Happy Women Who Wander Wednesday! I’ve made the decision to post these weekly on a Wednesday (for now anyway) due to the amount of submissions I have received over the past couple of months! Again, thank you all for your interest in this series, it’s so inspiring to read all the incredible solo female stories you are sharing! This week Amy talks about finding her strength in solo travel

Meet Amy

strength in solo travel

My name is Amy. After taking a couple of pre-planned tours and realizing that my favorite part of those experiences was going off on my own and getting lost in a city, I decided my days of conventional travel were behind me. With that as inspiration, I booked my first solo trip to Cuba, much to my friends’ and family’s horror. But c’est la vie! If I hadn’t had the travel bug before, I certainly do now. For now, I’m parked in my home state of Florida while I save up for a loosely defined plan to move out of the country, location to be determined. You can follow my (sometimes mis)adventures on my blog, Travel Outside the Lines, which strives to embrace and encourage non-conformity and unconventional travel.

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The Strength in Solo Travel

“You’re going where!?”

If I had a nickel for every time someone uttered that response when I described my trip to Cuba, I could have funded the entire trip without ever opening my wallet.

When rumors began floating around that US-Cuban relations were warming and that travel restrictions may be lifted, I knew I had to jump on the opportunity to visit (1) before either government changed its mind, and (2) before Americans ruined Cuba for good. I wanted to see Cuba as it was, before Venti Mocha Frapa-machi-whatever-os and the big Golden Arches invaded.

“You’re going with a tour group, right?” No. “Well, with friends, then.” Still no. “You’re going by yourself?” Ding, ding, ding! We have a winner!

strength in solo travel

Now, I don’t consider myself a seasoned world traveler by any stretch of the imagination. To this point, I had only been to 5 other countries outside the US (including Mexico with my parents when I was 8), and I had never traveled internationally by myself.

What better way to break into solo travel than to visit a country that was not necessarily favorable to Americans, where my US-issued debit and credit cards would be non-functional and I couldn’t be wired money if I got stuck, and where I did not speak the language, for 2 weeks all by myself? Oh, did I mention I also planned a trip that had me covering nearly 1,200 miles and 7 cities from Santiago to Viñales?

Working Up to Solo Travel

“Are you crazy!?” (An alarming number of people asked me this question.) And the answer is, quite possibly.

In all fairness, I did work my way up to solo travel over the years. My first adult trip abroad was in college as part of my Honors World Lit class. We were studying French literature that year and it came with a week-long trip to Paris with 51 of my closest friends and professors. A couple of years later, I booked a trip through the same tour company to Italy and Greece. It was a group tour, but I didn’t know anybody prior to going (as opposed to some people who went with friends). Naturally, this trip to Cuba was the next step (leap), right?

And while I might very well have lost my marbles, nothing about this trip really concerned me. I didn’t even buy a travel guidebook. That alone should have been a red flag. I should add that I am also, by no means, fearless. Maybe I was so excited I blocked out the nerves. More likely, I was just too consumed with my day-to-day to really notice. Honestly, I’ve never felt so unprepared for a trip in my life.

Unprepared or Just Going with The Flow?

Normally, I’m so over the moon about any upcoming trip that I’ve started packing a week in advance and have been researching things to do for months, detailing every minute of every day of my itinerary.

That was not the case for Cuba. I did some basic research to decide what cities I wanted to visit, but I mostly relied on recommendations from a friend who grew up there. I booked my accommodations and my local transportation, because I am not yet one of those travelers that feels comfortable just showing up in a city and hoping it will all work out.Knowing how I’m getting from Point A to Point B and where I’m laying my head at the end of the day is important to me. But beyond travel and accommodations, I did no planning. Remember, I didn’t even buy a guidebook.

I also thought I knew enough Spanish to get by. I found out just how wrong I was as soon as my flight landed in Santiago. To be honest, I was amazed that I managed to make it to my first host’s casa without getting killed. Luckily for me, girl carrying suitcase is a pretty universal sign for “I’m lost and need a taxi.”

