My First Time Was…

Every woman remembers her first time. It can be a thrilling, exciting, scary, emotional and overwhelming experience. Before doing it the first time, her head is often filled with questions. What should I expect? What if I don’t like it? What will it feel like? Will I want to do it again?  When is it right for me to try it? What if I do it wrong? Will they know I’ve never done it before? What will my friends think? Have any of them done it? Is it safe?

I’m of course talking about the first time traveling solo as a female. Because people commonly have a lot of questions about traveling while female, and so many women can feel nervous about their first time, I wanted to share my story and asked some of my closest friends I’ve only met on the internet to do the same. Read their stories of their “first time”, along with a little bit of advice they’d like to pass on. And what stories and tips they have! Though the stories span experiences on almost every continent, the themes are the same. Don’t get in your own way. Don’t wait. Be truly open to new experiences. Enjoy time with yourself. Talk to your mom. Well, don’t let me sum it all up for you, check the stories out below!

My First Time was a Nightmare Gone Right – When I Ran Away to London
Shelby Wollbaum | The Fernweh Wolf 

I was in Vienna.

Aaron, my boyfriend, was leaving after our 2 week European adventure together to fly to Las Vegas, leaving me in this foreign country alone.

It was 3 in the morning when I stood at the hostel door watching him leave to the airport. Once the cab’s tail lights disappeared I realized just how alone I actually was.

I was nervous. Earlier that night we heard a scream from outside the hostel window as well as a loud crack as if someone had fallen out the window. We saw nothing but it left my mind wandering and no sooner did we wake up to the scream did he have to leave.

My first day alone I spent wandering around Vienna unsure of what to do with myself. I had no plans for the next week and I didn’t feel as sure of myself as I thought I would. So naturally I called my mom and asked for advice.

“Do what makes you comfortable,” she said.

So with that in mind I went on sky scanner and started looking at places to go, munching on granola out of a Starbucks cup. On a leap of faith I booked a flight to London that left at 6 in the morning, 12 hours later I was on the plane to what I like to think was the best decision I could have made.

The problem though with booking spur of the moment flights is that it’s not only expensive but it leaves you little time trying to find places to stay. London being one of the busiest places in the world I had to book two separate hostels but luckily they were fairly close to each other.

My first hostel was a nightmare to find and the people staying there were an even bigger nightmare; rude and cliquey would describe them well.

The next day I gladly moved and it was the best experience of my life.

At The Phoenix Hostel it was like a family. I met two New Zealanders, two Australians and one guy from Switzerland. We wandered around separately during the day and met up at dinner time and watched boot-legged movies while drinking hostel beers. The Winter Wonderland was open so one night we spent drinking warm wine in fake snow in Hyde Park and going on rides.

Going to London was the right decision for me. I got my footing at being a solo traveler and then had enough confidence to go to Munich to the Christmas markets where I made friends easily and found my stride when exploring alone.

My advice for the first time solo traveler: Don’t worry about being alone or feeling weird about it. When I was travelling solo I was self-conscious that people were looking at me or judging me when I was taking photos but you have to realize you don’t know these people and they will forget about you in a couple hours. If you do feel uncomfortable though don’t ignore it and do what’s best for you. Be wary of costly decisions but don’t worry if you do make an expensive choice. Life happens.

Something that I always pack that you might not expect: Face mist. When you’re on planes, constantly switching to different climates, being jet lagged or just plain tired your skin can start to feel drained. Face mist is that little refresher I always pack to wake me up and feel, well, refreshed.

Hear more from Shelby: On her blog and Instagram.

My First Time was Life-Changing – Turning 19 the Day After I Arrived in Peru
Mallory Aliaga | Mal’s Away Mallory

Ever since I can remember I had a severe urge to travel, but I just didn’t know where to start. At 18 I was searching for places to go for my first trip anywhere beyond my home country of Canada and neighboring States.

In my searches for your typical European or New Zealand/Australia adventures, I happened upon a volunteering opportunity in the Amazon Rainforest of Peru and I immediately knew that was where I wanted to go.

