I am literally traveling in circles, I conclude to myself as I come across the Fontana dei Quattro Fiumi statue for the fourth time. As beautiful as it is, this was my starting point thirty minutes ago. After enjoying a lovely traditional Roman dinner of spaghetti a cacio e pepe, I casually traipsed around the Piazza Navona before realizing that it was almost midnight and deciding that I better make my way back to the B&B across town.

I’m feeling pretty low at this point. Worried that I might have a breakdown if my next attempt at finding the main road unsuccessfully culminates back at the Piazza, I do an internal ‘I told you so’; how could I possibly think that I could travel to a large, foreign city alone when I get lost, quite frequently, in my own neighbourhood. I eventually made it out on my fifth attempt and was pleasantly surprised when I managed to navigate the local buses like a pro back to my B&B.

When I was living in Germany, I had a few weeks off and wanted to finally make it over to Italy, but I couldn’t find a travel buddy who was able to tag along. I never envisioned myself actually traveling alone. As is clearly demonstrated above, I am directionally challenged with an added mix of social awkwardness. So overall, completely incongruent with the qualities I associated with people who travel solo.

Here are some insights that I’ve gained from this experience that I hope will be of use to anyone out there that decides to travel solo:

Do more planning than you normally would.

The absolute worst thing that could happen when traveling alone is that you put yourself in a less than safe situation because you failed to plan accordingly. Not as bad, but still frustrating, is if your laissez-faire attitude prevents you from working out key details, potentially ruining your trip and causing some ultra unpleasant experiences (for which you have nobody to commiserate with).

A classic example that I have often heard from people who frequently travel solo: deciding to wait until you arrive in your destination to find lodging because you are so ‘spur of the moment’, without realizing that you’re visiting smack dab in the middle of a religious festival or cultural event and all accommodations are booked or prohibitively expensive, forcing you to spend the night in a sketchy train station or downtown alley.

If you are not ready to commit to more planning than you’re accustomed to, then just ensure that you do a bit of research or get local advice to avoid any unexpected glitches. To start, you should look at accommodation availability and train service during the specific period you are planning on traveling. This should give you an indication of what to expect and will tip you off if there’s some event going on at that time. You can also book hostels and some hotels ahead of time and bail if your plans take you elsewhere. You may lose your deposit (~10%), but you will wish you had a backup plan when you’re shivering on a park bench for the night.

Put yourself in group settings when you travel solo

I stayed in a small family run B&B in Rome. While it was a superb base from which to explore the city on my own, I didn’t think I could go five days with my only conversations occurring when I ordered food and gave museum attendants my entrance tickets.

I usually advocate for going on a tour when arriving in a new place, especially in a city like Rome with a large number of historical sites. I found a good city walking tour online which seemed popular with mid 20’s-ish travelers and which emphasized the cultural and historical significance of Rome’s ruins. The group was large, around 30 of us, many of which were also traveling alone, making it very easy to connect with other like minded travelers. It proved to be such a good experience that I signed up for an evening tour of Rome’s fountains as well.

In Florence, I opted to change gears and stay at Academy Hostel which catered to a more ‘mature’ traveler (ie. no bunk beds). I shared a room with three other single travelers, and met a bunch more. It was a breeze meeting people at this smaller hostel and I quickly found myself with some friends to explore the city with by day and drink beer with on the steps of the Duomo by night.

Ensuring that you have opportunities to be social and make connections with other travelers will make your trip more enjoyable and memorable. I also found that traveling alone made me much more approachable than I’ve ever found traveling with my boyfriend or with friends.

Be safe but not restrictively cautious.

One of my strongest hesitations to traveling alone, especially being female, was that it might be dangerous. I had some common travel preconceptions of Rome including rampant pickpocketers, aggressive Roman men, and pushy street vendors; all of which made me slightly wary of wondering out on my own.

When I arrived, I was debriefed by the owner of my B&B on the neighbourhoods of Rome and must see sites. I made sure to inquire about which areas were less safe for me to be alone in (Tremini at night) and what I could expect being on my own. There are dangerous areas in every city (including in my hometown of Toronto) and simple common sense will go along way.

Overall, I had absolutely no problem being alone in the city. As I wasn’t blatantly a tourist (ie. speaking English with my travel companion), I blended right in and was mistaken as a local by both tourists and Romans alike.

When traveling alone, you are the only one looking out for your safety. You are responsible for ensuring that you don’t put yourself in a dangerous situation. That being said, don’t close yourself off to valuable experiences just because you are alone. Thinking of gallivanting around the old city at night? Ask a local whether they would feel comfortable doing the same. Want to join some of you new hostel friends on the pub crawl? Just make sure you can make it back at the end of the night.

Do what you want to do.

This is the beauty of traveling alone. Do not feel pressured to follow the typical tourist trail. I’ve had numerous experiences traveling with others, some of which I genuinely enjoyed, while others, not so much. I am pretty easy going when traveling and tend to go along with what everyone else wants to do, which has not always worked out so well for me, especially when their interests were not aligned with my own.

I truly understood the benefit of traveling alone when I was in Florence. My first spot when arriving in the city was the Uffizi Gallery. Coming from the beautifully refurbished galleries and museums of Rome, I was in art overload and was beginning to exhibit the initial symptoms of Stendahl syndrome. While every tour guide directed me to the Academia to see David, I felt apprehensive. Instead, after being tipped off by another solo traveler, I opted to check out the obscurely fascinating La Specola, aka Museum of Zoology, which has a wide array of taxidermy animals and anatomical human waxes.

This is your trip and you can do whatever you want with it. If you’re a hardcore foodie in Madrid, then skip the museums and forge your path through the city’s best bites; If you are a literature buff in Dublin, tour the famous writers’ local haunts and inspirations. Being on your own let’s you fully indulge in your interests, which will enhance your experience a thousand-fold.

Increase your confidence in being alone.

I am not one to willingly engage in many activities alone in my own city, such as dining at a restaurant or seeing a movie by myself. The thought of doing so makes me even feel a bit panicky, which is why I couldn’t fathom doing these things in Italy. Whatever preexisting apprehensions I had about eating alone, however, dissipated pretty quickly as I walked famished from a busy day through the old city in Rome.

On the last stop of my trip in Cinque Terre, I arrived in the beautiful village of Vernazza. After walking the more intensive red trail from Corniglia, I found a spot at one of the many packed restaurants at the water, and appeared to be the only person alone in this unbelievably romantic town. But by this point in my trip, I could not have cared less. I enjoyed my leisurely lunch, vastly entertained by the exceptional people-watching opportunity.

Another unexpected benefit of my trip was that being on my own forced me to pay more attention to where I was going. Clearly as I described above, I am a lost cause when it comes to directions, or so I thought. Aside from that one incident in Rome on my first night, I successfully managed to navigate through the rest of my travels without a hitch, something that I still remind my friends of today. Whether they believe me or not is a different story.

For more travel tips or to learn more about how to travel solo, check out Departful’s Travel Tips section.

Travel Solo photo courtesy of Stocksnap.io; Ezra Jeffery