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Why a Solo Road Trip Is the Best Confidence Boost

Road-tripping as a solo female traveler can lead to an interesting range of experiences and emotions – from self-doubting lows to confident highs. Undoubtedly, the first time you embark upon a solo road trip, you’ll face a range of obstacles, discomfort, and challenges. But, that is precisely what makes road-tripping alone such an empowering experience and why it can bring such a powerful boost to your self-confidence.

By Camila Castro

Choosing a New Experience

As an avid world traveler, I was excited but also a bit apprehensive to embark upon my first solo road trip. Having done plenty of traveling on my own, this seemed like the obvious next step in becoming an even more independent and experienced solo female traveler. The chosen destination for this trip: Hawaii’s Valley Isle. This was a deliberate choice, as it seemed like an adventurous destination that would inspire and challenge me, but also felt familiar and safe enough to undertake the trip all by myself.

I tend to be a very independent travel planner but, in this case, I chose to work with a travel concierge to design a customized itinerary for my 10-day road trip around Maui. Something about putting the planning for this new travel experience in somebody else’s, very experienced, hands, took some of the anxiety out of the idea for me. I was going for a balance between stepping out of my comfort zone and having a replenishing experience, and my itinerary perfectly met those desires. It seamlessly shifted between activities like; going on a solo hike in Haleakala National Park one day – not something I’m prone to do on my own – and blissing out at a Lomi-Lomi spa the next – a much more up-my-alley experience.

The Road-Trip Begins…With a #Fail

Upon arriving at Kahului Airport, I had my first moment of doubt when I struggled with the contactless car rental process. For a few moments, I felt pretty useless, questioned all of my faculties, and thought I might spend part of my Maui vacation at the airport parking lot.

Eventually, I was able to retrieve the car keys from the lockbox and, relieved, was finally on my way to my Lahaina B&B, but I still felt somewhat foolish and glad no one had been around to witness my first #fail of this trip. I wasn’t off to the best start but things had to get better, right?

The rest of my road trip unfolded in a similar manner. I would follow my detailed itinerary, driving my rented Chevy around the island, having adventures and making discoveries along the way, feeling pretty in control – like an independent travel rockstar – until something unexpected would happen that derailed my carefully-made plans and me freak out – like taking the wrong road back from Hana, which apparently only the locals are intrepid enough to drive.

I would immediately spiral, and start to doubt all of my prior travel expertise, questioning my choice to road trip by myself around an island I wasn’t familiar with, wondering if I was doomed to spend my time in hotel rooms, paralyzed with fear and self-doubt. Until my rational side re-engaged, my inner wisdom emerged, and I would figure out a way to either resolve whatever the obstacle was or just go with the flow and see what happened. Inevitably, things worked themselves out and my solo adventure around Maui continued.

Confidence started to creep up on me as the days passed. Before I knew it, I was feeling empowered, sure of myself and my ability to road trip solo. Self-trust flooded back into me and I could identify as a capable solo female traveler once again, fully able to drive my way around Maui on my own. It was an interesting see-saw of emotions, choices, and agency that reminded me why solo travel can be such a powerful teacher and how these often uncomfortable experiences can give such a beneficial boost to our confidence.

Lessons Learned

Stay Flexible

Without question, the most meaningful lesson I learned from road-tripping solo was the importance of being prepared, but also the ability to stay flexible. Having a planned itinerary, hotels confirmed and even a few dinner reservations booked, gave me the peace of mind to enjoy myself and not have to worry about where I would be staying or eating. However, leaving room for unexpected experiences, spontaneity, and plenty of time to explore resulted in some of the best moments of my trip – like sitting for hours watching the awe-inspiring surfers and windsurfers braving the massive waves at Ho’okipa Beach, or eating ripe mangoes directly from a tree dripping with them that I came upon on the Pipwai Trail.

You’re More Capable Than You Think

The next lesson that was hammered home, was to trust myself and all that I’m capable of. I feel that, as women, we often don’t give ourselves credit for what we can do and how resourceful we truly are. Despite many moments of concern and, in some instances, even sheer panic – like when I got hopelessly lost in the forests of the Upcountry looking for my hotel without a cell signal as night set in, or when I encountered mud wasps blocking my way on a trail, a major phobia that I had to overcome to continue, or even when I had to drive down Mount Haleakala at night, in the fog, with low visibility, on a road with hairpin turns – each time I overcame one of these challenges, my confidence in my abilities as an independent solo female traveler only grew.

Trust That Gut Feeling

The final crucial lesson I learned in Maui, is how essential it is to listen to your intuition. There is a reason why the concept of “trusting your gut” exists. If I had done this, I might have avoided some seriously scary moments taking the southern road back from Hana to civilization. A road that was, apparently, prohibited in my car rental contract. Sure, I got some spectacular views. But, I also put myself in a highly stressful situation that could have been easily avoided if I had just gone with that gut feeling and taken the regular road back from Hana, as most tourists do. Your intuition will not lead you astray, especially when you find yourself in unfamiliar surroundings, alone. That inner voice will always come through for you, so heed it!

Road-tripping solo around Maui not only opened my eyes to the limitations I sometimes place on myself, but it empowered me to continue embarking upon solo adventures, even when they scare me or when I doubt myself…especially when I doubt myself because, now, I know I can lean on my confidence to see me through.

Ever thought about embarking on your own life-changing solo road trip? Trips like this are just one of the reasons I decided to become a Mindful Travel Coach. I love working with my clients to help them move past their limitations, trust themselves, boost their confidence, and use their travels as a tool for personal growth…because, in the end, that’s what travel is all about, isn’t it?


January 2023

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