Unpacking Solo Travel with Jana Roe Osofsky

Last month I introduced a new interview series called Unpacking Solo Travel where I chat with women about their solo travel experiences. This month’s interview is with Jana Roe Osofsky. I did not know Jana before our conversation, but I was quickly blown away by her incredible story.

Today Jana is a joyful newlywed living in Florida with her husband, Marshall, but her adventures in solo travel were originally inspired by the tragic loss of her first husband, Eric. While Jana originally set out on her adventures as a way to pay homage to dream trips they planned together, she found solo travel to be a place where she could mourn her loss and rediscover herself.

Can you share with us about your travel background and what led you to solo travel?

We talked about her first solo trip, the benefits of traveling alone, the anxiety that sometimes surrounds the idea of returning home, and what advice she would give another woman considering traveling alone.

I was married for about nine years to my college sweetheart, Eric. We were together for 16 years. In college, he was diagnosed with a very rare kind of slow growing cancerous brain tumor. We dealt with it for our entire marriage. There were times when he was in treatment, and there were times when he was not in treatment; but unfortunately he lost his battle in 2010.

It was a very odd situation because I knew from the time that we got married there was a good chance I wouldn’t have him forever.  So I had a chance to really process that over the years. One of the things we really enjoyed doing together was traveling. We did as much traveling together as we could, and we always really enjoyed it. In the last couple of years of his life, there were trips we had planned that we had to cancel. So I wanted to go and do those things. I ended up doing some of those things, but I also did a lot of other things that we had never even imagined we would do together. I did a lot of traveling in that first couple of years after he passed.

Unpacking Women's Solo Travel with Jana Rae Osofsky - Her Bags Were Packed

I can only imagine what an incredibly emotional time that must have been. What can you tell us about that first solo trip?

I decided, at the last minute, to just jump on a plane and go to Brussels. There was a group tour, the following week, that started in Brussels and ended in Amsterdam, but I decided to go early. So I was in Brussels, of all places, by myself for a week. By day I would go out and explore and do so many things.  And I was happy and my heart was so free. But then at night I would go back to the hotel room, and I would just cry and cry. Even at the time as it was happening, I knew that was exactly what I needed. Being by yourself gives you the room you need. It’s pure catharsis without having to worry about what other people are thinking about how you’re acting or what you’re doing or how you’re prioritizing things.

By the time that week was over, I was ready to join the tour group. I felt like I had kind of transformed in a lot of ways. I was a clean slate, and I was able to enjoy the tour and the people and experiences in a way that would have been really hard if I had not taken that week alone before it started, if I had played it safe.

My experience truly is what Her Bags Were Packed is talking about, the embodiment of utilizing solo travel, not only as an opportunity for self growth, but really as an opportunity to release emotional baggage.

How did you decide where to go? Were you basing your destinations on specific trips you had planned with Eric or was it more random than that?

We definitely wanted to go to the low country part of Europe, like Holland and Belgium (places I have since been) but we also wanted to go to northern Europe and Scandinavia, and I still have not made it there. That was one of the trips we had to cancel, and it’s still on my list of places I’d like to go. When I had the opportunity to just take off for Brussels and Amsterdam, I was sort of fulfilling one of the things we had wanted to do together.  Subsequently, in that same year, I spent a long time in France, and I don’t know that that was really something we had talked about together. I also went to Russia with my grandparents, and that was a place that we had wanted to go and see together.

Unpacking Women's Solo Travel with Jana Rae Osofsky - Her Bags Were Packed

People often ask about ways solo travelers can stay safe. What are some of your strategies?

I play it pretty conservative. When I’m traveling, I like to get up early in the morning. I tend to wander in the morning and then have something to do in the afternoon. Because of that, by the time it gets to the point where it’s dark out, I’m exhausted and I end up going back to the hotel. I keep my eye out for restaurants close to the hotel that I might want to go to, and I do try to stay in places that are off the beaten path, so that when I end up at a restaurant three blocks from the hotel, it’s not some lame touristy restaurant.

And even though I love to go out when I’m at home with my husband, for some reason when I’m traveling I don’t really have any interest in nightlife. Maybe it’s because I developed my habits as a solo female traveler, but I just feel like nightclubs are nightclubs wherever you go. I don’t really find that to be a big part of the culture. And to me, that’s where I would think women run into problems. So I just don’t do it.

Women often ask about how and if they will meet people while traveling. What has been your experience with this?

It’s funny, because you start off alone and you pick up people along the way. Some of the people are people you meet, and some of them are people you reconnect with. On the Brussels tour, there were two other women who were also solo, and we’ve ended up going on two other trips together in the last seven years. But at the end, I was planning to be by myself for about 10 days in Holland and Amsterdam. I made plans to meet up with a cousin I hadn’t seen in a long time who lives there, and I ended up staying at their home for about a week. It was such an amazing experience because it ended up totally different than what I had planned. That’s the kind of opportunity you can have when you’re by yourself.  

Unpacking Women's Solo Travel with Jana Rae Osofsky - Her Bags Were Packed

Something that often comes up for me at the end of a long trip is sort of an an anxiousness around returning home. I feel like I have learned so much about myself and worry about losing that when real life hits. Have you had any experiences like that?

I always have a sense of nervousness about coming home from longer trips. It’s not that I don’t want to come home, but it’s that slightly depressed feeling I would get as a kid coming home from summer camp. I was leaving behind all those friendships, relationships and experiences, and I guess when you are traveling by yourself the equivalent of those summer camp experiences and friendships are the ones you are redeveloping with yourself. So coming home sort of feels like the end of an era.

What advice would you give other women who are considering solo travel?

Anyone who is considering it should absolutely just plan a trip and do it. The worst thing that can happen is you don’t have a good time and you don’t do it again, but that’s so unlikely because it’s such a gift to yourself. To give yourself that time to go somewhere you want to go and not have to negotiate your choices everyday:  where you are going, how long you will stay, what you are going to eat. I think if someone has any inclination to do it, they should absolutely try it.


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