It was a devastating moment. Four days before we were set to leave for Italy, my 18-year-old niece had to back out of a trip that I had been planning for nearly a year as her graduation gift.
It was so last-minute that trying to find anyone to take her spot was impossible.
The financial implications of not going were manageable — almost everything had a decent cancellation policy built in — but the emotional implications of not doing all the things I had been dreaming about, as well as researching and plotting, were cruel.
At the Cantina del Vesuvio outside of Pompeii, Italy. A selfie stick was a necessary packing tool for a recent solo trip to Italy.
What was I going to do? It wasn’t going to be sitting at home and moping for two weeks, that was for sure. I took in the big picture and decided I’d be taking this trip by myself.
When I told my family and friends, most were incredibly supportive and positive. Of course, there were a few doubters. I listened to my cheerleaders, and I knew that I could do this — a decision that led to one of the best trips I’ve taken.
Imagine taking a trip where you get to do everything you wanted, don't have to wait on people and have the opportunity to enjoy yourself without worrying if someone else is also having fun. This was that trip.
Accomplishing this required a few leaps of faith, some trust in the universe and strangers, and confidence in myself.
Safety
I knew I had reasonable travel plans. Italy is incredibly welcoming to tourists. Months of planning made plotting out the trip easy. I had already ensured that the Airbnbs and hotels I booked were well-reviewed and in safe areas. Being aware of my surroundings was important.
I probably kept my head on a swivel a little more than I usually would and kept my purse closer. I updated my husband with a daily itinerary. There are also plenty of apps that can share your immediate location with a loved one 24/7.
A solo seat at a restaurant in Florence means dining by candlelight next to a big fridge of meat on display.
Reframing ‘pity’ moments
In Rome, on the third morning of my trip, I woke up a little lonely and sad. I hyped myself up and got moving, determined to make the best of the day. I walked to a few sights and came across a secluded lunch spot. I thought about how I had been enjoying the planning of this trip, and now I was executing those plans, and how lucky I was to be there. At that moment, the best lasagna of my life was placed in front of me.
After a few bites, I realized there was not a single thing I had to be sad about. I ended up having an incredibly enjoyable day.
Trust
From Rome on the way to Sorrento, the second stop of my trip, I previously hired a driver/tour guide to stop along the way in Pompeii. After the rush and bustle of Rome, I was looking forward to the more laid-back vibe of Sorrento and decided to ditch Pompeii that morning.
When I met my driver and mentioned this, the driver had a friend who owned a winery where I could get a tour, get scenic views and have lunch, and did I want to do that instead? Yes, please! And on the way, did I want a couple of great photo opportunities and a stop at a limoncello factory before the hotel? Um, sì!
A little photo opp in a Fiat outside the DiCapri limoncello factory and store along the Sorrento peninsula in Italy.
Could he have taken me to an ax murderer’s farm? Maybe. But this leap of faith and reassurance that this was a reputable business really paid off. It was relaxing, fun and exactly what I needed on the next leg of my trip.
Craving conversation
While I was enjoying my solitude, I did crave conversation. Booking smaller tours and excursions made it easy to strike up a conversation with a stranger.
I met so many people, and several of them were also solo. Couples or families were looking to talk to someone outside their traveling circle. At the end of my trip, in Florence, I decided to do a food and wine tour, and it was so easy to make friends over a large dinner table. I wish I had done this in every city I had visited.
Joining a small progressive food and wine tour was an easy way to make friends and have conversations.
Other days, it sometimes felt awkward to be eating alone, but I quickly got over it. No one around me cared, and most of the wait staff was welcoming and fun to talk with.
Practicing patience
I had to be patient on this trip. I could only complain about something particularly frustrating to my inner self. If I had had other people I knew around me, I probably would have complained about a line or whatever small annoyance was happening. Instead, I kept it to myself and realized how minor something was.
If I got lost or slightly confused, I simply stopped, regrouped and worked through a situation. I developed a lot more patience with myself as a person.
I also studied and utilized Google Maps, dropping pins all over the place on things someone had mentioned to me, or something I wanted to come back to see if I passed it on the way. It was also helpful if I was headed to a specific place to have the directions pinging precisely to my Apple watch so I wasn’t distracted staring at my phone.
Coming down from the fun of the trip, someone asked me if I had any regrets. And no, there was not a major thing. Next time, I would keep a journal to jog some memories. And maybe, I would also have shortened the trip by a couple of days because I did miss the ones I love.
A suggested change in itinerary led to a scenic drive to Sorrento along the Gulf of Naples, with picturesque views of Mt. Vesuvius.
'Musts' list from a newbie who traveled alone:
- A selfie stick. Get over feeling like a weirdo. You want a cool pic of yourself and you can stage it that way and not worry about someone running off with your phone.
- Decide on your must-sees and plot them out ahead of time.
- Group tours. The best conversations I had were in smaller group tours.
- Trust in the randomness of things, and trust your instincts.
- Get over yourself. You don’t know a single person where you are going. No one is paying attention to you and wondering why you are alone. This is especially true with meals.
- Avoid overpacking. There isn’t anyone able to watch your luggage if you need to dart off to the bathroom in the airport. Keep it simple.