole process streamlined to perfection. But while my travels are certainly less stressful than before, there are a few mistakes I tend to make again and again – maybe not as often as before, but they still happen. To that end, here are some travel tips to keep in mind that will help you avoid these all-too-common mistakes.

packing too much stuff

For a while there, I had my luggage situation reduced to a single lightweight bag that I could (and did) live with for months. Eventually, I started to miss the little luxuries and conveniences. It started with my guitar, which I started lugging around in a heavy case. Next, I wanted a power strip to plug in all my devices. Next, paper books, because sometimes you want a real book rather than a Kindle, right? Things got out of control; the other day I ended up putting my guitar and a suitcase full of shit in a friend’s depot near Amsterdam. I will pick up while ironing. . . ultimately.

Probably my best advice to travelers is to pack less stuff. You might think you need a different outfit for every day, but that’s not the case. I’ve spent a lot of time with Travelers, and they almost always wear the same handful of clothes even though they have way more. Forget all the “just in case” garbage. Leave the toiletries at home and buy them once there. Charge the Kindle. In other words, do whatever you can to trim the excess.

An airbnb in the woods.

Choosing a “cool” Airbnb without checking the location

It happens all the time: I choose an Airbnb that offers amazing space – bright and spacious, cool balcony or pool, trendy decor, maybe a great view – then I arrive to find it’s in a totally impracticable. Maybe it’s hard to get to from the airport, or once checked in, it’s far from anything worth seeing. Or maybe there are no nearby places to eat or do laundry. Anyway, the place looks great, but the location sucks.

Take the time to research the neighborhood you might be staying in. Check Google Maps for any businesses you deem essential — a grocery store, gym, or whatever. Make sure it’s close 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 request the upgrade

During a particularly busy year, I can make more than 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, which is when I remember to ask. Somehow I always manage to forget.

These upgrades can transform your flight experience. Sometimes that means a completely free ride to first class, while sometimes I have to pay around $50 – well worth it for an eight hour flight. Often if no upgrades are available they will check the seating chart to see if there is an empty row I can have for me. Anyway, it never hurts to ask.

Athens empty.

Neglecting to check the calendar

I tend to plan my itinerary around what makes the most sense to me personally, regardless of what’s happening at a particular destination on the date in question. For example, I once booked two weeks in Athens because it made sense on the 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 vacation.

Before scheduling flights and accommodation, be sure to check that there is nothing conflicting with your plans. This could mean holidays, low season (if you’re looking to party), high season (if you’re looking for quiet), rainy season, or hot season. I messed up once and brought my easily overheated mom, aunt and uncle to Naples in August. If I have one travel tip, it’s this: Trust me, you don’t want to make the same mistake.

The cabin of an airplane.

Choose 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 trying to travel with only hand luggage. It gets you off the plane faster, doesn’t it? But it also means you’ll be boarding often last, which can result in problems finding top storage space for your hand luggage. Suddenly, you’re forced to have it checked into the belly of the plane, and your quick escape to the front row has just turned into a long wait at baggage claim.

Avoid the first twelve rows and aim for somewhere in the middle of the plane. It won’t delay your disembarkation much, but it will ensure you find a place to store your bag.

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