But how would I break it to my parents. It was 2006 and I’d be a solo female traveler of 18 years old in a country where I didn’t speak the language and didn’t know a soul. After I broke it to my parents, my mom immediately read up on all the horror stories of travelers being raped, pillaged and kidnapped in Peru. Great. Thanks mom.

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Everyone told me how brave I was to go travelling on my own at such a young age to such an unusual choice of country. 10 years ago Peru was very different in terms of tourism. The day after I arrived in Cusco I turned 19. I spent my day with a 26 year old from France and a 60 year old from Denmark and I wouldn’t change it for anything.

I spent time playing with monkeys, building animal enclosures for animals to be released back into the jungle, fished for piranhas, found floating islands, climbed snowcapped mountains, experienced the wondrous Machu Picchu and met the most amazing people with whom I’m still in contact with.

My advice for the first time solo traveler: Try not too plan to much before you leave because if you plan everything to the T, then you don’t leave yourself open to new opportunities you cannot even begin to imagine exist when you are home.

Something that I always pack that you might not expect [or talk about openly]: My menstrual cup. I hate having to bring along pads or tampons that take up so much of the precious space in my backpack, or having to buy products I’m not used to in foreign countries. A menstrual cup is probably the best thing ever created, especially for travelers.

Hear more from Mallory: Find more about her travels around Peru and how it became her new life on her Facebook page.

My First Time was Exhilarating and Satisfying – A Journey through the Streets of Hong Kong
Laura Nalin | Willful and Wildhearted Laura

As my 26th birthday approached last year, I found myself wanting so desperately to take my first official solo trip abroad as a gift to myself. I sat on my bed scouring the lowest prices I could find on SkyScanner, wondering if I would ever be able to actually follow through with my dream. Sure, I’d moved to Seoul, Korea a few months before that by myself, but I didn’t think it exactly counted. I’d always been surrounded by new friends, coworkers and familiarity in Seoul. I had my own apartment, a steady job and a knowledge of the language, albeit mediocre at the time.

After much internal deliberation, I decided it was my duty to not only treat myself for my birthday, but to continue to literally push myself into new territory. I booked a four day, three night trip to Hong Kong, a country and culture that had always been of interest to me.

A few weeks later, I arrived to the airport bright-eyed and bushy tailed, eager to begin my adventures.

Throughout the plane journey, I felt super proud of myself. A year prior to this trip, I’d been in the most depressed state I can imagine. I mentally high-fived myself, drifting in and out of sleep as I listened to the faint sounds of unfamiliar conversation in the background.

Upon my arrival to Hong Kong, I found my way to the bus station, which eventually led to my hostel. I checked in, read some of my book and fell into a deep sleep, excited for the following day.

Throughout my mini-vacation, I discovered so much about myself and how resilient and capable I am. Sure, Hong Kong has western influence and many people speak English, but I was happy that I was able to navigate the public transportation as well as the city itself by foot without having to ask for help once. I learned that I truly enjoy my own company and I am a great conversationalist with others as well.

I ended the trip feeling gratified and accomplished as well as satisfied to have had the opportunity to drink so much Oolong tea. I’m thankful to have had the experience of a lifetime and though it was a short journey, it is never to be forgotten.

My advice for the first time solo traveler: Allow time for spontaneity. Although I had my schedule pretty packed to the brim, I still allowed down time for myself to chill and meet fellow travelers. By allowing time for the unplanned to happen, your experience will be enriched, as there’s no telling what could happen when you let the universe take hold.

I also recommend keeping extra copies and photos of personal or necessary items with you. This is something I do anyway, but I make sure to do it when alone as I don’t have anyone else with me to fall back on. I always carry a book or my Kindle with me to keep myself occupied when necessary. Most importantly: Have fun! You’re an amazing human who is traveling by themselves – many people are too scared to do what you’re doing.

Something that I always pack that you might not expect [I found this necessary in HK]: The MTR Mobile app. It is truly amazing. It doesn’t require Wi-Fi, which makes it an ideal trip planner. All you have to do is enter the locations you want to get to, and the app will tell you the best way to get there, be it by bus, train or taxi. It’s easy to use and English-friendly.