Nothing is Going to Stop Me Travelling

The one question I hear most often is whether or not I was scared to travel by myself, especially to a country like Cuba. Here’s the thing: I want to travel. I want to travel a lot. And it is very unlikely that friends and family will be available to travel when I want, where I want, and how I want. And since giving up travel is definitely not going to happen, I decided that I’m just gonna go. I’m going to buy the flight and book the trip, and if somebody wants to come with me, great. But if they don’t, I’m not going to let that inhibit my travels.

strength in solo travel

Solo travel, for me, is about seizing the moment. I never would have gone on this trip had I waited for somebody that wanted to go with me. Most people were and are concerned about traveling to Cuba. Those feelings are completely valid. I spent a lot of time wandering around like a lost puppy, trying to decipher a language I didn’t understand, and being totally and completely out of my comfort zone. That doesn’t appeal to everyone. And a healthy fear of anyplace unfamiliar is, in my opinion, a good thing. Respect your environment. Be aware of your surroundings.

That being said, this was the most incredible experience of my life and I wouldn’t trade it for the world. While I may have struggled to overcome a lot of obstacles, I also found my strength in solo travel and learned how capable I can be should the need arise.

I picked up quite a bit of Spanish during my travels. I kind of had to. Trying to have a conversation took a lot of effort. I had to think hard to have a simple exchange. That wasn’t a bad thing. It was just exhausting. The struggle of immersion was exactly what I was looking for. And I guess it worked, because halfway through my trip, I was having conversations seamlessly enough to fool some Spanish-speakers that I knew what I was saying.

The Beauty of Solo Travel

strength in solo travel

I met beautiful, genuine, authentic people, both Cubans and fellow travelers. These may not be people who I will keep in touch with forever, or that I’ll even see again, but believe that the people you meet in your travels are the best friends you will ever make, even if you’re only friends for a few hours.

Something to keep in mind, too, is that Cuba is a very safe country to travel in. I visited seven cities across the country, and the only one where I felt wary (beyond the general and healthy anxiety that comes with being in a new place) was in Havana. Havana is just like any other big city. There are neighborhoods where you don’t want to be caught after dark. There are strangers and con artists trying to take advantage of you. This is something you will experience everywhere.

Admittedly, I am also not a big city person, so that type of environment makes me uneasy. I was much more at home in the smaller, more rural areas of Cuba. In Santiago and Trinidad, for example, I had no problems whatsoever walking around by myself at night. I kept my belongings close and was on high alert (and people probably looked at me like I was insane).

Major crime isn’t a thing in Cuba. I suppose that’s the one benefit of a strict communist regime. Crime is very heavily punished there, so the risk isn’t worth the reward. The most dangerous thing you’re likely to experience as a solo female traveler is Cuban men catcalling you and trying to pick you up, which is really more amusing than harmful.

Find Your Own Strength

I think solo travel is something everyone, especially women, should experience at least once in their lives. You will find your strength as a person, you will realize just how independent you are and you are likely to fall into opportunities and experiences that you may not have with a group. You will be able to do the things you want to do, without compromise and without feeling guilty about it and you will meet friends along the way. My advice is also to allow yourself to be swept up in the moment and to be spontaneous. Allow yourself flexibility in your plans. Allow yourself to fall in love with the culture and soul of the country. You will never regret it. And don’t be afraid of adventure. It’s waiting just for you.

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Finally, If you are interested in writing for Women Who Wander, you can contact me at youngandundecidedblog@gmail.com. Can’t wait to share your stories

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10 thoughts on “Women Who Wander: The Strength in Solo Travel”

  1. So many truth in those words… Solo traveling is not for everyone (I personally didn’t like it), so I really admire women who got the guts to do it.

  2. Solo travel is such an incredible feeling, I wish that everyone got to experience that feeling. Although so people do not like it, you should try it at least once in your life.

  3. This was such an interesting read. I’m currently planning my first solo trip which will be to America for 10 weeks from the UK so I’m fully going in the deep end. My first three weeks will be with a tour but I’m really looking forward to being able to travel on my own terms and explore where I want to go. I’ve had so many comments saying I must be crazy to be going by myself! xo

  4. Amy, I can totally relate! I am a solo traveler and I luv it. I enjoy the freedom and flexibility. There is no better way to learn more about yourself and the world. By exploring on your own terms, you become more open-minded. Cheers to continued growth and new adventures!

  5. I am sad to say that I have yet to travel solo… but after reading this I absolutely can’t wait to get started! It really must be an empowering feeling.


  6. Love this!! I also get so many comments when I book trips to take by myself, I’ve learned to take them in stride. While it isn’t for everyone, we don’t go around gasping at others and saying “I can’t believe you’re going with your SO!” 🙂

  7. I get comments about solo travel too, but I think it’s a necessary thing that everyone should do once in their lives. Also I would love to go to Cuba!

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