Italy Solo Female Travel

What 3 Months Traveling Solo in Italy Taught Me About Pleasure, Patience and Saying Yes

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Traveling solo in Italy for 3 months taught me so much, but how did I get that idea, and where did I find the time? From the time I boarded a plane to Spain to study abroad as a college Junior, to two months ago when I came home from a solo trip to Japan, I’ve found solo travel to be exciting, enlightening, and eye-opening. But once I got past university and entered the ‘real world,’ finding time to travel became harder. There were years I didn’t travel at all (a travesty!), and others where I made it a priority. But the trips were brief, the time was amazing but too quickly I was absorbed back into day-to-day life.

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Three Months Out of One Bag is the Goal

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The Catalyst

Until 2018. 2018 became a year of transformation, exploration and adventure. I know I know, that sounds so evolved and high-minded, as if I spent this year on one magical journey. It was a journey to be sure, but it wasn’t always magical or adventurous. You see, in January of that year I was laid off. Being in business for over fifteen years and seeing this happen to so many I know and love, I’m surprised I made it that far with it only happening once. But happen it did.

And can I tell you? While there was fear of the unknown, humiliation and a sense of failure, there was also something else. Relief. The culture that I tried so hard to fit into, the politics and behaviors that ran rampant, I could finally leave it all behind. I had been ready to leave for some time but was waiting for the perfect thing. That thing that felt right. And while several opportunities came along, they never checked all the boxes. So now here I was. The universe was giving me the kick in the arse I needed to get out there and figure it out on my own. So now what?

For so long I had fantasized about quitting the corporate world and traveling for a year. Thought about how I could transition to a fully remote job so that I could be anywhere in the world and still have a steady career. Travel has been and continues to be one of my passions, so finding a way to blend that with an income has been top of mind. Opening a B&B in Tuscany. Buying rental properties in Sardegna. Designing trips of a lifetime for people that didn’t want to/have time to to/know how to do it themselves.

The Plan – Or Lack Thereof

So, with all these thoughts permeating around in my brain I thought, it’s now or never. Yes, I could jump back into the next corporate job, and in fact had an offer to work at a great company the week after I left. But it was too soon. Too much to think about, too much to do. You see, I was given a gift. The gift of time, the gift of freedom, the gift to release from everything that I’ve known to figure out what I truly wanted to be. And you can bet I accepted it graciously.

So, what came first? I’m a planner by nature, so of course list-making made a big appearance. Lists of places to go. Lists of careers I could have. Lists of must-haves in a role. And lists of things I wanted to accomplish. I was ready to take time off but still wanted to have a sense of purpose. That was one thing I wasn’t quite ready to let go of. And so little by little, I laid out options. Part plan, part fate, and part intuition, my year took shape. And one part of that year included a 3-month solo trip through Italy, visiting cities I hadn’t spent time in on my prior trips. Starting from the south in Sicily, and ending in the mountains around Mont Blanc, it was a summer of self-discovery, letting go, and finding my light again. So, what did I learn during my solo adventures?

1. You’re Braver Than You Think

Traveling alone can seem daunting at best, lonely at worst – both of which can create angst. From boarding that first flight, having that first dinner solo, and making your way through a bustling city, it’s natural to have some anxiety or self-consciousness about doing it alone. For me, those moments no longer induce fear – they create an open portal of freedom. But that happened over time.

Each time I did it, I realized it wasn’t as bad as I thought – in fact, it was kind of great! As I let the discomfort settle in, I learned that it could then dissipate. These micro-moments happen throughout a trip. I remember boarding a sailboat for a day trip in Sardegna, and the only other passengers were all Italian. It was quite intimidating at first, but it became a good way to practice my Italian and meet locals to the country I was visiting. In these moments, I didn’t see it as bravery, but in hindsight it was. You can then take this bravery and apply it to other situations in life, having a bit more confidence in your ability to handle anything that comes your way. 

2. Strangers are Kinder than You Expect

Once I boarded that boat, intimidated by my remedial Italian and fear of how to communicate or whether anyone would WANT to communicate, I was quickly proven wrong. The other passengers kindly embraced me, and we had a great time on the water that day.

Luckily, this wasn’t a rare occurrence. Everywhere I went, people struck up conversations, were helpful in giving recommendations or directions, and never hesitated in lending a hand. My bed and breakfast hostess in Cortona who kindly called the rental car company for me to confirm where I should return it. The Airbnb hostess who called her friend to take me to a secret grotto in Santa Teresa. The gas station attendance somewhere between Naples and Rome who confirmed I was headed indeed in the right direction. Everywhere I turned, I saw kindness. It helps you restore faith in humanity and realize this kindness exists at home too, you just have to be open to seeing it.