Hear more from Laura: On her blog, Facebook, Instagram and Twitter.

My First Time was Pushing Boundaries – A US Diagonal Cross-Country Solo Road Trip
Jennifer Melroy | Made All the Difference Jennifer

I was 19 and had was finishing up my freshman year of college. I had accepted a summer job in Mount Rainier National Park, Washington. The job was 3,000 miles from college and 2,500 miles from my home. Time was running out for deciding how to get to Mount Rainier. I looked at my options and made my decision. I was going to drive. I called my mother and I could hear her shaking her head.

A month later, I was off. I was going to National Park hop my way across the United States by myself. I didn’t have a plan for driving until two days before I needed to leave. I also hadn’t considered that half the country was still in winter and snow. I decided that despite this, I would press on and make the drive. I started off on my cross-country drive. The first leg of the trip was easy and the weather was great. Once in Wyoming, I started to get a little concerned. The snow and ice were starting to collect and my little car wasn’t equipped to handle the conditions.

I drove carefully northward towards Grand Tetons National Park, and after a long, sometimes scary, drive I made it. The next day, I went hiking in the snow around Jenny Lake. I slipped and twisted my knee on the hike. I stood there about a mile and a half from my car, knee deep in snow, and by myself. I realized I was on my own and I needed to trust myself. Four hours and a moose later, I made it back to my car. I should have trusted my gut and stopped hiking before I slipped. Yellowstone was uneventful compared to Grand Tetons and I made it to Washington safely.

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My advice for the first time solo traveler: Trust yourself and your gut.

Something that I always pack that you might not expect: I always make sure to take about three feet of duct tape and make a little roll with it. It doesn’t take up much space and doesn’t add any weight. You never know what is going to break but you can always fix it with duct tape. Personal favorite moment was breaking my camera bag strap while out in about in London. Some quick work with duct tape and I was on my way.

Hear more from Jennifer: On her blog and Instagram.

My First Time Was Hectic – A Surf Trip to Nicaragua
Chantae Reden | Chantae Was Here Chantae

Like a good university student, I was browsing flight prices one day in class and discovered that I had just enough money to book a flight to Nicaragua. So, a few minutes later, I did. When my plane landed in Managua, my prearranged taxi driver was nowhere to be seen, leaving me stranded in the middle of the night without any backup plan. I started crying and walked past armed guards to a hotel I could spot from the airport, fending off aggressive taxi drivers as I dragged my surfboard and huge backpack along with me.

The next day, I called a cab to take me six hours to a small surf town that I knew by name and not much else. Of course, the Jeep broke down on one of the dirt roads and people came out of the woodwork in an effort to help us get back on the road. To no avail, we were completely stranded. The driver flagged down three men selling fruit out of the back of their truck and told me to hop in. I helped sell mangoes and apples out of the back of the pickup truck on our way to a well-known tourist town where I could get outside help.

The rest of my trip went off without a hitch, but the lessons I learned from the first 48 hours were invaluable. It’s important to be cautious but it’s just as important to have faith in other people and yourself.

My advice for the first time solo traveler: Don’t wait for the perfect opportunity to travel because it will never come. Staying home will always be more convenient, so stop making excuses and get ready to go now.

Something that I always pack that you might not expect: I always pack a journal, a pen, and tape. I love collecting ticket stubs, notes, and receipts to glue into a book that acts as a free and memorable souvenir. Plus, it helps kill any downtime spent waiting in airports or on long bus rides.

Hear more from Chantae: On her blog and Facebook.

My First Time was Overdue – Tired of Waiting in Chile
Kari Redmond | Words and Other Such Things Kari

If I waited for someone to go with me, I never would have gone. This is what I think about every time I think about my first solo trip. I spent nearly two years living and teaching in Santiago, Chile. The whole time I had plans and dreams to travel the beautiful country and those surrounding it. I would tell fellow teachers who came in and out of my life during my magical time in Chile of my plans, all in the hopes of enticing them to go with me. Many were keen to go. Some even going as far as mapping out itineraries with me. But plans always change. Some went back to their home countries for weddings or funerals. Some took new jobs in other locations. Some found lovers with whom to travel. Some just never got the money together to go. I understood. I did. But I didn’t like it. It meant I had no one to travel with. And for a moment, it meant I wasn’t traveling like I had planned for so long. Then I realized- I could still go. I had the time and the money and the plan. I could travel by myself. This idea had honestly never really occurred to me. I didn’t necessarily think it would be all that fun to go by myself, and of course I was nervous and even a little scared to take on such a big trip, my biggest ever alone or with friends.

