Why Winging-It Beats a Fully Planned Itinerary

My husband and I prefer to wing our trips in some way or another: sometimes we plan a few things we’d love to see and/or do but overall we play it day-by-day.  In this post, let me tell you why we’ve found that winging-it travel trumps fully planned travel.  This includes booking lodging, tours, excursions and activities last minute as well!  Believe me, it always seems to work out for the better.  You may be thinking, “Well, don’t you write travel guides?”  Why, yes I do!  However, I always intend for my guides and writings to inspire your travels and give advice, not to dictate and map out each day and step of the journey for you.  After all, planning can only get you so far.  I believe a great traveler is meant to be open to receiving whatever comes their way – open to all the universe’s unexpected glory.

“A good traveler has no fixed plans
and is not intent upon arriving.” – Lao Tzu

You have the freedom to discover and choose.

When we have NO set destination, we’re able to roam as we please and discover things we may never have known existed, cue: open to finding hidden gems.  AND, if we happen to fall in love with such hidden gems and happenstantial discoveries, we’re able to enjoy them for any amount of time because our itinerary is open.  We don’t have any set place to be or any obligation to race against time for.

On our most recent road-trip out west, we didn’t book ANY campsites or lodging ahead of time and it ABSOLUTELY worked in our favor.  While we were in search for a place to camp on our first morning in Glacier National Park, we discovered the coolest campsite ever!  It was a first come, first serve camp and had we booked our lodging in advance, we would’ve never been in pursuit for such a site to begin with.   Not to mention, you can’t book these type of sites ahead of time.  Almost all of the incredible campgrounds are first come, first serve.  We’ve ALWAYS found the most amazing campsites when we didn’t plan ahead.  Rather, we stumble upon these treasures and afford ourselves this freedom to discover and choose by NOT planning.

Photo Sep 04, 5 30 37 PM
Campsite in Glacier National Park.  Photo by: Doug Michaels

Still photo above taken from GoPro time-lapse thanks to these tools below:   



Furthermore, my  husband would’ve never discovered one of our favorite places in the country had he planned his Colorado journey in advance.  He and his buddies were wandering through the Colorado Rockies when they stumbled upon a dirt road with the end destination reading “Twin Lakes”.  Opting to take this adventure on, they explored the area and uncovered the most gorgeous and secluded place to camp (for FREE).  Even more, there is also a campground nearby that has a vault toilet and costs $10 per night.  The campground rests directly beside the lake and is totally encompassed by massive mountains (the largest in the Rockies).  Loving it SO much, he brought me to this exact place a couple years later and I, in return, brought my best friend here a few years after. Each visit, I’ve been in utter awe of this place’s beauty.


Recommended tent:

What if I can’t find a place to stay?

This question is what worries most people and is a main deterrent to winging a trip.  So, let me put your worries to rest by telling you: This has NEVER happened to us.  Even when we visited Banff National Park – one of the most popular tourist destinations in Canada – on their national holiday “Canada Day” (equivalent to our Fourth of July), we STILL found a spot to camp for three nights right beside the park’s entrance and situated on the outskirts of the town Canmore.  This prime spot allowed us to walk to the bars in the evening (to celebrate Canada Day, duh!) AND allowed us easy access to the park in the mornings.

BLM Land

You can always take advantage of BLM land.  BLM lands are U.S. Public Lands that make up approximately ten percent of the country.  Most allow you to stay, free of charge, for 14 days before you have to move onward.  Merrow Creative recommends using Benchmark Maps when camping among BLM land and National Forests (and I agree).  These maps are great for giving you loads of information on these lands, including scoping out dirt roads and providing clearer boundary lines + more!

Save Money

Even when we’ve traveled to international cities like Amsterdam and Bruges, we booked lodging last minute.  We tend to find the most phenomenal deals on lodging sites when we wait vs. planning ahead.  We simply search for the “hot deals” or the “express deals” on apps such as HotwirePriceline, and HotelTonight.   I can’t express this enough: Utilize these tools and you will find incredible deals that will save you money.   Just another perk to winging-it!


