Falling in Love with Solo Travel After Retirement: Women Who Travel Podcast

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Charlotte Simpson had been traveling for decades before she took her first solo trip. She had visited all 50 states with her late husband throughout their 31-year marriage, traveled internationally with her daughter, and had adventures with girlfriends. But when no one wanted to go on a trip to Italy with her a few years after her husband died, she set out on her own—kicking off a new love for solo travel and the freedom that comes with it. “It was so liberating,” she says. This week, Charlotte, known online as @TravelingBlackWidow, joins us our I Deserve This series, talking about how she prioritizes traveling for herself, what she’s learned about being more adventurous later in life, and how social media has influenced her travels.

Thanks to Charlotte for joining us and thanks, as always, to Brett Fuchs for engineering and mixing this episode. As a reminder, you can listen to new episodes of Women Who Travel on Apple Podcasts, Spotify, or wherever you listen to podcasts, every Wednesday.

Read a full transcription below. 

Meredith Carey: Hi, everyone, and welcome to “Women Who Travel,” a podcast from Condé Nast Traveler. I’m Meredith Carey, and with me, as always, is my co-host, Lale Arikoglu.

Lale Arikoglu: Hello.

MC: This week we’re continuing our I Deserve This series, which offers a space for us to explore all the conflicting emotions we feel when it comes to spending our time and money on ourselves, especially when it comes to travel. Joining us today is someone who seems to have mastered prioritizing her dreams: Charlotte Simpson. Known on Instagram as @TravelingBlackWidow. She’s visited all seven continents and all 50 states on a combo of solo trips, vacations with her daughter, and adventures with friends. Thanks for joining us, Charlotte.

Charlotte Simpson: Thank you so much for inviting me. I am so tickled to be here.

MC: We’re so excited to have you.

LA: And I am so envious that you have visited all seven continents and all 50 states. That’s absolutely extraordinary.

CS: You live long enough, and it happens.

LA: As Meredith mentioned, a lot of it was solo trips, but there’s been a combination of vacations with other family members and friends. Before you started doing all this solo travel, what was your relationship to traveling and being on the road like?

CS: I’ve always enjoyed traveling. And when I met my husband, when we were dating, he said once that he wanted to get to all 50 states, and that was just right up my alley because I just liked to go any and everywhere and he did too. So we made that our mission, and we did get to the 50 states, and out of the country. For our honeymoon, we toured Mexico.

But we always loved travel, so it’s always just been a big, big part of my life. And when he died, after I went through the throes of grieving and all, I still had that burning wanderlust and still just knew that I wanted to continue traveling and seeing the world—probably even more so, because I was by myself and didn’t have him. And it just gives you so much to look forward to. So I think I really ramped it up after he was gone.

LA: When you say you ramped it up, was it a conscious decision to ramp it up or was it that you dipped your toes in after you lost him and thought, okay, I’m enjoying getting back out there by myself. Maybe I’ll do it again. Was it a slow process or a really active decision?

CS: Well, actually it was a slow process. I was still working and I was an educator, but I really didn’t like to travel in the summer, but I did. I mean, it was really the only time that we could, then or Christmas break. So I would go someplace in the summer, usually like one trip and then maybe a trip at Christmas. But when I retired and had so much more time, just the passion got even greater, because as you probably know too, on a trip, you meet someone and they’re like, “Oh, you think this is great. Well, you should see so-and-so.” And you leave a trip with this list of other places that’s better than where you just went that you thought was so awesome. So that began to happen. And so I did, as I say, ramp it up because I was able, with not having to work, to travel with the good seasons for a particular place. So I started in the winter going to warm places and in the fall going to places that were really beautiful in autumn. I ended up then maybe doing more so about four or five trips a year.

MC: What were those first solo trips like for you? And what was it about those trips that made you realize that you really wanted to be exploring, regardless of who was coming with you?

CS: The first solo trip was a 15-day trip to Italy and I had never really planned to travel solo. I didn’t really want to travel solo. I don’t think for most people, it’s not something that just comes naturally to do. When you think of going somewhere, you think, oh, I’ll call so-and-so or I’m going to let so-and-so know. You don’t really think, oh, I’m going to this place. But nobody wanted to go to Italy. And so I just really wanted to go so much that I thought, I’m just going to give it a try and just see.