But, I decided there was no way I was leaving Chile without seeing as much as I possibly could. I took off on my own for two months south, zigzagging my way through the Carratera Austral, crossing the border back and forth between Chile and Argentina until I reached El Fin Del Mundo, The End of The World, Ushuaia, Argentina. From there I boarded an icebreaker ship with 65 other passengers which took us to the continent of Antarctica where we made landings daily for two weeks.

It is, till this day, the thing I am most proud of- having visited every continent before I turned 28. If I had waited for someone to go with me, I never would have gone. And, I am certain, if I never took that first step so many years ago now, I never would have seen all the other amazing 49 countries I have since visited. Alone.

My advice for the first time solo traveler: If not now, when? Just go.

Something that I always pack that you might not expect: a towel, rum and snacks.

Hear more from Kari: On her blog.

My First Time was On a Whim – Testing the Waters in Panama City
Christina Leigh Morgan | Currently Exploring Christina

For months, I’d been living vicariously through travel blogs, bouncing around within the states every weekend around my PTO, dreaming of the day when I might get out and see the world myself.

As I waited to board the plane, excited, anxious, nervously sipping my stupid Starbucks tea, “I’m doing it…. I’m *really* doing it…!!!” kept racing through my head.

I’d left my job, finally started my own little blog, and was actually on my way — to Panama, where I’d extended a layover on each end of a trip to Aruba to meet a friend. It was my first little baby toe dip into solo travel abroad.

I dug deep for my Spanish to keep conversation on my way into town, booked a last minute Airbnb, got lost in dark alleys, dined solo in Casco Viejo and danced the first night away right until my flight to Aruba the next morning.

On the leg back, I toured the city, played tourist at the Canal, checked into downtown, met an amazing Colombian couple at the poolside bar and danced some more.

Yeah, I could definitely do this. Solo travel was for me.

My advice for the first time solo traveler: Leave your phone in your purse. It can be so tempting to hide in your screen when you’re uncomfortable, tapping away for maps, photos, to-do lists, fervently texting your best friend back home. Resist the urge. Absorb the sights, sounds and people around you with all your energy. Learn to navigate the street signs. Pay particular attention to body language. Pick up a few words of the local language in passing. Once you learn to be comfortable within your surroundings, solo travel is never again alone.

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Something that I always pack that you might not expect is: A Headlamp. Beyond safety, you never know when you might want to throw an impromptu disco party with some new friends (or by yourself)! Enter: strobe feature.

Hear more from Christina: Christina is now a full-time travel blogger and freelance digital strategist. Hear more from her adventures around the interweb on her blog and Instagram.

My First Time was Lonely – In Asia’s Concrete Jungle
Shane Prather | Sea Salt Secrets Shane

Last month, I took my first solo trip. I chose a simple country to test the waters, as I had heard that Singapore was culturally similar to America and the majority of people spoke English. I honestly didn’t prepare myself for a big cultural shock.

Within my 3 short days in Singapore, I was fined $1000 for chewing gum and got told by a local that I’d better toss out my coffee I was sipping because food and drink is banned on the trains. Cocktails were $27 as alcohol is highly regulated with a “sin tax”… but I just had to indulge in a legendary Singapore Sling. I wasn’t in Sydney…or America anymore.

People viewed me as an outsider, and I could see and feel it with every step I took. My mistake was staying in an Airbnb in a single room. Perhaps if I had stayed in a hostel, I could have bonded with fellow travelers and enjoyed myself more.

The highlight of my trip was an authentic meal with a Singapore family I found through Eat with Locals. If you are ever traveling solo, i would highly recommend it. I paid $17 for a one-of-a-kind experience and got a true taste of Singapore culture!

