Footloose and Fancy Free… Or are we?

The truth about traveling without itineraries

For most people, traveling isn’t just a spur of the moment thing. If you are in a couple, normally one party is spontaneous and one is a planner and they get together and balance each other out so travel is a little more thought out. You see people on the internet saying “just book the trip, you’ll figure it out” and “if you jump on this deal in the next 48 hours you’ll save a ton” and it looks fun and crazy and some people look at those images and wish that could be them. There’s a romance to grabbing a carryon and just going somewhere with no plan, but there drawbacks and some pitfalls that not everyone talks about.

For Ash and I, while we both can be very logical and good planners, when it comes to travel, we both like to wing it. In different ways often, but we both wing things. So our travels can look a little haphazard and chaotic at times. We love the adventures though that we end up doing, the places we see and the people we meet but sometimes even we could use some structure.

“Traveling without Itineraries” started out as kind of a joke for us but has become our theme for how we explore. Thats not to say that itineraries are bad, or that a properly planned trip is something we don’t like. It’s more like we have real FOMO when we travel. So if we’re on a schedule, we often look around at the other things around us wondering what we COULD have done instead of the planned activity we currently ARE doing.

This comes with a series of arguments both for and against obviously.

“If you plan better, you won’t miss anything”
“Just make a list and go back later”
“Heck yeah! Experience everything you can!”
“You never know when or if you’re back so do it while you’re there”

We smile when we hear both sides of the arguments because we’ve heard them all before and we have learned the hard way in both situations. We have had trips where we wish had planned and we’ve had trips where we barely slept but we truly felt like we got the most authentic experience possible. We have friends who plan everything, friends who like to vacation simply, and friends who like to go on trips where they don’t have to think and the cruise director or trip organizer tells them what they’re doing day by day. There is nothing wrong with any of these at all, it just turned out for Ash and I that 90% of the time we prefer to wake up someplace and pick a point on the map and go.

It’s been said that the most dangerous word in the English language is ‘Someday’. Someday is just code for NEVER. It’s a platitude that we use to tell ourselves that everything is possible and we’ll get there someday.

For some, they can do it all. For most though, they have a Pinterest board and two weeks of PTO a year and they try to see the best things they can while stretching the dollar as far as possible.

After our time working in the resort industry, nothing scared Ash and I more than SOMEDAY. We killed our selves each season just to get to the end and take off for a week or two and then come back to do it again.

FULL TRANSPARENCY
Now to be completely honest, this style of travel is hard. Ash and I don’t have money, we bust our butts just to take the trips we do take and traveling without a plan can be costly. We have had some trips where we saved money because we avoided tours and planning, and we have had trips where our day by day style definitely incurred more cost than we had anticipated which always puts a pinch on things.

When we go someplace, it generally looks something like this:

Pick a location
Book a flight there
Choose 3 things that we would like to do
Find a place to sleep the first night
Thats about it.

Maybe that sounds like an itinerary to some, but that’s about as far as our planning goes. We frequently book our nightly stays while en route to the next location, very commonly on a travel site or just walking in and asking about vacancy. We’ll stay anywhere so it’s never hard to find a place to sleep. Truth be told we’ve lost reservations and money before due to travel problems with airlines so we have a small bitter taste in our mouths about having a full plan. lol.

By choosing just three things we would like to achieve while we’re there, we leave ourselves open to any number of adventures. For instance, on a trip to Ireland not too long ago, we flew into Dublin and the goals were pretty simple. Get to Northern Ireland by train to see Belfast, go to Bushmills in County Antrim, and see the Giants Causeway. In between all that, we left time and days open to do anything else.

TRUTH TIME
We love to travel like this, but if we’re being honest, it takes a toll on you. You end up very much living out of a duffel bag or rolley bag (depending on your style) day by day and sometimes you end up in a city, town, or hotel that looked neat or you heard about online but you don’t actually enjoy all that much.

You’ll be tired. Very tired. It takes a day or two to catch up on sleep for sure. If vacationing is your style as opposed to traveling, this hopscotch style may not be for you.

You’ll incur unforeseen expenses. This is just a reality. As long as you have some contingency built in, you’ll be fine. Maybe you overpaid in one town, so hopefully you make up for on the next one.

The point of traveling like this is building memories, scratching things off your bucket list, and building some resilience.

After all, the sun comes up and the sun goes down and you can have another adventure tomorrow.

If you’re thinking about trying this out, maybe start small with a road trip from where you live. Then if you’re going overseas and you don’t speak a second language, maybe choose an English speaking country to try this in so you don’t have to try to navigate a foreign language at the same time you’re booking your next sleep spot while the train conductor is punching tickets.

At then end of the day, traveling is one the best things you can ever do. So as long as you’re getting out there and you are comfortable, that’s all that matters. We know we are biased but we cannot recommend this style of travel enough!

We encourage you to try it at least once just to see what it’s like. There’s a freedom in traveling like this that doesn’t come with pre planned excursions. You are able to immerse yourself more fully in a place and a culture and see things that you probably wouldn’t have seen otherwise. Or you’ll discover a town that like a movie that didn’t get the best reviews, YOU actually ended up liking! Just because one person said it wasn’t great doesn’t mean it won’t be great for you.

Let me leave you with this; take SOMEDAY out of your vocabulary.

If nothing else, maybe take a four day weekend and road trip to a town you’ve always wanted to see.

The recipe for adventure from what we’ve discovered goes like this:
A little chaos,
a little less sleep,
a pinch of the unknown,
and a willingness to try new things.

This is what makes memories.

If you can handle a little bit of the unknown, there is a romance to just hopping on a flight and figuring things out. Give it a shot and let us know how it goes!
See you out there!