What does it take to get out and travel by yourself as a woman over 50? For some women, it’s easy. For other women, even the thought of taking a trip alone can feel pretty overwhelming. It takes courage. Can you relate?

One approach for women over 50 who are afraid to travel is to start by looking backwards to see how you handled a similar situation in the past. If you conquered that experience, you know you have it inside of you to do it again.  

And starting with a smaller trip first also helps. If you find a destination of interest not far from home, you can control your anxiety by starting and stopping the experience when you feel you’re ready.  

Similar to learning any other new skill, preparation can be an important factor in helping you feel more confident. For a road trip, make sure you check your tires and fill the tank with gas the night before. Check the weather and pack accordingly. Bring your phone and make sure someone knows your itinerary.

A Twenty-Something Solo Roadtrip

I took my first solo trip in my mid-twenties. One summer, a friend who had a condo in Ocean City, Maryland announced she was selling at the end of the season. She wanted to let a few friends enjoy the place before she put it on the market.

When she offered me a weekend, I couldn’t resist. I packed the night before and left right after work. Driving over the Chesapeake Bay Bridge, I remember having the radio turned up, the windows down and breathing in the salt air. I felt happy and free. I got to her condo late, watched the news and went to bed. The reality of being somewhere new by myself didn’t hit until the next morning.

Not having brought groceries, I had to go out for breakfast. As I stood in line with a talkative crowd of beach visitors in pairs and groups, I felt embarrassed when the waitress asked how many were in my party. “Just me,” I answered in a quiet voice. She smiled and kindly sat me at a little cafe table by a window. I quickly reached into my bag and pulled out a book to read so I wouldn’t have to make eye contact with others. The whole experience seemed strange.

The rest of the weekend, I started to relax. I enjoyed sunbathing on the beach until I got bored, strolling on the boardwalk at my own pace, and shopping in the stores I wanted to visit. I realized I was in charge with no one else to please but myself.

Although I got takeout for a few meals, I did go out for dinner to a nice restaurant the last night. By this time, I was feeling pretty empowered. As I drank a glass of wine before dinner, I decided to pretend I was there as a journalist, just observing everyone else for a story I needed to write later. Making eye contact didn’t embarrass me anymore. And I had a nice dinner.

A Woman Over 50 Solo Adventure

Fast forward to the fall of 2017. My life had changed a lot at this point because my kids were in college, I was separated, and I was recovering from a huge health challenge. I was living on my own and trying to figure out who I was now, and what I wanted the rest of my life to look like. 

The first outing I took by myself was to a local fair in a nearby town. I had always wanted to visit the annual Waterford Fair held in early October. I had read about it in the papers and heard the promotions on the radio for many years but had always been too busy with family events to go. Waterford is a historic town in Loudoun County that was founded in the early 1700s. It’s about half an hour drive from Washington, DC.

The fair is well known for having a wide range of crafts handmade in the traditional method by experienced artisans. Visitors can tour historic homes, stroll through the national landmark village, appreciate lively music played by volunteers in period costumes, and enjoy delicious food and drink.

I spent about six hours walking around, taking photos, eating lunch on a hay bale with the crowds, and just enjoying the fun of a classic fall experience. When I was tired, I left with hand-crafted souvenirs, a full belly and the confidence that I could still enjoy taking a trip by myself.

Still Learning – Almost Overcome By Fear

A year later, I decided to drive to upstate New York to go to a four-day travel blogging conference. It was a sunny blue sky day and I left Virginia feeling confident with a full tank of gas. I was fine driving through both Virginia and Maryland, but when I crossed into Pennsylvania, I had a moment of panic.

Somewhere deep inside, I started to doubt myself. “Who do you think you are taking this trip by yourself? Turn around right now. You can’t do this.” I’m not sure where those thoughts came from out of the blue, and I almost pulled over to the side of the road. Almost.

Then I took a deep breath and counted to 10 while I kept driving. After five decades of life, I have survived a lot of hard experiences. For some reason, I thought of the quote by President Franklin D. Roosevelt, “… the only thing we have to fear… is fear itself.” Yes, that definitely applied here.  After another deep breath, I said out loud, “Yes, I CAN do this trip!” And other than one stop for gas, I drove all the way to Corning, New York.

Meeting new people is always hard and I was both new to the conference and to the industry so I did not know anyone. Luckily, like many conferences, the staff scheduled events pre- and post-conference at scenic locations like wineries where attendees could meet people in smaller group settings. I met a few people at these events and at the lunches so I started to relax. I was glad for the name badges which really help when you are a first time attendee and you’ve traveled to the conference by yourself. 

One lesson I learned as a solo traveler on this trip is that picking an AirBnB on the outskirts of town might save money, but had its own cost since I lost out on some of the networking with others. I could tell a lot of bonding happened in the hotel lounges and over breakfast in the hotel restaurant. As a solo traveler, I would’ve felt more comfortable walking over to the hotel at night with other attendees instead of driving by myself to a suburban neightborhood 15 minutes away by highway. 

Adding Destinations Extends the Fun of a Trip

Since that first trip to Upstate New York, I’ve taken several trips by myself. I drove up north again this summer for a week long trip to Rhode Island and Massachusetts. I stayed part of the time with friends and part of the time by myself at hotels and AirBnBs. I flew to Montana for another blogger conference and met a great group of women who are now friends. I traveled over the weekend post-conference with one of them and saw Yellowstone National Park. I even added an extra day to my return flight from Montana to spend 24 hours in Seattle. I always wanted to go up the Space Needle because it was on my bucket list. I was finally able to check that one off because Seattle is a hub city for Air Alaska.

The Rewards of Traveling Solo as a Woman Over 50

Some of the lessons I’ve learned from solo travel as a woman over 50 are organizational. After struggling to close my suitcase because I overpacked, I’ve learned to take out 1/4 of what I pack at the end. I watched lots of YouTube videos so now I’m an expert at Marie Kondo folding. I can fit everything into a carry-on and a personal item even for a 10-day trip. Lugging heavy suitcases wears me out more than it did when I was younger. I’ve also learned to pack multiple chargers for my electronics because I carry a phone, iPad and a DSLR camera on most trips.

Other lessons I’ve learned are about trust. I’ve learned to trust my intuition more by taking the time to look at my surroundings and tune in to how I feel around people. If something or someone doesn’t feel safe, I turn the other way. And sometimes, trusting yourself and going in a new place can pay off. I’ve met some very nice people who were extra welcoming because I was traveling alone.

I’m very comfortable taking solo journeys now. But it took practice to develop the courage to travel by myself. Another silver lining is that I believe developing the courage to travel solo as a woman over 50 has made me more comfortable making other decisions in my life as well.

How do you feel about solo travel as a woman over 50? Is it hard for you? What lessons have your learned along the way?

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