How I Ended Up On My First Solo Trip

January 8, 2019   5 Comments »

How I Ended Up On My First Solo Trip

January 8, 2019 5 Comments »


In an effort to bring you some new voices on Ottsworld, here is a guest post from blogger Jackie Sills-Dellegrazie. I met Jackie recently at a Blog conference and she so nicely said to me, “you inspired me to travel solo!” I was so touched as I heard her story of her hearing me speak at the New York Times Travel Show and her first solo trip! I asked her to share that experience on my blog since I think so many women out there can relate to overcoming the fears to travelling solo! I hope you enjoy her story as much as I did! All opinions and experiences expressed here are hers. –Sherry


I’d been feeling that relentless urge to travel more for a while. It was a restlessness I couldn’t shake. An idea doing laps in my mind searching for a nonexistent finish line.

As a teacher, I had more time off than my husband, family, and friends and I was frustrated letting my 2-week long breaks and summer vacations come and go because no one else had the same amount of time to travel.

I’d browse traditional travel publications like National Geographic Traveler or search for a random episode of Samantha Brown’s PBS series to transport myself to a medieval European village or to a far-flung place like Malaysia’s Borneo hoping to spot a pygmy elephant.

But despite feeling beyond inspired to see the world, the thought of traveling alone really hadn’t crossed my mind. To be honest, I had no awareness at all about the world of solo female travel or that plenty of women were out there seeing the world on their own.

solo travel inspiration

Solo Travel Inspiration

So imagine my surprise and intrigue upon going to the New York Times Travel Show (a no-brainer since I live in NYC) and seeing a seminar on the schedule that included a panel of women who had traveled solo all sharing their experiences.

It was early January and my next school break would be in late March. I circled the panel discussion on my schedule with the urgency of someone who knew all too well how quickly that next bit of time off would arrive. Call it a gut feeling, an aha moment, or whatever you’d like. I knew at that moment whatever these solo women travelers were about to share was my ticket to something big.

I gripped the edge of my seat trying to memorize every word as a woman named Sherry Ott told how she’d quit her corporate IT job to travel the world on her own. I was awed by the writer from Fodor’s who told about her solo hiking adventures and by another woman who had spent months backpacking Southeast Asia by herself.

At the end of the discussion, interested and curious women in the audience stood up to ask the panel all kinds of questions. I just sat listening, letting everything I’d heard process in my mind. When the seminar ended, I squeezed my husband’s hand in excitement and gave him a look I know he understood. My bags were already packed and I was about to furiously plan and set off on my first solo trip.

Go Big or Go Home

While I may not be an early adopter of most things, I have always been a go big or go home type of girl. In the case of traveling solo, I was probably one of the last people on the planet who realized it was something I could do. But once it was on my radar, I was all in.

first solo trip patagonia

Forget London. Forget Paris. Patagonia sounded like the best choice for my first solo adventure. Yes, as in the end of the world, the southernmost tip of South America, that Patagonia. Had I been to anywhere in South America before? Nope. Did I speak Spanish? Nada.
But, I’d seen some epic photographs of Patagonia’s mountains and glaciers and I just had to see them with my own eyes. I’d chosen destinations before based on a few incredible photos and a hunch while planning non-solo trips and hadn’t gone wrong yet.

Not only that but I was so convinced traveling solo was the answer I’d been searching for that while booking my flights to Patagonia, I figured why not also book a flight to Thailand for a future solo trip!? When I say all in, I don’t kid around!

First Solo Trip Jitters

Fast forward to my 2-week spring break and airplane wheels touching down in Santiago, Chile. The sun was rising and the red Andes Mountains around the airport looked ablaze. I’d planned a day in Santiago before flying down to El Calafate in Argentina to begin my Patagonia adventure.

But as I took a taxi from the airport to my hotel, I wasn’t feeling so confident. The butterflies in my stomach had morphed from swarming nerves into a full-fledged, kaleidoscope of OMG fears.

I checked into my room and tried to compose myself. I’m a master of finding all of these things to do when I’m trying to avoid something. Suddenly, I had to rearrange my bag. My sneakers needed to be re-laced. Did I brush my teeth? Can’t remember, so let’s brush them again.

In reality, I’d planned to do a late morning free walking tour to see Santiago and learn more about the city but I was having trouble just convincing myself to walk out of the hotel room!

Free Walking Tours are a great way to start a solo trip!

See this and other Tips for Traveling Alone for the First Time here

The fear I felt took me completely by surprise. I’d traveled out of the country before, just not alone. For Heaven’s sake, I moved to New York City on my own at 18. Where was that courage and bravado now?

I realized I was going to have to take it slow, at least initially, or else my fear could consume the entire trip. Small victories to build on each other was my strategy. I settled myself down a bit with some deep breaths, but also told myself in no uncertain terms, this is happening. You can do this.

I put together my daypack, going through a safety checklist in my mind. Passport and emergency funds locked in the safe. Money and credit cards for the day stored in a hidden pocket as well as inside my daypack. I studied the map for a couple more minutes to confirm I knew where the walking tour meeting spot was in relation to my hotel.

And then, I did it. I walked out of my room, through the lobby, and out into the sunny Santiago morning.

Looking back, and now having read many other accounts of women who’ve traveled solo for the first time, I know my fears were completely normal. In fact, it’s become a pet peeve of mine when I see bloggers and writers who glamourize solo travel without telling of their fears and nerves.

