My Romantic Trip to Italy Alone and What I Learned


I was 29 years old and had been single for 2 years and I was freaking out about turning 30 in 4 months. The expectation when I was younger was not to be single and living in a basement suite when I was 30. I felt awful about my life situation and embarrassed that this was where I was. I felt like a complete failure at life and love and was super depressed about the whole thing.


However, I also happened to be learning about myself a great deal at this point in my life and was learning how to love my own company and the importance of getting out of my comfort zone. I decided that 30 year olds do not wallow in their basement suites waiting to be rescued and this also wasn’t a very attractive way to live either. I began thinking of things I could do for myself that I’ve always wanted to do but had put off until I found a boyfriend.

One of the major things I had always dreamed about was travelling to Italy. I had seen photos and talked to people who had visited and I wanted to go soooooo badly! But I held off because Italy was a place of romance, and lovers and good food and wine. That was something I always imagined sharing with a romantic partner.

With my 30th birthday quickly approaching though, I decided to say screw it and book a trip. It was my birthday present to myself and I was going to go to Italy, with or without a person to share it with. I got in touch with a travel agent and booked myself 3 weeks in Italy by myself and I was scared. Don’t get me wrong, I was excited, but I was mostly anxious. I had never been overseas before, let alone by myself, and I was terrified of flying. I hated it. But I was also sick and tired of putting my life on hold, so I booked the trip and started planning.

I had my first 9 days booked with a tour group so that I could get used to being on my own and get to know how things worked over there. The tour group was amazing and I really enjoyed meeting people from all over the world. I was having fun, but also extremely anxious about the following two weeks on my own. I had planned to stay in Cinque Terre for 5 days on my own after leaving the group, and then I would need to get myself down to the Amalfi Coast for another 6 days. I had so many self-doubts and anxiety about the whole thing that at times I couldn’t even enjoy what I was doing.

I knew that trip was going to be life-changing for me though. I had to prove to myself that I could do this, I could travel on my own, get myself around and do the things that were really important to me without being dependent on having someone else I my life to do them.

I took the train over to Cinque Terre where I spent 5 amazing days hiking between the 5 stunning villages along the coast. I swam in the Mediterranean Sea every day which had been one of my dreams for so long. I ate my face off, had dessert after every meal and took in the beautiful scenery. Then I headed down to the Amalfi Coast where I spent another 6 days on my own eating breakfast, lunch and dinner by alone, which was a big deal! I wasn’t meeting a lot of people because I was staying in bed and breakfasts rather than hostiles and I remember feeling very lonely often but also so grateful that I had done this for myself and for the experience.

My three weeks in Italy taught me a lot. I learned to have so much more faith in myself. I gained self-confidence and awareness around my feelings about being alone. I proved to myself that I didn’t need to put my life on hold because I was single and that it was very important to do these things for me. I saw how beneficial it was for me to love my life now, rather than wait to love it until I had my soulmate. I may have been waiting a long time and I was through waiting around for my life to start.

It turns out loving your own life no matter what your relationship status is makes you quite attractive! I learned this also while on that trip and have remembered that ever since. I felt amazing and this energy radiated out into the world. That trip was totally life-changing and I would recommend it to anyone, but you don’t have to go to Italy to learn the same things. You can begin right now loving your life. Take yourself out on dates, go to that new restaurant you’ve always wanted to try, take those dance classes, or art classes and build a life you love. You’re totally worth it.

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