When bad weather strikes…

Photo by: Doug Michaels

Photo taken with:

True, not every trip goes as planned.  Precisely why you shouldn’t plan it all!  What if you book a full itinerary revolving around enjoyment in the great outdoors and BAM! a giant, relentless storm rolls in?  This exact scenario happened to us during our time in the Canadian Rockies.  We were lucky enough to enjoy a couple beautiful days in Banff and Yoho National Parks, but we still had our sights on much more.  We had hopes of driving the entire Icefields Parkway into Jasper National Park and spending some days exploring there, too.  However, mother nature was not having our (soft)plans.

The morning of our supposed departure to Jasper, we woke up to constant downpour (carried on from continuous showers over the course of the entire night).  We consulted the forecasts and radar maps and saw absolutely no end  to the rains for the next couple days. Thus, we readily formed a solution: outrun the dreariness and head some hours south.  We added a completely new destination onto our trip because our wide-open itinerary enabled us to do so.  In this instance, we were immensely grateful that we hadn’t formulated strict plans in advance.

I believe a good road-trip affords you to pick up and just GO; wherever you want and whenever you want.  No fixed plans.  No set agenda.  The ability to freely roam beautiful and diverse lands near and far with the start of your car.   And it, my friends, feels divine. The FREEDOM is like none other and it is the exact excitement, spontaneity and thrill my soul yearns for.

Photo Sep 04, 4 55 32 PM
Lake Moraine in Banff National Park. Photo by: Doug Michaels

Shop my hiking boots:

Take advice from the people you meet along the way.  Jump on opportunities as they arise.

I can’t count how many times we’ve met locals who have recommended places to visit, unheard of by most.  Allow yourself the openness to heed these recommendations.  After all, who knows the land better than a local?  When we traveled around Iceland, we stayed with several unbelievably generous hosts who would talk with us at dinner/breakfast and reveal unknown spots for us to explore and unknown facts about their way of life.  It was all so fascinating!  Ultimately, these are the type of experiences I seek out when traveling.  Therefore, allot yourself the freedom to discover things you may not have formerly engraved into your rock-solid itinerary.  In other words, don’t have a rock-solid itinerary because it only subjects you to being close-minded and closed-off to brilliant, genuine experiences.  No one wants to have to reply to a great recommendation/discosvery with “we can’t do that because we already have ____ planned“.


Expectations can ruin a place or experience.

While it is great to have hopes and dreams, when you fully plan the trip of your dreams and expect things to go according to your plan, you are setting your trip up for failure.  You’re building up this idea in your mind of what your travel has to be vs. what your travel experience is meant to be.  Even more, you are limiting your journey’s full potential.  Of course, have places in mind to visit and experiences in mind to enjoy.  But, don’t let your grand plans become the be all, end all of your travel experience.  In all my travels, I’ve acquired this wisdom:  have a list of “like to’s” but not “have to’s“.


For our recent road-trip out west, we knew we’d like to explore, hike and camp in: Banff National Park and Glacier National Park.   But we did not plan anything other than hopping in the car and driving to Banff, Alberta, Canada.  We didn’t plan specific lodging, specific hikes or a specific amount of time in each place.  There was no place we had to be or a single thing we had to do due to a set itinerary and prior bookings.  We wandered for as long as we liked in each destination, then moved on to the next.  We may not have liked the weather and hindrance of our Jasper exploration, however, we liked we were able to move to better weather.  We discovered how insanely jam-packed with tourists Banff National Park was and liked that we could decide to hike in its less-populated neighbor, Yoho.  Had we been dead-set on exploring Banff (only) we would have never uncovered the glory of Yoho (which I ended up loving more)!  Openness is key.

All in all, we were free to discover, first hand, the beauty and adventure these places had to offer.  As a result, we had no expectations and thus, experienced the BEST of things.  We hiked the BEST hike we’ve done to-date, we camped in one of the COOLEST sites to-date, we encountered the most INCREDIBLE wildlife to-date.  It was all MEANT to be.  It didn’t HAVE to be.  I had some of the most magical experiences by merely letting go and letting it all just happen.

Check out my posts regarding this past trip and the BEST hike + most INCREDIBLE wildlife experiences I’ve mentioned above:

The 5 Highs of Hiking the Highline Trail

Find Me Where the Wild Things Are: Yellowstone National Park


Snag my hat above (one of my favorites!):

I truly hope this could help inspire some of you to let go of your structure and expectations and try a more wing-it style of traveling for your next trip!  I’d love to hear about any incredible lessons and opportunities that winging-it afforded you.

As always…

Much love and happy travels!


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