I love it. I’ve been doing it for years on business trips to Europe. I remember the one time I just got to May Fair where I was staying in London. It was late, my colleagues were at home with their families… so I took myself out for dinner at this lovely Indian Restaurant.
When I started consulting, my schedule didn’t match those of others, so I took the solo vacation plunge. Easy for me to say for Italy, I have family and friends there. But the same thing happens with calendars – so I’ve done my fair share of solo exploration.
I’m a fairly independent person, I like the sense of control when I’m on my own. As an introverted extrovert, when I’m alone, I actually tend to do much better meeting other people. Have you noticed something along the same lines?
So here I’d like to put forward some thoughts about the advantages of traveling solo – and the drawbacks. See how they feel to you.
Going at your own pace, doing what interests you, eating where and when you like
There are definite perks to being solo that you can transfer easily to travel scenarios. How about a morning of shopping? Treat yourself to a special something. Maybe even splurge a little. You can stop and eat when you’re hungry, stay at Airbnbs and buy at fresh local markets.
In the summer, a nice stop at a café (“

Walking around alone helps you connect more closely with the city. You can take in the sights, sounds, scents, and rhythms all around you. Exchange a few words with people in the shops, or cafés – being alone, you’re more approachable. It gives you a chance to find out what people think.
Some cities offer bike tours – something to research and plan. Along the same lines, you can find plenty of entertainment. Things like open theater movie nights in summer, or concerts, shows, museum tours any season. Go where the path leads you.
I’m an early to bed and early to rise kind of traveler. But sometimes a night stroll in well-lit city centers is a wonderful experience.
No built-in dining companion, or someone to send ahead while you wait in line
And sometimes you can feel a bit lonely, especially when you’re trying to figure out bus or train schedules in another language. I get it. It’s also disappointing not to share a moment of discomfort when you get lost, or things don’t go as expected.
These are first world problems, aren’t they? But there are also some pragmatic disadvantages. It’s usually more expensive to book hotel rooms with single occupancy in Europe. Other things cost less when you split costs – groceries and taxis, for example.
It’s harder to have fun when you’re having a bad day. Traveling solo in general takes a bit of practice. If you’re not used to being alone, it may be tempting to let technology entertain you. Or is it distract you? You could be noticing something interesting instead.
Safety is a concern. Although many of the cities I visited in the last ten years have felt safe, there are worth thinking about. Staying in well-lit and busy streets at night, using a cross body purse, leaving the passport in a safe place, keeping pocket money separate from cards are just a few examples.
Why it’s an equally great experience as a sabbatical, and a shorter trip
For different reasons. It would give you enough time to become local with a longer time frame. But if there’s a place you always wanted to see and don’t have more than a week, you can cover a lot of ground in Italy in a week.
I slide a spiral notebook in my bag to jot down observations as I go. My creativity skyrockets.
Socializing on your own is as simple as smiling more often. Put down your phone and try a “ciao,” or a “buon giorno” and see what happens. If your trip solo was to celebrate a special occasion, it’s a chance to meet new interesting people. Wink, wink. Or maybe to take stock and reflect.
Trains are great for meeting new people. You almost always find a reason to talk about the view, or your destination. Go to the dining car to get a drink and stretch your legs. Simple orders like a drink is a good method for practicing your language skills – “una birra, per favore,” “acqua frizzante,” “un bicchiere di vino rosso.”
A good way to practice is to take yourself out to the theater in your home town or place of work. I took myself to see a Broadway matinee in between meetings on business travel. I saw people going in, stopped by the window, got a great ticket in front, and loved it.
Regardless of how you feel about solo travel, the sense of freedom and self-reliance you experience when you try it will invite you back for more.