Anyway, I went to Italy by myself and I had such a great time. It was so liberating in a way. I can’t even think back now to remember if I really was ever sad being alone or really missed anyone, because you’re in Italy, so you really aren’t spending a lot of time thinking about who could be there. I do remember just going out sometimes for walks, which is not something I necessarily would’ve done with a girlfriend and even just going in grocery stores. Because all that time that you would be with someone doing something, later in the evenings and all, I just would walk around by myself and I just found I just enjoyed it. I saw so much more. I was much friendlier. I met so many more people. And just all around, it was just a real positive experience. And I knew it wouldn’t be my last solo trip.

MC: I can only imagine, that while you get tips from people on the road of where you should go next, that now with your Instagram following, you get tips from strangers on the internet. How do you think social media has changed the way you move around the world?

CS: Well, it really does have a big influence, I’d say, because when you’re looking at people’s travels every day, certain places become so appealing. And even places that you hadn’t thought about. When I came on to Instagram, Dubai was the hotspot. Everybody was going to Dubai. They were all posting pictures out in the dunes, in the desert. And they were just having the best times at the fabulous hotels. And I had never thought of going to Dubai. I had no desire to go to Dubai. But when you have seen at least 10 or 20 pictures every day, week after a week of people having such a wonderful time, it’s like, “Looks like I’ve just got to get over there and see what it’s all about.”

And even though the things that I saw in pictures… Because it would be a lot of shopping and eating. And I thought, gosh, I really don’t want to fly that far to shop and eat. It seemed like the dunes would be the other thing. It’s like, “I don’t know,” but I just had to see it. There’s like a pressure, because even too, when you would say, “Oh, I’m going to Morocco,” people will be like, “Oh, but have you been to Dubai?” Like, “No, I wasn’t really thinking of Dubai.”

LA: You’re like, “I want to go to Morocco.”

CS: Yeah. “You’ve to go to Dubai.” So back, I’d say, in ’14, ’15, 2016, everybody was going to Dubai. And so I went to Dubai. And there were a few other places like that. I think Iceland was another one that was just really on everybody’s radar. And fortunately I really liked it. I’m glad I went, but it definitely does influence where we go. Because like right now, I would say Bali is really hot. As soon as people can start traveling again, Bali and Maldives. I went to Bali before it was a hot spot. So I almost feel now like, oh gosh, I missed some of these things I’m seeing on all the pictures. I need to go back.

MC: This means you’ve got to go back. Exactly.

LA: Love an excuse for a return trip.

CS: Right.

LA: Just staying on the subject of social media for a bit longer, having a large following like you do also means that you’re very visible online, and in your travels. Has that been challenging to navigate, as someone who has a lot of followers who are commenting and asking questions and traveling along with you?

CS: I guess it does give you this kind of a Rick Steves or somebody, or a Samantha Brown kind of feeling. Like, “All right, I need to really be knowledgeable about this place because people are going to be asking questions and I can’t just be over here taking a bunch of pretty pictures of things.” I’ve got to have a little something to say with it. I’ll be writing captions. I do think you do feel this responsibility knowing that you will be putting out these pictures. Lots of people will be looking at them and expecting to learn something. I’m an educator. I don’t want to just post a picture and I’m in a big flowy dress and I don’t have anything to say. I want it to be about something.

MC: You mentioned earlier that on that trip to Italy, it felt really liberating to be traveling on your own. And going back to solo travel, it really allows us to prioritize ourselves in a way that no other trip really can. You’re going on walks, you’re doing the things that just you want to do. What do you think that sense of freedom that comes from solo trips has taught you about yourself?

CS: Well, I think with every trip, initially, it really made me more and more confident just about things that I could do. Because on a trip, when you’re with a friend, even something like riding a camel. Before I went to Morocco, I was… Well, actually the first time I went to Morocco, I was with my daughter and it was just the Christmas after my husband had died and we went to Morocco. And, we stopped at the place with the camel rides and she rode the camel and I’m like, “Oh, I’m not riding a camel, I’m scared to get on a camel.” And all the pictures, I’m standing there next to the camel. And I even had a skirt on, because I knew I was not getting on a camel. Well, this last time I went in… What? ‘19. And, I was all over the place in the Sahara with that camel. And it was no big deal.