All in all my Singapore stint  was an eye-opening experience, but one that helped me realize, I am just not cut out for solo travel at this point in my life!

My advice for the first time solo traveler: The reality of solo travel, especially for extroverts such as myself who thrive off of human interaction is that you will get lonely. Missed flights, illness and other things will be magnified. In the end, you will come out of the experience stronger than ever before!

Something that I always pack that you might not expect is: A good lipstick. You never know when the occasion may arise to look prim and proper.

Hear more from Shane: On her blog, Facebook, Instagram and Twitter.

My First Time Was Unplanned – A Drive South of the Border
Jessica Elliott | How Dare She10345833_10104041202205281_2554664458951834822_n

Living in Arizona, you have easy access to all that’s around you – beaches in California, fun in Las Vegas, and all that is Mexico. I had changed jobs by freshman year of college and had a few days off between finishing one and starting the other. By some miracle, I also didn’t have classes. So what’s an 18 year old girl to do? I decided that I was going to drive south until I hit the water. I ran my finger down the map until I saw blue; I was going to Guaymas, Mexico. And that’s about as far as my planning went. I spoke Spanish, I had been to Mexico a dozen times with family and church, and this was before Americans needed a passport to go, so I grabbed a few clothes, a water, and a shockingly small amount of snacks and hopped in my Jeep.

This would not only be my introduction to traveling by myself, but also to the dumb-foundedness of others trying to understand it. At the US-Mexico border:

“Where are you heading?”

“To Guaymas.”

“To see your boyfriend?”





“No sir, just driving south. I want to go to the water.”

“By yourself?”

“Yes, sir.”

“Not with anyone else?” [um, didn’t the last question cover this?]

“Correct sir.”

“So you’re by yourself, not going to see anyone or with anyone? That’s strange.” He handed back my ID.

“Thank you sir.” And I drove on.

This conversation would be repeated in almost precise replication at the Sonoran border heading South, then back North, and again at the US-Mexico border crossing back into the States (and subsequently all future solo trips). All in all, it was an uneventful trip and I spent more time driving than being there. I got to “the water” I was after and it certainly was no beach. Maybe that’s where a little more planning would have come in handy. But I “camped” locked in the Jeep overnight in a parking lot near the water anyhow. I drove around a bit in the morning, gassed up and headed back home. I realize now I don’t think I ever told my mom. Always tell your mom.

My advice for the first time solo traveler: Fully acknowledge that something will go “wrong”, or not to plan. Be prepared to be flexible and you’ll better absorb whatever may come your way. And don’t get thrown off by it. Just like in our day-to-day lives things go differently than we expect, and it’s how we react that makes the difference.

Something that I always pack that you might not expect is: a scarf. Even when traveling to hot places. A scarf can be really versatile if you make sure it’s big enough. It will be a sarong, a pillow, a blanket, a shawl, tied up into a tote for groceries – I’ve even used it as a table cloth when trying to play cards on a slippery table on a train.

Hear more from Jessica: Here! Or check out How Dare She on Facebook, Instagram and Twitter.

Do you have a first time story to share? Or getting ready for your first trip! Share in the comments or you can send them in. Stories submitted will be compiled for a future roundup in this series.




Founder of How Dare She, Jessica is on a mission to visit every country in the world, and bring you along with through photos, video and stories. 6 continents and 104 countries in. She has a BA in journalism and Master's in innovation and change, but her real skill is plugging in a USB in 2 or less tries (most of the time). She believes daring isn't about being fearless, but choosing to opt in, in spite of fear. She dares to see, taste, experience and meet the world as she goes.

2 Comments on “My First Time Was…

September 7, 2015 at 9:54 pm

Great post! The first time is both the worst and the best, its terrifying because you’re finally doing something you’ve dreamed off, but you’ve said goodbye to everything familiar to do it. It’s great to see how other solo female travellers found it, and brilliant that they’ve all been inspired to keep traveling 🙂

christina @ currentlyexploring
September 9, 2015 at 9:30 am

love these stories! so fun and inspirational to think back about “the first” 😀

xo christina


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