Travel Planning is so Overrated


My first big trip away from home way back in 1998 I planned nothing, and look how that turned out?  I knew where I was going to stay, and how I was going to get there.  But that was about the extent of my travel planning skills.  Plus the internet wasn’t actually a thing back then, but with the gaining popularity of the internet, and fear of what happened in California you would think I would turn into a “Plan everything” kind of guy.


AVOID TRAVEL PLANNING OR YOUR NEXT TRIP PACKING DAY MAY LOOK LIKE THIS MESSOn occasion, I have been the “overpacked” guy, but never the “plan everything” kind of guy.  I have learned over the years that nomadic life works out in the end, and mishaps are just part of the adventure.  Planning a journey is actually a pitfall because now you’re on the clock.  Deposits are at risk, and anxiety overtakes your trip.


Years of adventure travel have made me much better at just going with the flow.  I’m a last minute travel planner who has never had any set itinerary.  When plans change or things go wrong I just roll with it because from my experience it just adds to the adventure.  And the alternative to dealing with it will have you curled up in a ball of stress and anxiety trying to figure out how to get back on schedule.

Traveling without a plan allows you incredible adaptability to take advantage of opportunities you wouldn’t otherwise be able to.  It allows you to pivot to other options you couldn’t find on the internet back home, or change your mind when something different comes along.  Letting your trip unfold randomly can lead to exciting and unplanned adventures.


I set my heart on Florida one winter but ended up in Outer Banks North Carolina where I made the most money I had ever made in one season. I met a girl and bought my dream truck!  Another time,  I found myself in the middle of a civil war in Bangkok so I bailed.  That lead me to Grand Teton National Park where I found employee housing for $210 a month, and a $1200 a week job in one of the greatest landscapes in America.

ADVENTURE Travel Life QuotesI wouldn’t have had these or many other experiences had I planned an itinerary with a set schedule.  I recently wrote about a hail mary road trip I made to change my situation where I drove from Montana to Arizona in the hopes of finding that summer money in the winter months. After struggling for longer then I wanted to I stretched up to South Lake Tahoe only to find locked doors of opportunity!  Which at the time had me frustrated.  Especially since I had to drop Kota and the RV off in Minnesota, but now I reside in the Grand Canyon.  I have a job that pays close to $40 an hour and charges me only 45 cents a working hour for housing.  I’m on another working vacation in one of the seven wonders of the world because I traveled without a plan, and let the adventure unfold.  Travel planning wouldn’t have gotten me to the Grand Canyon, or see my old friend in South Lake Tahoe.


Most new travelers are the opposite as they over plan and over pack.  I understand why people schedule their entire route sometimes down to the specific hour, or even why they overpack.  Its because travel planning is intimidating and they are afraid of the “what ifs”.  I was afraid too at one time.  What if I meet someone who wants to go to the beach, and I don’t have any shorts?  Or what if I get there and the tour is overbooked because I waited to find a better a deal in person? Travel life has a way of providing you everything you will need to have the greatest experiences & best adventures.  Alaska taught me that.


My first season in Alaska I packed city clothes.  No sleeping bag, no tent, camping gear of any kind.  Surrounded by hippies & vagabonds there I was with a suitcase full of Khakis & dress shirts.  All I needed was a pair of jeans, tennis shoes, T-shirt, sleeping bag & a hoodie.  Instead, I had 4 suitcases of useless clothes and gear.  This last move I packed one bag of clothes, and still brought too much.  I packed it in under 10 minutes 15 minutes before I left, and I still over packed.  Life on the road will teach you that all you need is the basics.  Everything else you can buy, make do with what you have or it will emerge from the people you meet along the way.  Don’t over think your travel planning like most rookie travelers do.


Travel without a plan and traveling slow through Jackson Hole & grand Teton National ParkWhen it comes to travel less is more, and slowing down is the best travel planning advice anyone can give you.  Traveling slow creates opportunities for happy accidents of travel where you find yourself on amazing adventures you wouldn’t have otherwise been exposed to.  Spending more time in one destination allows you to get a better feel for the pulse of the rhythm of life in the area, and meet amazing locals that will turn into travel angels.

I have a friend that prays for things to go wrong because his best memories are from the worst scenarios.  He is a strong believer in “The Adventure starts where the planning stops.” So plan your route and fill in the blanks along the way.  You’re going to meet like-minded people at every hostel you stay in, and there’s another hostel just down the road if you don’t like what you find at the first one.


