Hitchhiking The Skies – Flying With Travis And His Family

Filed Under: Advice, Great Deals

Travis is my first new contributor to the blog, who will be writing a post every Wednesday to start. The idea behind adding guest contributors is to add different perspectives to the blog. Travis has a unique approach towards travel, given that he travels almost exclusively with his wife and young children, which is in stark contrast to my travels, which are usually alone.

Travis is currently on a month-long trip to Southeast Asia with his family:

The universal symbol for those looking to hitch a ride is to stand by the side of the road with arm extended away from the body and thumb pointed up, tilted in the direction you are trying to go. The hope then is that a passing driver going in your direction will stop and offer you a ride. Of course, this applies to those hitchhikers who have a specific destination in mind.

My Dad tells of a guy he met once who just wanted to explore the country. Didn’t care where he went, just wanted to go. He would stand by the side of the road with one thumb pointed in each direction and jump in the first car that stopped, regardless of which way they were headed.

Whichever plane is leaving first!
Travis hitch-hiking at the airport!

This more or less describes my family’s travel philosophy – we don’t really care much where we go, we just want to go. The modern equivalent of standing by the side of the road with a thumb pointed in each direction is to watch various websites such as the FlyerTalk Mileage Run Forum or the The Flight Deal and wait for a fare war, mistake fare, or otherwise really good deal that you can jump on. The general idea of these websites is to post fares which are cheap enough that people can and do fly them just for the miles (or status), so if you actually ascribe some value to visiting the destination, then it’s probably a good deal.

We fly where the market takes us. Several years ago, Spain, Turkey, and Ireland were significantly cheaper than the rest of Europe. That year we did all of those. Then competition in the Middle East heated up – so we went to Bahrain. Recently the rise of low cost carriers serving Scandinavia has made that part of the world a cheap destination to get to (though not necessarily to be in!), so we went to Norway and Sweden and have an upcoming trip planned to Denmark.

My wife and I are often asked by friends and family for help booking travel. They hear about all the cool places we go, and how often we travel, and figure that we must have some secret for getting great deals on airfare because they know we’re just an average middle class family. So they come to us and tell us that they want to take the kids to Orlando over spring break, leaving Saturday and coming back the following Sunday. And all they see are $600 tickets. Can we help?

Of course we take the obligatory look at ITA Matrix and confirm that, sure enough, it’s expensive to get to Florida (or anywhere else) around Spring Break. Yes, it’s going to cost the same amount for a ticket to Florida as we spent to go to Norway. Then if they are still listening, we get into our Rules of Travel Deals.

  1. You can get a deal to anywhere you want if you don’t care when.
  2. You can get a deal anytime you want if you don’t care where.

If you have sufficient flexibility, travel can be really cheap. I’m not even talking about using miles and points at the moment, just being opportunistic when good revenue fares exist.

For example, just this year WOW air started selling tickets to Iceland from the East Coast for $200-$300. The Middle East is still cheap with Doha at $650 from various parts of the country. And SE Asia can be accessed via Jakarta or Bali for $650, again from a variety of cities. Sure, you need to have some date flexibility, but the deals are there.

In many cases, it is possible to get a ticket to an exotic destination for just a bit more than it costs to fly across country! You just have to do be willing to go when the masses want to stay home. Or go where the masses aren’t going.

But make no mistake, if you want to go to a specific place on a specific date, the airlines have you over a barrel. And they know it.

This all leads to the story of how we constructed our current trip to Southeast Asia. This trip had the potential to violate our Rules of Travel Deals – we were constrained to be in Penang for the wedding of one of my best friends. Worse yet, that date was a few days before Christmas, at the height of the US travel season. Fares had the potential to be ugly.

Fortunately, we knew the wedding date a year in advance. We discussed our options and what we might need to do to save money. Then like a hunter stalking his prey, we sat back and waited.

Sure enough, within a few months a mini fare war broke out to Indonesia. United started offering fares in the $800’s from much of the mid-continent. American did likewise. Eventually Delta even threw Bali into the mix at the unbelievable price of around $600 (since matched by United out of Houston or Newark.)