I mean, each time you’re somewhere, you try a little something, you’re by yourself. It’s like, “What the heck?” You see everybody else doing it and you don’t want to just stand there. And so, I think you just experiment a little bit more. And with everything you do, just like anything else in life, every time you achieve some little goal, then you’re just stronger and better capable of the next one. So now, I just don’t know what might come up that I wouldn’t at least try.

MC: Are there any places that you feel like are particularly open to solo travelers, or that are really easy for a solo traveler to get around and meet people? Are there any places that you’ve been that you just think, “Ah, this is what I would recommend?”

CS: I guess, since I haven’t had any kind of stressful or unpleasant experience anywhere, it’s just really all been good. I guess, maybe I would just say a place where you might feel a little more comfortable with the language or the culture. My favorite place in the world is India, and I’ve gone like three times and been alone the three times I’ve gone. But, I probably wouldn’t necessarily recommend it to someone for their first time, because it is just so different that it could be sort of just culturally shocking to you, unless you had really read up on it, and maybe seen some movies and stuff.

But even there, if you’re excited about going someplace, wherever it is, if you were excited and you’ve been longing to go to that place, I just really think you are going to view it in a positive manner and you’re going to enjoy it… And, if you know that it’s someplace that might be dangerous, well, you know that, and you’re ready for it and you’re still willing to go. So, you’re going to be prepared. You’re going to be cautious.

LA: It’s really about educating yourself about the destination and basing your decisions on that, right?

CS: Definitely, definitely.

LA: Staying on the subject of planning for a moment, just because you are such a super traveler and you do, do so much of it solo. I’m interested how you actually plan your itineraries. And once you’re on the ground, do you kind of wing it or are you signing up for group tours, or connecting with people that you may have mutual friends with once you’re in a destination? How are you shaping these trips?

CS: Well, most of the time I will buy a package trip. And that, I think, gives me a lot of peace of mind. And, I would really sort of recommend that to someone, especially going solo their first few times, because everything is planned out. I call it mindless travel. You arrive at Bangkok or Shanghai, wherever it is, and the guide is there. He’s finding everybody in the group you’re forming. And from that point on, you are with that group of people. And every morning, you’re meeting in the lobby of the hotel and checking out three days later, whatever it is. So, it’s a very, very simple way to travel. I especially enjoy it, because I don’t want to be lugging my bags around. I don’t want to have to deal with all the logistics at all. And so, you don’t.

So, I would highly recommend doing a trip with a company. But, places that I have gone by myself or places that are pretty easy to navigate, and you know in advance, say like Paris, you know all the things that you want to see, you’ve seen enough movies and documentaries, and other people’s pictures. So, you know before you go, you can sort of plan out the week or however long you’ll be there.

But on some of the others, I really like and have been able to relax and enjoy myself, and feel very safe and secure. Because I know that there’s someone, that tour guide, if I’m not down in the lobby the next morning, she or he is going to wonder, “Well, where’s Charlotte?” And, they’re going to find me. And if something happens, they will help with that. And as I get older, I doubt at this point that I’m really going to start going to places just totally planning it all by myself, when I could just do something with the group.

MC: I also feel like we’ve talked about on the podcast before, how, if you’re starting out in solo travel or aren’t wanting to handle the logistics, group travel also gives you a built-in group of people to make friends with without having to necessarily if you’re—not even shy, but just kind of getting your footing on making new friends in a travel setting—you automatically have people to go to breakfast with, and to eat dinner with, wander around a museum with. You’re not completely on your own, starting from zero making new friends.

CS: Right. Because even if everybody’s paired off, which normally they are, and sometimes it’ll all be couples, not even like two girlfriends, it’ll all be couples and they’re paired off, but still there’s somebody that is good at photography. You’ve got those people with the great big cameras that are there, so you’ve got that help with photos and yeah, like you said, somebody that you could sit with at breakfast, if you want to sit with someone. But yeah, I definitely would recommend it.

LA: And to go back to the sort of topic of prioritizing yourself, the flip side is also that you don’t have to be loyal to anyone in that group as a travel partner. You can splinter off on your own and do whatever you want if you get sick of them.

