The Unfiltered Truth About Traveling Alone

I posted about my trip to the Amalfi Coast recently and one aspect of the trip that I didn’t go into much detail about was the fact that I was completely alone there. And it was my first time traveling alone! Scary.

I wanted to save this topic for an entire post to give some feedback for those of you that might be considering traveling alone, but aren’t sure exactly how it’ll pan out.

Travel blogger traveling alone in Positano, Amalfi Coast, Italy.

You will be SO nervous.

Yes, traveling alone changes you. It helps you find yourself. But the truth is, the night before I was supposed to leave, I was laying in bed talking to Austin and I was almost in tears saying:

“I don’t want to go. This is a mistake. I just want to stay home.”

To be honest, I knew this would happen. My gut reaction every time I do something big like this is to just not do it. I’d rather cancel everything and forget I even had the idea in the first place.

Don’t do this. Push through this mental barrier.

Things WILL go wrong.

I know this. I know you know this. Things always go wrong. Something always happens to throw a wrench in the plans you thought were perfect. Ever heard of Murphy’s Law?

However, I still tried to plan my trip as perfectly as possible – starting with my travel to Italy. I planned everything so precisely so that nothing would go wrong on the way there, and I wouldn’t get even more discouraged than I already was.

Specifically, I took a cab to the airport (instead of the blue line subway) in Chicago. I flew to London and booked a lounge for my 6 hour layover (instead of dealing with noisy, rude airport people). Then, after flying to Naples, I had booked a private driver for my transfer from Naples to Positano (instead of a train + bus combo).

Luckily, everything went smoothly on my way to Positano, BUT I never accounted for the fact that my iPhone would completely shut down and stop working.

Not everything worked out

That’s right – on my second full day in Italy, I was left with no phone and no reachable Apple store.

Now, I could have brought an extra phone with me (my dad does this, I probably never will), but the point I’m trying to make here is that no matter how much you prepare, you will never think of everything. And usually, the thing you don’t think of will be the thing that goes wrong.

When this happens, all you can do is figure out what you have control over. You should try with everything you have not to stress about “why did this happen to me?” or “now all my beautiful pictures are gone!”

By the way, I’m not perfect in any sense – I stressed a LOT. I called (Skyped) Austin crying about 18 times.

But after I had my pity party, I started to think:

What can I control? How can I help the situation?

This stage is when I asked the hotel (in Italian, I might add) to use their printer to print my train ticket to Rome. I also asked for a map to the nearest Apple store so I could just hand that to a taxi driver when I got to Rome.

At this point I was feeling a little better because I was spending my energy on fixing the problem instead of dwelling on my bad luck.

To make matters even worse (now I’m dwelling again), when I did try to hand the map to the Apple store to the cab driver, he had no idea what I was talking about. Since I don’t speak Italian, I just had him drive me to my hotel. This is where I was meeting up with a group for a group trip across Italy.

Now, I’m at the hotel…

I tried to check into the hotel and my name wasn’t in their system. I guess the hotel was changed last minute, but no one could get a hold of me for obvious reasons.

Then, the hotel desk associate asked me if there was any information on my phone I could show him to try and fix the matter. I broke into hysterical tears and I feel so bad for that man. I tried to explain why I was being a crazy person, but he was so nice and understanding. He just tried to get me to drink some tea and calm down.

Long story short, I found my group at our actual hotel and one of the trip trip managers that spoke Italian came with me to get my phone fixed.

Travel blogger traveling alone in Positano, Amalfi Coast, Italy.
A tripod is a solo traveler’s best friend.

OTHER people are weird about YOUR choices.

I think of myself as a relatively independent person. I don’t get awkward or uncomfortable when going to dinner alone, or sight seeing alone, or striking up conversations along the way, but other people did.

Remembering back, there was a restaurant on the beach in Positano that a lot of travel bloggers recommended. They also said it would be wise to make a reservation because it fills up quickly. So, one night I called them and asked to make a reservation for the following night and they said “okay for two people?” and I said, “well, no. It’s actually just one,” and the woman laughed and said “just you?”

And I hung up.

As simple as her statement was, it really stung. It’s already such a romantic town that I wished Austin was with me, or even a few friends. I didn’t exactly want to be reminded that I was alone when I was already feeling somewhat lonely.

Dealing with others’ responses

Similarly, every time I mentioned my trip to Italy before I went, the first question was always “are you going with your boyfriend?” “No..” I’d say, “by myself.”

Their eyes almost automatically went wide and they’d ask why he wasn’t going, if things were okay between us. “Of course! He just couldn’t fit this trip into his schedule.” “So you’re going ALONE?” As if that would be the worst possible situation. They almost felt bad for me.

Now, of course this wasn’t everyone. I also got a lot of very supportive “good for you!” responses, but the look of pity that some people gave me almost made ME feel sorry for THEM because their insecurities of traveling alone were very clear.

This is how you should approach negative responses. Be so confident in your decision that it causes other people to think “hmm, maybe I could do this.”

You will only have to think about YOURSELF

I am very much a people-pleaser. My therapist and I came to this conclusion many moons ago. So, it was so WEIRD to only think about myself.

What did I want to eat? What did I want to see/do? How was I feeling at any particular moment? Tired? Take a nap. Hungry? Eat. I think most people are so conditioned to take others’ thoughts and feelings into consideration (which is a good thing), that we sometimes put aside our own basic needs.

I actually recall one specific day – the day I went to Capri.

After exploring Capri in the rain and then heading back to Positano, I was soaking wet and extremely tired. So, I went to take a nap. But there was so much more that went into that.

To give some back story, I tend have a (seemingly) common mindset when I travel:

I will never be back here, so I need to see and do everything, or I’ll regret it for the rest of my life.

I didn’t ever want to nap or sleep a full night, or do anything that wasn’t incredibly exciting. But getting of that boat, I was drained and I was actually feeling very lonely – like overwhelmingly lonely.

What helped when I was feeling lonely

I ended up Googling “what to do when you feel lonely traveling alone” and got some of the best advice I could have read. Indiana Jo, I can’t thank you enough for your advice:


If you’re feeling especially lonely, you’re probably also tired or hungry or thirsty. Those feelings are snowballing to bigger ones causing you to second guess your solo travel in the first place.

I took a step back and realized, I’m literally sopping wet, I’m exhausted from lack of sleep and walking so much, and I could definitely eat.

That’s when I decided to take a nap, and BOY did it help. I woke up refreshed and ready to head to dinner. After dinner is when my phone broke which brought on a whole new set of problems, but one step at a time, people!

Lemon Sorbet in Positano, Amalfi Coast, Italy.
Thinking about yourself = eating as much lemon sorbetto as your heart desires

You’ll be THANKFUL you did it

I don’t regret starting my trip early by myself one bit. Through all the events I described above, I proved to myself that I can adapt, I can think for myself, and I can live and act with myself in mind.

Like I mentioned, I’m a huge people pleaser. So, living solely for myself for even three days was way outside of my nature, but it was so freeing!

I know a lot of people who absolutely love traveling alone. They love meeting new people and they love the serenity. For that reason, once they travel alone, they want to do it again and again. Maybe that’ll be me!

Have any of you ever traveled alone? Tell me how it went!

Love this post? Pin it!

Leave a Comment