It met our budget. We pulled the trigger to Jakarta. Even with the Visa-on-Arrival fee ($35 per person) and departure tax (~$13), it was still too good a deal for us to pass up.  Saving $300 or so per ticket is significant when you are traveling as a family of 4.  Outbound travel needed to commence by early December to avoid the peak holiday period, so we booked the outbound on the last day allowed by the fare rules. Then we put the return very early in the new year, thus giving us right around a month in Southeast Asia.

This was back in May, and the trip wasn’t until December. Would a better deal come along? That’s always a risk, but a risk we frequently take. A bird in the hand is worth two in the bush. Find a deal you like, jump on it, and don’t look back. Or if you do look back, do it for educational purposes only – you can’t beat yourself up over it!

Once we had the tickets to Jakarta, our trip was blocked in. We knew when we’d leave, when we’d get back, and when we needed to be in Penang. We had no clue what the rest would look like.

Our default plan was to rent an apartment in Penang for a month and live like expats. We would focus less on sightseeing and more on just the living experience.  I would be able to work my day job a good amount of time. My wife and kids might meet some locals or expats to hang out and play with. It all seemed like a pretty good default, and there was no rush to make concrete plans, so we did what we always do—sat back and waited for deals……

To be continued.

  1. Travis great post! This is what we do too! I call it being an opportunistic traveler. As I tell everyone, the key is flexibility. Like you, we wait for the really good fare sales to come about. Last year, it was Italy for $250. Next year, Egypt for $350. A few years ago, London for $300, Rome and Amsterdam for $290, SE Asia for $400, Anchorage for $300, Denver for $99. In the past, we’ve gone to Europe in the winter or shoulder seasons because it’s much, much cheaper than in the summer. We pay the most to travel when we HAVE to be somewhere on a particular day or time.

  2. As a father with a young family, I am loving these posts by Travis!

    Quick question for Travis – What type of work do you do so that you are able to work remotely for such a long period of time? I have healthy miles/points balances and try to do several trips a year, but I’m always limited by the 3 weeks of vacation time given by my employer.

  3. this is what i’ve also been doing for years now. friends always ask me how the heck i can afford to travel so much and i tell them (along with schooling them to the miles game) that it’s all about finding a bargain. sooner or later the place you’ve been itching to visit becomes affordable. and once you explain to someone that they could spend a weekend dining out and drinking here in nyc OR get flight + hotel for a weekend in ______ for the same cost, they tend to see the perspective.

  4. Travis, you need to take the plunge and move overseas! Apparently, you have the luxury of being able to work from anywhere. Think of all the travel travel/cultural opps.? Plus, you can be on Househunters Int.’l!

  5. That’s all great for you, but I knowingly and deliberately do the exact opposite and pay a premium to go where I want when I want. What’s the point of being a grownup and having grownup money, otherwise?

    So let’s cut to the chase. No matter what anyone says, many if not most are stuck with having to work around school and work calendars. That’s the “when.” And no matter what anyone says, going to Sweden or Viet Nam is simply not the same as seeing the Louvre, the British Museum, the Prado, the Uffizi, or any number of other truly “must see” cultural attractions. That’s the “where.”

    Flexibility is great, of course, and the more the better, but it’s not always possible without leaving just way, way too much on the table.

  6. @ Tom: Certainly, if you have the means and don’t mind the price premium, then you’re exactly right, go where you want, when you want, how you want. To each their own.

  7. Bill — We also really like Europe in the winter. I actually have a picture of me standing in front of the Mona Lisa when no one else was in the room!

  8. Pavel — absolutely agree about a night out or a trip. My wife and I dated long distance for 2.5 years. One of us flew every other weekend. People thought we were crazy. I pointed out that it costs about the same for one of us to fly to visit the other as it did to go out on a “real date”. (Whatever that means…)

    (Of course, the key is that you can’t fly AND go out when you get there….. but that’s never been our thing anyway!)

  9. Matt: My employer has generous alternate work schedule and work from home policies, as well as a fairly generous vacation allotment (at least by American standards). For example, we can chose to work 9/80’s or 4/10’s, instead of a standard 5 day work week. Essentially that allows me to take one day of vacation and create a 4 day weekend…. perfect for a quick trip to Europe in the winter!

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