When you overplan your trip you miss out on great attractions like this mountain landscape I found while slow traveling through Grand lake ColoradoTravel planning trips can be exciting and adventurous.  When you start out you’ll be overzealous and try to cram everything in.  That’s ok.  Consider this your rough draft, or what I like to call a highlights reminder.  These are the things you want to see and do but take a deep breath.  Realize its unrealistic, and burdening to try and rush from attraction to attraction.  Plus costly.  The slower you travel the cheaper things are.  Taking a taxi from the hostel to the Eiffel Tower is practical, but what will you uncover walking the 3 miles through the city of Paris from your hostel to the Eiffel Tower?

The best advice I can give you for a trip or travel planning is to figure out the destination.  Then figure out your direction, and slowly start moving that way.  Book your first few nights of travel.  This lets you get a feel for the vibe of the layout around you.  Then let the adventures unfold from there.   Slowly travel from destination to destination until you feel like stopping or changing direction.  See the sites on the way, make new friends at the hostels you find, and take notice of the little things.


TROVER the greatest travel app on the internet. A digital travel guide that never goes out of date, and every traveler, backpacker, nomad, vagabond & world traveler should have own this travel appGo with the flow, and follow your highlights list.  Or better yet let Trover guide you.  Its the greatest guidebook ever invented,  and never goes out of date.  Trover is perfect for travel planning on the fly.

When it comes to trip planning there is no magic answer., but there may be a universal approach to keep you focused and stretch your budget.  Whether it’s through a city or country simply keep moving forward.  Travel in a continuous loop, and avoid doubling back.  This way you can keep your transportation costs down, and use your time more efficiently.  Keep your plans flexible so that you can stay in a destination longer or leave sooner if you find a better adventure.


Every long-term traveler has done their fair share of travel planning and will tell you:

“Life on the road will destroy even the best-planned trip.  When the unexpected happens thats when you will find yourself in a great adventure story you can tell all your friends back home someday.”

From breaking your hand, traveling to new destinations with new travelers, vehicle breakdowns, losing reservations, staying longer, leaving sooner, finding love or even finding you’ve been robbed unexpected things happen on the road of travel.  Roll with it, and move on.  Dwelling on it will only wreck your trip.


Be flexible when trip planning AOWANDERS TRAVEL BLOGBe flexible because if your not the only thing your going to find is stress & anxiety.  Don’t rush from attraction to attraction.  You traveled all that way so soak it in.  Enjoy the moments and leisure of life while on your trip. Its ok to create a vague plan or even a backup plan, but be flexible or you’ll regret it later.

Travel is meant to be leisurely, exciting and adventurous.  If you get overwhelmed, burnt out or just want to relax for a few days or take a “travel-time out”it’s important to give yourself some wiggle room in your travel schedule to do so.


It’s important to give yourself flexibility for destinations you like or dislike so you can stay longer or leave sooner.

The best travel plan is a flexible travel plan that gives you direction and adapts to your likes or dislikes while on the road.  Traveling with a vague plan is ideal, but traveling without any plan is even better.

Check out these articles to learn how not to overpack, travel gear, travel planning  & prepare for long-term travel.

Prepare for long term travel

What to Pack for my trip.

Travel Planning

Travel Gear

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  • I love this post. I’m with ya on it. Just enjoy the trip. Too much planning and trying to stick to a tight schedule sucks the joy out of anything, and your trip is supposed to be fun.

    You have some beautiful pictures here.

    • Terry,

      Thanks for stopping by my travel blog. This is one of my favorites because I am always telling people to stop planning so much, but I understand the reasons why. Comfort zones and all, but after you take one trip without planning anything you’ll never plan again. My next big trip is a 43,000 mile camping road trip pretty much from the top of North America to the bottom of South America, and the only thing I’m planning is down the East coast up the West Coast hahaha 😀 😀 See what happens in between. Are you in the process of sketching out a trip?


    • Elisa,

      Thanks for stopping by. Trover is the social media platform that has somehow slipped through the cracks, and its really unfortunate because it has so much potential for businesses & users. If you ever find yourself not knowing what to do trover’s got your back. In any city for any activity. Its truly a wonderful platform. Glad I was able to introduce you to such a wonderful tool.


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