Rewriting Traditions: Solo Women, Travel, and Healing Through the Holidays

The calendar flips to October and the store aisles explode with tinsel—meanwhile, your heart feels heavy at the thought of the holidays. If you’re a single woman or newly navigating an empty nest, those weeks between Thanksgiving and New Year’s can feel like a pressure cooker of memories, expectations, and silence. We decided to tell the truth about it—and share a better way to move through it.

We start by naming the hard stuff: sadness, loneliness, grief, and the ache of feeling like the odd one out at someone else’s table. From there, we get practical. You’ll learn how to map your emotional and physical needs, choose travel that supports them, and time your bookings to avoid sticker shock. We talk road trips that keep costs low and control high, why international travel can be a hidden bargain during U.S. Thanksgiving, and how a cruise or city break can flip the script on a day you’ve come to dread.

We also dig into rituals that turn grief into meaning. Think small, tangible acts—gifting keepsakes that carry a loved one’s story, volunteering in their honor, cooking one dish that keeps their light at the center of your table. We draw a bright line between being alone and feeling lonely, then offer concrete ways to connect: inviting yourself to a friend’s dinner, gathering other solo travelers, or joining meetups at your destination. And for Christmas, we walk through choosing family time that feels safe and nourishing—or building chosen family traditions that fit who you are now.

If you’ve been waiting for permission to design a holiday season that heals, this is your nudge. Press play, take what serves you, and start a tradition you’ll actually look forward to. If this conversation helps, subscribe, share it with a friend who needs it, and leave a review to help more women find their way to joyful, self-made holidays.

Chapters

• 0:00 Setting The Holiday Stage
• 2:45 Naming Hard Feelings
• 6:10 Decide What You Need
• 8:50 Smart Holiday Travel Timing
• 12:30 Choosing Thanksgiving Plans
• 15:40 Grief Into Meaningful Rituals