CS: Absolutely. It sounds like you’ve tried this. Now having traveled so much alone, it is sort of weird when there is another single woman in the group, although they’re always pretty independent. It’s pretty rare that someone’s going to be like, oh, let’s sit together at dinner, oh, you want to go for a walk this evening. It really sort of doesn’t happen. And sometimes, in the evening, I’m out walking around, I might see this other single person and they’re down the next block and bargaining over something. So I think that person that travels alone, they have learned to enjoy their own company.

LA: I feel like people tend to have a lot of, and I’ve actually in my notes written this like in asterisks to emphasize, a lot of people have a lot of opinions when a woman makes a big life change and starts to prioritize herself in new ways. How do you think those around you responded to your decision to start spending so much more time on the road?

CS: I think some of them were really sort of surprised because I’d been married for 31 years. And so friends and coworkers pretty much knew me as a married coworker and a lot of us are Facebook friends. And so at first, some people would be like, “Well, what are you up to? I don’t. I don’t…” They would almost be confused. And I think they assumed that I was traveling with someone and just if I would post a picture and just somehow that other person was maybe taking the picture. And I didn’t really get into it that much because I just didn’t get into it, explaining myself on Facebook—I just posted pictures. But I think they were just a little surprised.

I think because so many of my friends are still married and in a way they don’t see themselves having the need to travel alone or wanting, just like I never wanted to travel alone. It wasn’t even about not wanting to, it just didn’t occur to me as a wife to travel alone. And as a matter of fact, the first trip my daughter and I did together when we went to Morocco at Christmas and there were two ladies who were alone and I would ask them like, why—and I feel bad now for asking what the tone that I used—but I was like, why are you and it’s Christmas? Because I just couldn’t understand.

As a matter of fact, just the other day, a former coworker, well anyhow, the other day, she announces that she’s retiring from teaching at 55 and I’m like, what? I couldn’t believe it. And she’s always saying how inspiring my pictures are and she just had no idea I loved travel so much. And I do feel part of it is just actually even after this last year, that people sort of look at their lives a little differently and she’s single, she’s always been single. And I think she just feels like, hey, there’s a whole big world out there and I am just going to just even try solo travel. I really think she’s going to try solo.

MC: And kind of to that point, I think after a year at home, we’re all feeling a little rusty when it comes to solo travel because we’ve been not doing it for a year and a half. What are some of your tips for easing back into it or things that you’re considering when you start planning your upcoming trips or even advice for people who might want to try it for the first time after the pandemic?

CS: Well, that’s also a really good question because I always think of myself as having systems, that I have all these systems in place for when I travel. And I mean, there’s just all kinds of systems. And so it makes everything flow very, very smoothly. As an example, like once I’ve checked my bag at the airport, then I just sort of look and see, okay, I have three things. So that’s my number, three, my coat, my purse, my rolling tote. Anytime I walk out of a bathroom, if I get up at a restaurant, remember, three. You need to have these three things with you.

And recently, a few weeks ago, my daughter and I went to Washington, D.C. I’d always wanted to see cherry blossoms in spring. And so we went to Washington and when we got to the airport, I was like, oh my gosh, what are my systems? I know I have systems, but what are they? And what am I doing? What did I leave at home? What did I leave in the Uber? I mean, I just felt so, so out of it. But now having experienced that trip, I would say, well in advance, just start maybe even making a list or just jotting down little things. Just get organized as early as possible.

MC: Something that I’ve had to think of, kind of like you’re saying about getting organized, is I keep having to remind myself those systems and trying to remember them earlier so that by the time I get to the airport, I’m prepared and ready to travel again. And I think just like I never would run through a trip in my mind ahead of time or I’m, Lale knows this, I’m a very last minute person at the airport. I get there in the nick of time, and I think recently I’ve been thinking a lot more about giving myself more time because I’m not at the same speed I was when I could rock up 20 minutes before my flight left.

LA: Well, we’re holding so much more in our heads as well, traveling and getting on a plane means so much more than it did a year and a half ago. A shout out when you’re talking about sort of forgetting things and feeling kind of disoriented on taking that first trip, I think is like because I don’t know, I don’t want to speak for other people, but I feel really unmoored right now and sort of just sort of slightly adrift. And I think when I’m thinking about where I want to travel next and taking those trips, it sort of feels like an attempt to sort of snap myself out of that a bit. Is there anywhere you are itching to get to as we start traveling again, both domestic and international?

