Hitchhiking The Skies - Flying With Travis And His Family

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.

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.

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.

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!

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.

@ 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.

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!

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!)

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!