3. Planning Less Opens More Doors

As I mentioned, I’m typically a planner. But for this trip, I chose to be a little more carefree. To push my boundaries and be open to anything that may come my way. Wanting to travel a little slower, I spent between a week and a month in each stop. I determined my next destination about a week or two before I left.

This let me lean into my intuition and see what I was really interested in doing, where I was interested in going. In some cases, places that were high on my list fell by the wayside in the moment, while other new ones popped up. This also allowed for some impromptu opportunities – meeting up with a friend of a friend in Torino; reconnecting in Naples with people I met earlier in Sicily, and having newfound friends in Tuscany take me on day tours of a city. While it’s nice to have a plan, there’s a sense of freedom and spontaneity that comes without one.

4. Loneliness Isn’t the Enemy (Boredom Is)

One concern many people have about traveling solo is being lonely or not having someone to share the memories with. While both are valid, it’s not a bad thing to spend some time alone. For me, that was time for self-reflection and enjoying the moment. When you’re traveling, there’s also so much to see and do, that loneliness doesn’t set in as much. Now, if I stayed in my flat and never did anything, I would have gotten bored, and that would have been lackluster. Don’t get me wrong, I needed some down days to do laundry or just enjoy a relaxing day in, and I let myself have them. But I also balanced those with days wandering through my new town, and sprinkling in weeks of hiking through Amalfi, Tuscany and around Mont Blanc. Embrace the alone time and let yourself enjoy the adventure – you deserve it!

5. You Learn to Trust Yourself Completely

As you’re doing these things alone, there’s no one to bounce ideas off of, no one to defer decisions to, no one to fall back on if something goes astray. This can be stressful at first, but you learn it’s really not that serious, and you learn to trust yourself. It builds your confidence in making decisions, flexing when needed, trusting your gut on what you want to do and where you want to go. That is freeing and is a skill that applies to other things in your life when you return home.

6. You Discover What You Really Like – and What You Don’t

This also gives you the space to realize what you like and what you don’t like in your home life. Whether that’s a job, a relationship, or a location you’re living, having a break from your day-to-day allows you to really assess things from a fresh perspective.

For me, I realized I really did enjoy what I did in my career, but I didn’t think where I was living was meant for me long term. I actually started doing consulting work while I was on the road and loved it! That clarity may have come if I had stayed home or traveled with other people, but I believe it comes faster and clearer when you’re solo and have time to really give it some thought. This also helped me solidify my priorities in life. Spending time with the people I love, continuing to make time for travel, and staying healthy were imperative for me to maintain when I returned home.

7. Connection Is Universal

Back to the loneliness aspect, I did miss friends and family back home – especially being gone for three months. What helped with this is realizing that the craving for human connection is universal. It was fantastic to meet other travelers who became fast friends. It helped spending time in a couple of language schools, as well as joining some group hiking trips, where you could spend more time with people and build a bit of a deeper bond than the one I had with my friendly baker who I saw each morning. Some of those people ended up becoming close friends that I met up with later in my trip. While nothing replaces lifelong friends or family, they were definitely wonderful humans who were kind, open and who I can call friends to this day.

8. Home Will Feel Different When You Return

The pinnacle of my trip was hiking around Mont Blanc before returning home. I was nervous before the trip, but it was amazing and a fantastic way to end my stay. After three months traveling, it was bittersweet to return home. I craved more adventure, but I was ready to return to the people I loved.

When I return from a trip, I always tell myself my new habits will stay in place. I’ll walk 3-5 miles a day, I’ll make my lunch and dinner fresh each day, I’ll have wine with every meal. Well, I can say I got closest on the wine bit, but the other things fell away as I slipped back into our US routines. But that doesn’t mean things don’t feel different. You have a wider perspective on life, on different cultures and people. You have more confidence and patience. You’ve had experiences and memories that only you have, like a little secret that you get to keep and cherish for years to come. You not only survived, but you thrived. And if you can do that, you can do anything. The only question is, where to next?

Conclusion

Whether or not you decide to travel solo, hopefully this gives you a sense for what to expect, and things you could potentially learn about yourself and humanity. Taking 3 months off may not make sense for everyone, but even a few days or a week can do wonders. While daunting at first, these lessons are some of the things that keep drawing me back time and time again!

Interested in taking the plunge and traveling solo, but still not sure on how to get started? Contact me for custom trip planning guidance!

Wherever you go, however you do it, I want you to have a trip to remember.

Happy travels, kindreds!

Ready to Plan Your Solo Adventure?

There are two ways to keep going from here. If you want the full playbook on traveling solo as a woman, start with my Solo Female Travel guide, it’s everything I wish I’d known before my first trip alone.

And if you’re ready to go but want someone to handle the where, the how, and the details while you sit back and relax, that’s what I do. I’d love to help you plan your next solo getaway.

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