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Traveling Alone at Midlife

What you learn about yourself while on a solo trip

Several months ago I had to travel to Lucca, Italy for work. Seeing that my airfare was taken care of, I was getting paid for what I was doing and I didn’t have to be anywhere “in person” for the following week, I decided to spend several days after the conference in nearby Florence. Yes, I decided to take a vacation in a foreign country by myself.
My planning was a little unfocused — I was really busy in the weeks before I left. But I downloaded guidebooks and apps onto my iPhone and iPad, including several that would translate phrases into Italian, a language I don’t speak. I picked the brains of people who had lived in Florence (and packed rainboots, which I ultimately never wore). I crowdsourced friends on social media about what to do about international phone calls and data. Usually an overpacker, I opted to wash undies in the sink and pack lightly (and still ended up with two dresses and one shirt I didn't wear).
All in all, the trip was a major success, and I proved that at 62, I’m still capable of solo traveling.
(MORE: Why Solo Travel Is the Way to Go)
In the months since, boomer friends have ruminated with me about whether they’d be up for an adventure with themselves as their main companion. I think the best answer is: “It depends.”

Spending so much time with myself, I learned or became re-acquainted with some of my good and not-so-great qualities. Certain traits made unaccompanied travel a breeze. Others provided moments of anxiety and discomfort I would never want to repeat. Here’s what I found out about being a tourist on my own — the good, bad and ugly:

I can plan a mean itinerary. Having control means I get to see what I want to see. I knew I had five full days in Florence, so I sensibly purchased a three-day museum pass that gave me line-free entrance powers to over 60 museums. I also wandered guilt-free into museums I knew were pretty dumb (like the house where Dante was born, which had “reconstructions,” but nothing authentic) and climbed every tower to take in the vistas of a “living museum” (i.e. the city of Florence itself), something tours often discourage because steps tend to be uneven, worn, steep and lack bannisters.

I also found online (and through recommendations) inexpensive guided walking tours. I booked one for my first morning in the city so I’d get the lay of the land. I left enough time in my itinerary for a day-trip to Sienna (which I did with a private tour service, my companions being a lovely elderly couple from Virginia who were visiting Italy “for the last time”).
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I was able to keep basic expenses on the cheap side. Sure, if there were two of us, the extra money for a larger room would have made sense. Since it was just me, however, I stayed in a tiny, inexpensive room in a small “boutique” hotel that was right near everything I planned to see. I was out most of the day, so having a view of a back alley didn’t bother me.

Also, “just me” meant that if I wanted a glass of wine at dinner, I didn’t have to pay for an entire bottle, as two people dining together often do, even if it remains unfinished.
I can be friendly with strangers. Chatting with people I don’t know in my local supermarket checkout line is one thing. Sitting down at a breakfast table with men and women I’ve never seen before takes a little more extroversion than comes naturally to me. Luckily, all the people at my hotel were nice and interesting; at the end of my trip, I exchanged email addresses with few.

Unless you’re perfectly content to spend several days uttering only “excuse me” and “the check please,” the readily-friendly will do better at solo travel than those generally more reserved.
(MORE: The Case for Eating with Strangers When Traveling)
I’m flexible. A steady drizzle that changed back and forth into a downpour pretty much put a damper on my excursion to Sienna. I would have loved to have spent more time walking around the small, walled city, but slick cobblestones are treacherous — and my older-than-I-am companions definitely needed an alternative. The driver suggested a visit to a vineyard (we were in Chianti country), so I switched my tourist setting from “historical sites” to “wine tasting.” Really, I would never have planned this myself, but the wines were great and the olive oil was even better.
I hate eating alone. I have no problem going to movies alone, though when I do, I miss exchanging arch looks with my companion during the best and/or worst scenes. I have huge issues eating without others at the table, though. It’s not that I mind having fewer dishes to taste. I just feel so lonely.

One night, I made plans with other guests at my hotel; another night, I met up with a friend of a friend. Both meals were fun and I should have made more of an effort to fill my dining hours with company. If you’re anything like me, I suggest you troll your friends’ address books seeking people they know in cities you’re visiting. (Lunch for me, by the way, wasn’t an issue because I generally had something to eat on the run.)
I get lonely. I was so busy during the day that I barely thought about missing my friends and family. Nevertheless, I was continually aware that I had no one special with me to share the high points (Michelangelo’s David, for one) or the little things (a shop window filled with hundreds of hanging cuts of cured meat). SIM cards and phone cameras meant I could send off pictures of what I was seeing, but the response, because of the time zone difference, wasn’t always instantaneous.
I am completely dependent on technology. I used to be great with maps, but now I need Google to ensure I’m walking in the right direction. I also convinced myself that email was essential because, technically, I was still working (and I did put in a few hours at the computer every evening).

Luckily, most hotels in tourist areas offer Wi-Fi, usually for free, and much of the world has better phone service than we do in the U.S. Next time I’m traveling by myself, though, I’ll probably pack hard-copy maps and a small physical dictionary/phrase book for those off-the-grid moments.


Sink wash at your peril. Keep in mind that underwear (or anything else) hand-washed at night might not be dry in the morning. I also decided to wash a cotton shirt after ascertaining that the hotel had an iron and ironing board I could borrow. Now, ironing is a skill at which I excel (if I must say so myself). However, the shirt would not de-wrinkle to my satisfaction. Also, half of the button-cuff-link must have disappeared down the drain because it was not to be found when I put the shirt on a hanger to dry.

Luckily, it was only my own clothes I was taking responsibility for. So this mini-adventure could actually be reworked into “The GOOD” category!
My solo-travel habits made me seem very “American.” After a full day of walking and sightseeing, by 6:30 p.m. all I wanted was to eat a little something, do a bit of email and flop into bed. In Italy, however, no one eats dinner that early; indeed, the restaurants aren’t even open. If I had been with my husband or a friend, most likely we would have gone back to our room, taken a short nap, had a drink and been happy to eat at 8:30 or 9, like everyone else. But, again, I called up all my adaptability and waited for dinner.
My cellular data strategy went awry. After much pre-trip back and forth, I decided to get a SIM card for my iPhone 5S from an Italian store when I arrived. I had not, however, investigated which company is considered the best. My phone did not work in Lucca at all, and I could not make phone calls in Florence, though the GPS for my Google Maps worked.

I had also forgotten my SIM card tool, and Italian paper clips aren’t the right size to be a substitute. Without the USA Verizon SIM card (which basically does nothing, but the Italian SIM card wouldn’t let my CDMA work), I couldn’t even call home when I arrived back in the U.S.       
When all is said and done, I’m sure I prefer traveling with someone than by myself. My solo trip to Italy, though, strengthened every boomer cell in my body.

I may have been lonely at times, but I was resourceful and strong. At some point, the exigencies of age may make guided tours a more sensible choice than solo travel. For now, though, this 60+ gal is ready for anything. Any work trip that is going to send me to an interesting place will, if I can make it so, involve a bit of vacation, too, even if it’s a vacation I take alone.

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