KISS Theory of Traveling

bangkok airport

The other day a reader who also works within the travel industry reached out for help with airfare advice. That’s probably one of the most common questions I get here on LandLopers, how to score cheap plane tickets and how to plan the trip itself. The problem is, as they were asking me the questions I realized that for someone in the industry, they didn’t know a lot about the process. He tried to make it a lot more complicated than it needed to be and it reminded me of why I started the web site in the first place, to help my friends through similar situations. I also realized something else, something I have written a little bit about in the past but which I never fully articulated into one statement. The real secret to travel, to finding deals and getting out there and exploring the world isn’t based on a special web site or particular skill set, it’s keeping things as simple as possible. So with that in mind, I present to you my KISS Theory of Traveling.

KISS is an acronym that means Keep It Simple Stupid. While I’m not trying to call anyone stupid, the name fits and I think is more than appropriate for my theory. Here are some ways through which my theory can be applied.

 South African Airways

1. Airfare – Airfare is very misunderstood and most people believe that if they only keep looking, they’ll find a better price out there somewhere. Well, usually they won’t. The reason for that has to do not with luck or laziness, but with how these sites run in the first place. In the U.S., online travel agencies (OTAs) like Expedia and Orbitz get most of their price information from one source, or a source that ultimately leads back to the same source. Another category of travel site is called an aggregator, Hipmunk and Kayak and two great examples. These sites scrape data from airline sites as well as OTAs to present the customer with information. So no matter how many different sites you check, you will only see slight variations in price depending on your search. This is why keeping it simple is so important.

Many of us get lost in the weeds when it comes buying airfare, the choice is overwhelming and at some point we break down and just buy something, even if it’s not the best deal. Instead, when you know you’re traveling somewhere use just a couple of web sites to see what the fares are. I always use the website of my airline of choice (US Air) and then usually Hipmunk to determine a baseline cost. Then, if time allows, I check it every week or so to determine what the prices are doing. I also set a target price and should the fare ever hit that target, then I buy immediately. There are exceptions to this of course, partnered deals and promotions for example, but on the whole just keeping the sites checked to a minimum and keeping the process simple is best. The same goes with the route itself.

Unless you’re flying for the sole sake of getting more miles (a mileage run) then ideally keeping the number of flight legs to a minimum is key. The reason for this is convenience, sanity and the likelihood of keeping your checked bags with you. Frankly, the more legs, the more chances there are of delays and other mishaps occurring.

 Dubrovnik Old Port Croatia

2. Planning – Travel is the largest industry in the world and that’s great in that we have a lot of choice when planning the next big trip. But it also results in information overload, more prevalent now than ever before. Guides, books, web sites, blogs, friends and family all come together to create a cacophonous assemblage of advice and banter that is confusing at best. That, coupled with the fervent desire most of us have to make every trip The Perfect Trip results in a pressure that creates inertia. We’re afraid to make decisions because we don’t want them to be the wrong ones. Instead of getting lost in the details, this is the perfect time to keep things simple.

The worst thing you can do on any trip is to over-plan; trying to overcomplicate the trip in an effort to make it The Perfect Trip. Contrary to initial logic though, trying to make sure you do and see everything in a new destination usually means you won’t be able to enjoy anything. One of the great mysteries of travel is when the completely unplanned and spontaneous happens; magic that can never be anticipated or duplicated. This magic is smothered when a trip is over-planned. If you don’t keep your trips simple, then you’re missing out on the great pleasure that travel gives.

 Zebra Zimbabwe

3. Doing – A few years ago I wrote a post about how there is no such thing as a Dream Trip. In that post I wrote how people invest so much in hoping and wishing to take one Dream Trip, that they forgo other ways to travel and probably never will even take that Dream Trip. If someone thinks that they can’t go on safari in South Africa unless they spend $25,000, then they’ll get lost in that erroneous fact instead of trying to find other ways to realize their dream.

Travel doesn’t have to be for the über-wealthy and famous. There are ways for everyone to travel, as long as you stay realistic and keep things simple. Set your destination and your budget and then start working towards that goal. Two years ago I stopped drinking Starbucks every day and saved more than $1,000 over a year. That money was reinvested in travel. You can save a lot of money in many different ways and that trip you’ve been pining on can be a reality sooner than you realize. Also be realistic. I know that how much I save I’ll never be able to afford a $75,000 per person private jet adventure. Instead, I plan for trips that are within reach. Just stop getting overinvested in complicated travel and instead find simpler, easier ways to travel and see the world.


Like many aspects of life, the more complicated we make things the harder they are. By being realistic and keeping things simple, not only is the travel experience richer and more enjoyable, but it’s also much more realistic.

What are some other ways keeping things simple helps in the travel process?

By: Matt Long

Matt has a true passion for travel. As someone who has a bad case of the travel bug, Matt travels the world in order to share tips on where to go, what to see and how to experience the best the world has to offer.

5 thoughts on “KISS Theory of Traveling”

  1. Great post with great points, as always Matt!

    Regarding the first point about airfare, it’s always a quagmire – will prices go up, will they go down, will the airline dump seats 1 week before departure? Our travel booking site has a nifty technology called Rate Shrinker, which literally does just that – if the price of an airline ticket you’ve booked through us goes down, we’ll rebook you on the cheaper fare and refund you the difference. No itinerary changes, no flight changes. Boom.

  2. The KISS Theory applies so appropriately to so many things in life. In the past I have always wanted to make each trip the “Perfect Trip.” That was until my fiance and I went to Greece with no plans but to attend a wedding. We stayed with a local family friend and lived like Greeks for the week preceeding the wedding. It was such a blast. We ended up seeing most of the important sights in Athens, but we never felt like we were missing anything because we really had no set standards on everything we needed to see. Plus, not seeing everything gives us an opportunity to go back and explore more!

  3. Really, the KISS theory is great!

    We start up this summer from Como (ITA) to Shkoder (ALB) traveling with the car thrue Slovenia, Croatia, Bosnia e Hecegovina & Montenegro. Was 21hours long but it was enjoyable and realistic. The return was from Durres (ALB) with ferry to Bari (ITA) and then until Como, northern Italy.
    Sometimes, searching and trying can find more ways to visit, travel and to see other countries.
    I think to apply the same to next summer for other places.

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