Traveling “On The Fly”

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Shawn Reece & Jasmine on a sleeper train from China to Ulaanbaatar, Mongolia.
Shawn Reece & Jasmine on a sleeper train from China to Ulaanbaatar, Mongolia in 2008.

The Wandering Nomad

Those who have been reading this blog for any length of time, know that my travel habits tie directly back to my roots as a backpacker.  Since 2007 we have lived on the road several times and this type of lifestyle makes it difficult to have concrete travel plans.  What if we fall in love with a destination and just have to stay?  What if we planned on spending five days somewhere and hate it? Living on the road means it is best to leave as many options open as possible.  Even for shorter trips, I cannot seem to shake this habit of booking travel “on the fly”.

For most people this type of travel can be difficult. Many people I know, especially those who only take a “vacation” once or twice a year, have to plan everything out in advance. They have to know what hotel they are going to stay in, make reservations each night for a restaurant and will never forget to book their favorite tours or activities. To be honest, sometimes I envy them.  It is difficult for me to commit to anything, even a few days out.

On our recent trip to Japan & South Korea, I had some of the hotels booked in advance because of necessity (Park Hyatt Tokyo), but I still filled in the gaps days before our arrival.  This meant that I could plan the trip based on how we felt at the time of travel and not a year before.

Being flexible and going where the wind blows is the ultimate form of travel freedom.  It invokes that almost dream like vision of the wandering nomad living life to its fullest as he/she wanders about.  Traveling in this way with a child (now a teenager) isn’t quite the same, but it isn’t all that different either.

Shawn Reece & I in Chiang Mai, Thailand ziplining in 2008.  Chiang Mai is a place we loved so much that we had to extend our stay!
Shawn Reece & I in Chiang Mai, Thailand ziplining in 2008. Chiang Mai is a place we loved so much that we had to extend our stay!

Upcoming Travel

This topic is on my mind because I have an upcoming trip for which I have done a ton of research, but haven’t booked one thing.  On Friday, my son Shawn Reece and I will be boarding an Amtrak train from Los Angeles to Chicago.  This much I know.  I still haven’t booked the tickets yet, because I cannot decide on the route.  Decisions decision.  Life is hard.

Do we take the train up to Seattle and then over to Chicago? This would probably be the most scenic of all of the routes, but also the longest.  We could also go up to San Francisco and then to Chicago via the Rockies.  Another spectacular journey I am sure, but one that I have driven before.

Once we reach Chicago, then the real fun begins.  We have no plans.  No where set to go.  Shawn Reece and I have taken three cross country trips, two of them lasting more than a month.  We have been to all of the Continental United States.  With that said, there is so much to see in this country and of course roller coasters to ride as well.  In other words, we have seen the big sights, but there are always hidden treasures to be discovered.

With Chicago being such a giant air hub, there is also a temptation to fly to another country.  Perhaps we could re-visit Guatemala or another country in Central America?  I want to keep any flights to under 5 hours, but the possibilities are nearly endless.  Unfortunately this trip will only last two weeks since I have to return for other engagements, but I love this type of adventure and all of the possibilities it brings forth.

Shawn Reece enjoying the view on a train ride between Mostar & Sarajevo in 2013.
Shawn Reece enjoying the view on a train ride between Mostar & Sarajevo in 2013.

Miles & Points Help

Whatever we decide to do, it will be memorable.  I have always wanted to cross the country on a train.  We have done it in so many other countries, but never in our own.  The best thing about this trip and so many others is that it will be mostly free.  Our train and any plane tickets will be paid for with points/miles and the hotels will as well.  This hobby really has been freeing.  Usually last minute travel can be costly, but it almost never costs me more now.

While some may think I am crazy for not having anything planned on the Monday before leaving, for me it is just normal.  This is the way I have always done things.  This is the way that is most comfortable.  While I am not quite the wandering nomad of legend, I am doing what I love and sharing it with my family.  Pretty amazing!

Sometimes those of us really passionate about the miles and points hobby get too caught up in the pursuit (processes and tricks for earning miles & points) and not in the treasure itself (the actual travel).  Life is about both the journey and the destination.  How I get there and what I do when I am there. How I obtained the miles and the memories I turned them in to.

Where Should We Go?

I will close this out by asking for a small favor.  Where do you think we should go from Chicago?  Help us by suggesting any and all ideas that you have. Not only will I be truly grateful, but I will be covering the entire trip here for everyone to read about! Thanks for your support and have a wonderful week!

Note: Interested in this topic? Don’t forget to read our “Anatomy Of A Roadtrip” series where I detail step by step how I planned and executed our three month backpacking trip through Europe last year.  Part 1 is available with Part 2 coming this week!


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  1. If not Central America, then why not you try island-hopping in the Caribbean? St. Lucia, Jamaica, St. Kitts, etc. Maybe you can have a plane trip in 5 hours or less to the Caribbean or go up north to Canada, maybe not the Canada, but go up to Nunavut, the land above the Arctic Circle?

    Plenty of thoughts for you to think about!

    • Thanks John! We may just head up to Canada. As for the Caribbean, I believe we are going in October with my wife, so I don’t think we will make it there. 5 hours on a plane opens up so many possibilities though! I am excited!

  2. I truly envy you, not only for all the points you have but for being able to do things without planning it out. Even on my recent driving trip that was essentially moving somebody from PA to AZ, I had booked hotels weeks in advance. This turned out to be not the best idea since I ended up driving further a few days and had to cancel some or not get reimbursed because it was priceline.
    I need to learn how to travel like this and not try and plan so much. It’s a hard habit to break.

    As for where you should go, I have no idea but I can’t wait to read all about it!!

    • It takes time and certain comfort level to travel this way. Things can backfire too like the hotel I want not being available since I waited until the last minute. I think the “pros” definitely outweigh the “cons” though. Thanks Gregg!


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