Transcript

SPEAKER_00: 0:00

Hello, sister travelers. Welcome to Solo Travel Adventures. I'm Cheryl Esh, your host. Well, I hear a lot that around this time we're in the beginning of October, that oh my gosh, the holidays are right around the corner. And so if you are in the US and celebrate, we do have a traditional holiday coming up here in November in Thanksgiving, always celebrated the last Thursday of November. And then right on its heels is all your, you know, your Christmas or your Hanukkah celebrations that follow the following month. So it gets a little crazy, and you know, often people will travel to be with loved ones during this time. So a lot of domestic travel happening during this season or between those holidays. So I want to speak to my single ladies out there right now because this can be a really um challenging time of year for you. It could also address anybody that's maybe a first-time empty nester. So you might be experiencing some of the similar feelings as a single person is feeling during the holidays. And there's lots of different feelings that come up during the holidays, depending on, you know, your past experience, um, where you are in your season of life as well. And I will have to share with you, I this will be my fifth holiday kind of season time being single. And I will be honest, it's been rough. There's been some really uh bad years, and some, you know, I tried to make things happen some years, and I can truly say this year is one of the first years I'm actually looking forward to the holidays. And, you know, some of my experience has been I have been alone on Thanksgiving, which really, really stunk and it hurt, and there was lots of emotions happening with me. But in some cases, it was my choice to be alone because maybe I decided to do a dog sit, a house sit during that time, because I've been also fairly nomadic the last uh four years, and so I actually haven't even had a place to host these holidays myself to kind of change that up. So I've been kind of at the uh, you know, the whim of other people, or just um having, you know, maybe an actual quiet holiday, depending on what I was feeling. And so I've had some, you know, I've had some really depressing times during the holidays. I've been alone. I've had some major sadness and grief. And uh, you know, it just made some feelings, other feelings I had was I was feeling unworthy and that I didn't belong anywhere. So I felt disconnected and lost. And it just presented itself and during these times because these holidays are typically when we are surrounded by family. Now that's tradition, but it doesn't have to be. And if you find yourself in this place, I'm speaking again to either my single women or empty nesters, even if you're married and you're kind of feeling a little unsure what the holidays will bring as an empty nester, this episode would be for you as well. And the first thing I want you to do is first of all acknowledge and identify those feelings that you're having. So I read through, um, I'll read them again, that I was experienced, and it varied depending on the year. You know, I went from sadness because often the holidays can also remind us of maybe a lost loved one, a lost family member, or just a lost relationship. And for me, it was a loss of a family unit uh when I got divorced. Um, but the holidays also do tend to remind me of some lost loved ones. So maybe that's also you. Maybe that's kind of the feeling you get every holiday because you're reminded of this person. Well, I'm gonna give you some uh tips on what you can do to sort of um utilize that feelings that you're having, that sadness, those memories into something positive. Um, other feelings I had, as I mentioned, was I was alone or I felt lonely. I felt disconnected or let in general that I didn't belong anywhere, um, unworthy, lost, and depressed. Um, so you know, I've had some Thanksgivings where I was I was alone. Um I I hated that feeling. I really did. And um there was a Thanksgiving where I joined my friend's family, and that felt really odd, you know, because I'm the oddball out, it's all of her family, and I'm the only single person, and it just felt weird. It was a great invite. I did get some great food, but it just didn't feel uh comforting, I guess is maybe the word I'm looking for. So um, you know, as you look at your feelings, you identify them, um, just please honor them. Know that it's okay to feel this way. And what I'd like you to do next is once you've written them down, I really want you to write them down, just like I did and listed them off to you. I want you to secondly decide maybe what you need emotionally, physically this holiday season. And you're like, well, what does this have to do with travel? Well, it does because most times during the holiday, we will travel to see family. And maybe that's something you're also planning to do. And I bring it up this early. I know we're just in October, but trust me, all the Christmas decorations are out in the stores right now. And you would need to start booking travel if this is something you are considering. Now, if you're thinking about going somewhere in the US for Thanksgiving, uh, getting flights probably is a little late for that because they have increasingly gotten more expensive. Now, I am going somewhere during Thanksgiving week. I'm so excited. It's like the first year that um I've decided to get out of town during Thanksgiving because I'm tired of being alone. And it's just not really my holiday. Um, it was actually always sort of more my ex-husband's holiday. He loved to cook, which is great. Um, but it was never really uh that meaningful to me. And so since I don't have a family to gather with, I and I haven't for this will be the fifth year, I have chosen and I wanted to do it before, and I finally just bit the bullet, said, that's it, I'm doing something for myself, and I booked a cruise during the week of Thanksgiving. Now, I did book those flights way back the end of August, so three months out tip, you know, is typically good. And I know as I've looked at prices that they have increasingly gone up during this time. So a road trip might be good during Thanksgiving, uh less expensive, or they say international travel is actually rather inexpensive during Thanksgiving here in the U.S. So if you're from the U.S. and you want to do some international travel, um, it's supposedly very affordable during Thanksgiving week. Um, but you can still book flights for Christmas, which I also plan to be somewhere at Christmas with my family, extended family that is, um, because again, I don't want to be alone. So I made that decision, I made that choice, and that might be where you are at, and you know, like for example, maybe you know that you feel alone and or you're gonna be lonely, but you don't want to feel that way, then make an initiative to be with other people. So deciding what you need, maybe you do want to be alone, and I will have to say, just being alone can't it can lead to feeling lonely, but being alone does not mean you are automatically lonely. Okay, sometimes being alone is a good thing, so you need to decide if that's the feelings you're having and you're not sure that you want to be alone, and maybe you feel like, okay, I'm really down and depressed this season. I think I need to be around people so I don't get worse. Then make an appointment to, you know, find the group, find somebody to be around during the holidays. Maybe you have some other girlfriends that are also going to be alone, or maybe you feel okay