CS: Well, internationally, I have suppressed my desire for any particular place for so long and in order to maintain my joy for over a year now, I really just have not allowed myself to think about where I really want to go. So I just really haven’t. I had three trips that were canceled. So now with the vaccination and the vaccine passport, or whatever it is, I’m finally just starting to think about it, and I guess even now I really don’t want to get my hopes up. So I guess just in guarding my heart a little bit, I can’t say there’s someplace I’m just dying to go right now. There are places I still want to go. Definitely, there are lots of places. I would love to go to Namibia. I feel like who knows when that will happen. I just can’t even imagine when that’s going to happen. I’d love to go back to Kenya and Tanzania, but I don’t even give it a thought. I do hope maybe within the year to go to Eastern Europe. I haven’t been to Hungary, I haven’t been to Croatia and some of the places there. I would like to get to those. And the companies that I deal with, they’ve all been offering trips to them and I’ve just been just a little reluctant. And surely at some point I’ll feel better about it, but I guess we’ve just all gone through so much heartbreak in so many ways in the last year that I’ve just started guarding my heart a little bit now.

MC: Is there anywhere closer to home that you’re substituting in for those far-flung places? Anywhere closer that you’re thinking has now probably like bumped up a few spots on your list of wanting to go there?

CS: Well, I really want to go back to the Pacific Northwest. My husband and I loved Seattle and Portland. We flew into Portland and explored that area and then drove up to Seattle and stopped at national parks along the way, and went over to Canada, to British Columbia, to Victoria. And I would love to do that again. And my daughter would like to do that. So perhaps this summer, if things continue to improve, I think she and I will get out to the Pacific Northwest.

But I mainly want to just sort of drive still for a while and just explore our country. The United States is so fabulous. Each state is so uniquely fabulous in its own way, and I could be very happy going back to New England, or out west, the national parks there, Utah, those are just some of the most extraordinary sites really in the world. When we were out at Grand Canyon, I mean, there were people from all over the world there.

MC: So I know we’ve been talking a lot about solo travel, but we’ve mentioned your daughter a few times. Do you have any hot tips on planning and surviving a successful mother/daughter vacation?

LA: Love this.

CS: Oh wow. Okay. I would say to have a great trip with your daughter, think of your daughter as… And my daughter is a great, great friend. We get along very, very well, but to make sure that that happens on a trip, I try to think of her as a really finicky friend that I am trying to please and get along with. And not that I have to bend over to please her, but I just feel like if I look at it like say my finickiest friend, what would I do? And so once again, there’s like systems that she and I both sort of have in place for being respectful to each other and being able to enjoy each other’s company. And we always want to go to the same places, but just in the event that there isn’t, then there’s no discussion of it. Once you say, “Oh, I don’t want to go see the Eiffel Tower,” it’s like, “Okay, I’ll just go by myself then.” There’s not going to be arguing or trying to coax her into doing something that she doesn’t want to do. Because it’s her trip, too, she wants to have a good time.

So I just think being really, really courteous and thoughtful of your daughter because, I mean, you just want to get along. You want her to have a really great time. That’s always my thing. Sometimes if there is something where I want to get into like, “Oh, come on, let’s do whatever,” then I think, I want her to go with me next time, I don’t want her to say, “Oh, but then we always have to eat where you want to eat.” I want her to have a good time. I want her to feel that if she doesn’t want to do something, she doesn’t have to do it.

MC: And I think that what you mentioned about regardless of whether or not it’s your daughter, if the person that you’re traveling with doesn’t want to do a thing that you want to do, you just do things separately that afternoon and then you come together and you have things to share with each other. No harm, no foul, just everyone is having a good time.

CS: Right.

LA: Well, you sound like a fabulous travel partner, I have to say. I want to go on a trip with you.

MC: If people want to keep up with your travels, Charlotte, where can they find you on the internet?

CS: Well, I’m on Instagram and Facebook, and then my website, travelingblackwidow.com. So I hope they’ll stay in touch.

MC: Amazing. I’m @ohheytheremere.

LA: I’m @lalehannah.

MC: We will link Charlotte’s social media and her website in the show notes, as well as links to Women Who Travel’s Instagram and our newsletter. Thank you so much for joining us, Charlotte, and we’ll talk to everyone else next week.

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