Don’t let Solo Travel Fears Win

first time solo trip

Everyone gets them. I’ve taken plenty more solo trips since this first solo trip and still feel some jitters in the beginning. These fears have the power to sabotage your solo travels but you mustn’t let them. There’s far too much to gain by pushing through them.

I made it to the walking tour meeting spot and had a great several hours exploring Santiago. Introverted little me even ended up having an early dinner at an outdoor cafe with an Irish couple I met on the tour! Compared to how the day had started, I was feeling steadier and more confident by sunset.

Read how to overcome travel fears

Solo Travelers Can Rely on Others

The next day was an entirely new day, though. I was heading back to the airport to fly to El Calafate to begin my Patagonia adventure and I still had a lot to learn.

Two of the most common things solo travelers will tell they’ve figured out from their experiences are how to solve problems by thinking on their feet and how most people are genuinely kind and willing to help when you need a hand.

patagonia solo travel

Standing at the Aerolineas Argentinas check-in counter for my morning flight without my printed visa paperwork (no longer needed by the way) to enter Argentina, I was told I couldn’t check in or board my flight. My trip could have started off with a missed flight and a messed up itinerary. Except I wasn’t going to let that happen.

Travel hiccups can really throw you off your game. If you travel enough, you just come to accept them as part of what happens. But on this trip, I was hardly a travel pro. Luckily, the previous day had ended well and I summoned enough wherewithal and determination to calm myself down and keep my trip goals in sight.

Connecting my phone in the airport to go through the necessary steps on the Argentinian website to get my paperwork was nerve wracking, to say the least. The signal wasn’t great and pages were loading slooowly. Not to mention, all around me other travelers continued to check-in for the flight.

I knew I would need to print the visa document and hadn’t quite worked out how that would happen yet. Kicking myself for not taking care of this before I left NYC wasn’t going to help now.

With the online portion complete, I returned to the airline counter. This time, I spoke with an older gentleman who was much more helpful than the first agent. Without having to ask and completely understanding my issue, he ushered me to a back office within the airport where he let me use his computer to log in and print my paperwork. To this day, I’m forever grateful to this man. He saw my problem and went above and beyond to help.

Solo Travel in Patagonia

argentina travel

It was also reassuring. I was traveling solo, yes, but I wasn’t really alone. This reaffirmed itself again and again throughout my 2 weeks in Patagonia. Whether it was my new Argentinian aunties who befriended me on a long bus ride to the Chilean side of Patagonia and saw it as their duty to make sure I got through the border control checkpoint without issue and back on the bus in time. Or the bus driver who knew (from no fault of my own) I’d miss my connecting bus to get down to Ushuaia and radioed the other driver to work out a random meeting spot literally in the middle of nowhere so I could switch buses. And even the local family who ran the hostel where I stayed in Puerto Natales who insisted I message them on WhatsApp to let them know I’d reached my next stop safely.

Throughout the trip, I found the right balance between looking out for myself and placing some trust in the people I met along the way.

You might be thinking, is this all really worth it? Traveling is supposed to be fun and a way to de-stress.

Well, it was all thrills while I was trekking on Perito Moreno Glacier and all smiles eating my lunch to the thunderous sound of ice chunks calving off the front of the glacier.

perito moreno glacier solo

Hiking in Los Glaciares National Park in El Chalten, Argentina on the Laguna de los Tres trail brought me past some of the most beautiful natural landscapes radiating with the reds, yellows, and oranges of Fall and to one of the best viewpoints to see the spectacular spires of Mount Fitz Roy.

Horseback riding in the mountains above Puerto Natales for sweeping birds-eye views over the Chilean fjords is only outdone by my time spent in Chile’s Torres del Paine National Park. Imagine soaring mountain peaks, lakes full of turquoise water and floating crystal blue icebergs, and vast grasslands where guanacos graze…and sometimes pose for photos.

And the pride I felt having navigated all of those South American buses to make it to the southern tip of Argentina to the Tierra del Fuego and Ushuaia! I was so excited I made a last minute hotel switch to stay somewhere just a tad bit nicer.

It worked out, too, because it was just a quick walk down to the seaport to take a boat out into the Beagle Channel to look for wildlife like seals and penguins and explore some of the tiny, uninhabited islands off the South American coast.

Solo Travel Takes You To a New Level

You hear all the time how empowering solo travel is. Before taking this first solo trip to Patagonia, I considered myself a confident person. But, this experience not only brought me to a new level of self-reliance and strength, it showed me how to harness these assets to make my goals, travel or otherwise, happen.

first time traveling alone

If you want to travel and have no one able to join or simply want to experience the world on your own, there’s no reason not to and so much to gain by pushing past your nerves and fears. The world is the perfect canvas for making the unfamiliar familiar whether you travel to an epic destination like Patagonia or choose somewhere that feels more right for you.

As I flew back home, I realized that restlessness I’d felt about wanting to travel more had been transformed into a feeling of contentedness. No, I didn’t discover a magical cure for the travel bug. It was even better. I figured out how to include my wanderlust and urge to explore into my life in a way that honored who I was and what I wanted.

Meet the Author

Jackie solo travelerJackie is the founder of The Globetrotting Teacher travel blog. She’s an avid traveler who’s been to 30+ countries, the 48 continental states, and 6 Canadian provinces. Using her travel hacking expertise, she experiences the world (for less) with the help of miles and points. Whether she’s solo or traveling with her family or friends, Jackie always has her bag packed and a plane ticket booked for her next travel adventure. In between her travels, she lives in New York City with her husband and Italian Greyhounds.

You can follow Jackie’s solo adventures here:
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