asking a friend if you can join their family dinner, and that's okay. They may, they may not even realize. Um, so you know, put yourself out there, especially if you are feeling um depressed or lonely and you don't want to go to that place, especially during the holidays. You're feeling maybe sad about a loved one during this this time of season. I find it so cathartic to do something in memory of maybe a lost one. I'll give you a few examples. Um I did lose my mother um a long time ago, and I do recall, I believe it was that first Christmas after she had passed, one of she loved um birds and bird feeders, and we had for her funeral, had set up some beautifully painted bird houses, and at Christmas time we ended up kind of gifting those to some special people um in her life, and that was so uh it was just heartwarming, even from my perspective, as sort of that giver, and witnessing um the tears and just the love from other people, the memory that they are now able to actually physically hold on to. Uh, similarly, when my grandmother passed again, she loved birds and she collected these um ceramic birds. And after she passed, I do recall um everybody in the family really um was given a bird uh as a reminder of my grandmother. And I've heard other things, you know, uh maybe in memory of somebody uh doing something that they enjoyed doing during the holidays, maybe they were um a serving or giving type, and so you therefore do the same uh in memory of them during that time. So if that's maybe your case, you're facing the holidays and you've lost a loved one, you've lost a relationship, you've lost family, that do something positive in memory of them. So instead of focusing on, you know, oh my gosh, they're not here, how could you create an atmosphere that reminds you of them in a very positive, heartwarming way? And I highly recommend that. So if that's you, I remember those first few years, that was super important for us as a family to acknowledge. And um I personally did that uh more for myself. Um, you know, soon after I got divorced, I had during my marriage, I had collected nutcrackers, speaking of Christmas. And I, because I'm a nomad, I really haven't had the opportunity to display them. And each of those nutcrackers, even though it was bought as a family, uh reminded me of certain people in my extended family. So a few Christmases ago, I actually gifted each of my you know extended family members, I had that many, yes, um, a nutcracker that sort of reminded me of them. And I gave my children um a few and I kept two of my own. And so that could be something too you do sort of in memory of for me, it was in kind of an acknowledgement of the loss of um my you know from my divorce, the loss of sort of that family union, but it gave me the opportunity to sort of give instead of sort of wallowing in that. So um again, one identified and identify your feelings, write them down. Number two, decide what you need emotionally or physically based on that list. And then three, is I'm I'm kind of discussing how can we counter those pending feelings around the holidays of being alone. As I mentioned, just because you're alone doesn't mean you have you have to be lonely. Um, doing something, as I said, to combat the sadness, doing uh something to combat the alone or loneliness by taking that step and maybe finding a group of people to join. Maybe there's other single people in your if you live in an apartment complex or if you are traveling, there could be, you know, just joining uh some group of people during that time. Maybe they don't even celebrate. Obviously, only Americans celebrate uh Thanksgiving. So if you're traveling during Thanksgiving, um just joining other groups on that day, uh, probably creating new memories, obviously, will happen. And it's just gonna be a different memory for you on that holiday, which I highly recommend creating new memories and positive memories on those holidays, addressing each emotion as I have discussed. Um so I decided since I did not want to feel alone again or disconnected, because that was that's kind of been a big thing, just feeling like the oddball out. Um, so maybe a travel during the holidays is what you need. And I highly encourage that because this again is creating new memories around that holiday time that maybe at this point in your life doesn't feel comfortable, and you are not wanting to be, you know, have old memories brought up, and so you're gonna create new ones through travel. You're gonna have some positive memories, energy, new energy coming into your life. This may even set the stage for your future holidays. I hate to say that. You mean you might get so um inspired and addicted really to that idea of traveling during these time frames that maybe that will become your new norm. And I highly encourage if you are single, empty nester, and you are struggling with these pending holidays, I want to encourage you. Travel can be not just a means to uh to escape, maybe these traditional family, you know, or whatever traditional ideas you have of the holidays that you might be uh not fond of because of some past hurts or emotions that you're dealing with, then travel can be that healing vehicle to get you to that place. And I am so looking forward to my trip because I know it's gonna start to create new memories. I think it's gonna be a new thing for me every Thanksgiving. I think I might keep this as a as my tradition moving forward. And then for me at Christmas time, because it is important for me to be with family, and I don't have really a place to gather, and my children here, they are local, but they're likely going to be spending it with their father and their grandparents and aunt uncle from my ex-husband side, which is great. I love it, and um, it's just awkward for me. So I've chosen uh to go see my family um in another state and spend some time with them during the holiday season and you know just reconnect because I I do love my family. I know that's not always the case for everybody, and so maybe you need to find um your own created family. It doesn't have to be blood family, right? We often find some of these uh friends that you know we might kind of call sisters, even though they're not blood sisters, but you feel so connected to them, and maybe this is your opportunity to create that, you know, maybe you do something with them during the holidays to create sort of that closer bond, even and that your own family bond there during the holidays. Well, sisters, I know, I know for a fact I've been there and still are there that the holidays are a very challenging time for us single women, and especially, I feel like especially the us as older women or midlife women, we're kind of in that just weird kind of phase. Um, I want to encourage you to create your own memories around the holidays and get out there and have those adventures and don't hold back because this is your opportunity now to do that. And if you're still needing some guidance on, you know, what you should do, I am available. I do one-on-one travel coaching. You can book a discovery call with me or even go to my website to find out more about my program. But I still would love to hear from you, and I would love to even see if you, you know, you go somewhere different for all the holidays. I'll be posting a little bit of mine in my Facebook group once I, you know, I'm um on my cruise, by the way. So I am looking forward to it, and I look forward to hearing about positive stories of how you have changed a holiday, a dreaded holiday, into something amazing.