Solo Travel Over 50: Memorable Moments on the Road

There’s something magical about traveling alone. When you’re on your own, every experience feels more vivid, every challenge turns into an adventure, and every interaction with a stranger becomes a meaningful connection. As a woman traveling solo in my fifties, I’ve collected a treasure trove of moments that have shaped the way I see the world—and myself. Here are a few of my memorable solo travel experiences.

Navigating Spanish Highways Without GPS

Before moving to Spain, I took a “scouting” trip, planning to fly into Barcelona, rent a car, and drive down the coast, stopping in towns along the way in my search for my next home.  Since a GPS device is not always available in rental cars, I’d planned to use Google Maps on my phone.  But after landing at the airport and picking up the rental car, my phone inexplicably would not connect to any cell towers, so I had no service.  Knowing I needed to drive south on federal highway AP7, I followed the signs out of the airport, fingers crossed.  

Sure enough, I soon found myself southbound on AP7 toward my first town of Cambrils.  Once on the open highway, I restarted my phone, and it connected!  (Lesson learned: take time to connect the GPS before leaving the parking space!)  But as I made my way south to Cambrils, I paid attention to the highway signs.  I realized that even without Google Maps, I would have been able to find my way into town.  I’m a GenX kid, after all!  

Navigating (pun intended) my way through that little blip gave me a huge confidence boost.  By the end of the trip, I found myself ignoring Google Maps and veering off the main highways to explore little beachfront towns.  Tooling around in my little red Fiat 500, I felt able to handle anything that came my way.

The Art of Gift-Giving in Portugal

Shopping on R. Ferreria Borges in Coimbra

While visiting Portugal, I took a break from sightseeing in Coimbra to do some shopping along Ferreria Borges.  I wanted to bring back a scarf for a friend.  I knew very little Portuguese beyond “bom dia” (good day) and “obrigado” (thank you), so I took the time to look up “scarf” (cachecol) and “blue” (azul) on Google Translate.  Thus armed, I set out on my quest.

Because it was April, most clothing stores had spring clothing in stock – “No cachecois,” I heard over and over from shopkeepers who spoke no English.  I was about to give up.  But I tried one more store that had socks on display.  Inside, a very kind shopkeeper took the time to climb a ladder and fetch a box of scarves for me.  He spoke slowly and patiently, using lots of gestures, and brought out a mirror for me to try them on.  I still remember the name of the shop, Loja das Meias (Sock Shop), because he pointed to the word “Meias” and then raised his pants leg to show me his socks, with a big smile on his face.  Of course I purchased a cachecol azul from him, and I’ll always remember his kindness.

Learning the Local Language—One Hotel Stay at a Time

One place where you are more likely to find English speakers is in hotels, since they obviously serve tourists.  But I never assume and always start out with the few words I know in the local language.  I find that concierges, in addition to being a wealth of local information, are also patient with my attempts to speak their language, and often happy to teach me.

In the town of Sitges, Spain, the concierge noticed that while she spoke to me in English, I continued to try to answer in Spanish.  I had asked for restaurant recommendations, so she pulled out a map and asked “In English or español?”  When I asked for Spanish (“Háblame en español, por favor. Necessito practicar.”), she spoke slowly and clearly, all the while pointing out places on the map and drawing how to get there.  During that interaction, I learned “estamos aqui” (we are here), “izquierda” (left) and “derecha” (right).

More recently in Venice, my attempts to remember Italian learned years ago kept getting thwarted by the Spanish I’ve been speaking recently.  The smiling concierge, who spoke both languages plus English, laughed with me.  As she finished checking me in, she joked, “From now on, we speak only Italian!” Over my three-day stay, I looked forward to each encounter with her, often looking up phrases in advance so I could report to her about my day.  I don’t think she actually expected me to stick to Italian, and she was effusive in her praise for my admittedly terrible Italian accent!

A Hiker’s Reward in Hawaii

In 2021, like many people, I was feeling frustrated by the inability to travel abroad.  I decided to take a trip as far away as I could get on a domestic flight: to Hawaii!  Although I’d planned the trip to be a relaxing beach getaway, I couldn’t resist the lure of Diamond Head in the distance.

I took a bus to the Diamond Head Crater Trailhead and began my hike up the mountain.  Having spent much of COVID at home, I quickly found that I was out of shape and out of breath!  But with plenty of other hikers on the trail, I took my time and made my way to the top to take in the spectacular view! 

From there, I could see a secluded cove that looked perfect for a swim to cool off.  I made my way back down the mountain, bypassed the bus stop, and wandered through a small neighborhood to reach the entrance to the cove, which I had virtually to myself!  Thus refreshed, I hiked to the next bus stop to catch a bus to my hotel.  I slept well that night!  That cove is still one of my favorite spots in the world.

My own private cove in Hawaii

A Venetian Evening to Remember

One of the best things about my recent trip to Venice was the quiet of the city in January.  Again without cell service, I was forced to find my way around.  I had a hotel map tucked in my bag, but I rarely used it, preferring to wander on my own, get lost a few times, then backtrack and learn my way around.

Venice is a city that is jammed with tourists in high season, so January was a pleasure.  Every turn led to a quiet plaza with only the sound of water lapping against the sides of the canals.

On my last evening, I sat outside my hotel at the cafe along the lagoon, looking south toward the lights on the island of Giudecca.  I ordered dessert and a drink, and as I dined I watched the boats glide along the lagoon.  While I’d be sad to leave the next day, taking my time to wander off the beaten path had left me with some lovely memories.

Venice at night

The Beauty of Solo Travel

Each of these experiences reinforced one of the biggest lessons I’ve learned while traveling solo: being open to the unknown makes every trip unforgettable. Whether it’s overcoming a logistical challenge, embracing new cultures, or simply savoring a quiet moment in a breathtaking location, solo travel has a way of reminding me just how capable and resilient I am.

If you’ve ever thought about taking a solo trip but hesitated, let me assure you—it’s worth it. The world is full of surprises, kindness, and moments of pure joy, just waiting for you to discover them.

What are some of your most memorable solo travel experiences? Share them in the comments—I’d love to hear your stories!