A Single Woman on Holiday: 6 Must Do’s for Meeting Yourself

We don’t know what we’ve got till it’s gone. This is true for so many things after divorce, but in this case, I am referring to family vacations, those idealized holidays we took with our children and our husband. Those rare two weeks, where away from the home front, and the grind of our jobs, we stepped into an alternative reality, one where we were not responsible to a boss or our employees, nor for making sure the children were fed and had done their homework. That special place where relieved of daily responsibilities and expectations, we could enjoy the adventure and peace of being with each other. Now divorced, that’s how we remember those times, with nostalgia and grief, especially when we are facing the prospect of more aloneness, being a single woman on holiday.

Holidays epitomized who I was, my achievements, entitlements and privilege

Like many of my peers who started careers in the 90s, I was a professional who worked long, hard office hours. We did not believe in a work-life balance in those days — we’d never heard of such a thing! We had been told instead that as women, we could and should be able to do everything. So, if we had office jobs, we might have outsourced to grandparents or nannies the taking of kids to school, or even family dinner time or bedtime routines. It was worth it, or so I told myself. In exchange for such sacrifices, we had amazing family vacations. In fact, I felt entitled to spectacular vacations because I worked so hard every other day of the year.

They are what I lived for. Each year I organized two weeks of pure family heaven in a lovely European destination. It might have been coastal France, the mountains of Italy, or the lakes of Austria and Germany. Vacations were a chance to connect with European culture, get compliments for speaking a foreign language, and to step into a fairy tale where I pretended to be French or Italian. We traveled together then even when the boys were breast-fed infants. (Yes, back at work, I had pumped at the office.) We rented cars, stayed in quaint villages, slept at family-run B&B’s, and along the way, discovered hidden gems unmentioned in the guidebooks. As an event organizer at work, I was very good at making sure our family trips were off the charts.

Holidays were the chance to be the happy family I dreamed about

We had time for the kids, we enjoyed ourselves, our intimate life was good, and there were no work distractions. Once we got settled into our foreign routine of vacationing, my Ex would be in a good mood. That’s why these vacation times became increasingly important. They became a time to parade my success and what we should be. I was realizing my dream for the world. I was a married woman of means with two beautiful blond boys, we were a picture-perfect family.

But once that family picture fell apart, the holidays did too.

Divorce, redundancy, and COVID ended my pleasure trips

Two and a half years ago my divorce happened. It was followed shortly thereafter by the COVID pandemic. And then my lay off due to redundancy occurred. “What is redundancy?” I asked, stunned at the time. Redundancy is the process, I was told, “whereby employees are let go due to circumstances unrelated to job performance.”

A BIG DEAL is what is meant for me. In one fell swoop, I no longer had my full family to travel with, France was no longer accessible by air, and I couldn’t afford any of it anyway. The whole thing was a blow to my understanding of social success and quality time. What had I been working so hard for anyway?

When my (now extended) vacation time approached, I was seriously anxious about what I would do, what I could do as a divorced, single woman on holiday.

What comes with you as you enter your new chapter as a newly divorced woman? Read “Life After Divorce: The Grief You Didn’t Count On.”

Cautiously finding my new way as a single woman on holiday

As pandemic rules eased, I avoided being alone. I started taking trips with one son at a time. I discovered that these trips were cheaper, easier to organize, and limited any sibling rivalry. As well it gave me important personal time with each of my boys.

Elsewhere, I took several short breaks with girlfriends. I loved these! We girls enjoyed our spas and gallery trips and having a glass of fizz at lunch. I even traveled with a couple that I have known for decades but stopped it as it triggered my sadness. I saw how caring a husband can be to his wife when mine never was.

These trips, while pleasant, weren’t transformative. They basically followed the same process I was familiar with: as a single woman, I coordinated with others and adapted my time, needs, ideas, and budget to accommodate others, especially during the holidays.

What do they not tell you about getting divorced when you are Middle-Aged? Check out “The Truth About Starting Over After Divorce at 45.”

Solo trips challenge you to show up alone

This past summer I booked a flight and rented an apartment all on my own. I went to the Baltic Sea for four days. And as a result of this experience, I’d like to share my single travel tips with you, my Sisters, so you can be encouraged and prepared for similar adventures when you travel as a single woman on holiday.

As soon as I arrived at my destination, with my feet hitting the airport floor, I asked myself… 

What the hell am I doing here?

How dare I go on holiday without purpose! 

During my many years of marriage and childrearing, I had fallen out of practice of caring for myself. In a lot of cultures, communities, and families, there’s an explicit understanding that after divorce (in fact, at all times), we need to put children first. We need to economize. Even as I write this, I hear the words of an elderly relative who told me, “We never took trips on our own and you shouldn’t either.” All these messages of what we should and should not do can lead to feelings of guilt and shame. Those messages are bound to bubble up and shout as we embark on our single woman adventure. And mine did for sure.

Guilt trip as part of the voyage

One night I literally woke up because of this guilt and shame. I searched my brain for reasons. Did I overeat? Did I drink too much? That usually makes me ashamed. But no.  I felt guilty because I was enjoying myself without any mission. I was just sunbathing, swimming, eating, browsing secondhand and antique shops, and meandering through souvenir booths.

If like myself you come from a strict upbringing, if you were used to hearing “you should be ashamed of yourself” or “you should think of others first” be prepared to feel guilty during your first solo vacation. Because you won’t be hiding behind someone else’s joy, the joy you discover will be all yours.

As I considered these messages in my psyche, trying to hold me back, I started to realize there were also other messages coming from other voices. And these messages I preferred. They came from sources I had read, sources that seemed to honor me as a modern single woman, a human being who had choices as to which voices I would listen to. These new voices told me divorce recovery and rebuilding my life would require that I sit with this discomfort of getting to know myself. And I would only be able to do that if I were alone.

Consider that, dear Sister. And you might discover that being with yourself through thick and thin might actually become a new life value for you, too.

Tip 1: Plan a short trip to lessen anxiety 

If you are new to traveling on your own, don’t book an entire 2 weeks. Even if you end up really liking it as I did, you can be ridden with anxiety in preparation. Will you be lonely? Will you be bored? So, start short and extend the experience next year.

Tip 2: It’s not THAT lonely

I took a 4-day trip and was surprised at how I wasn’t lonely. In the beginning, I felt compelled to share my experiences and photos with girlfriends and family. Then I left my phone off for longer periods. I noticed that I haven’t done a single social media post.

Holidays offer quite a lot of interaction. Kids, dogs, cats, waiters, shop assistants. You talk to them. You hear people’s conversations. People watching makes you feel quite involved. And if you mention that you are traveling alone, people are even more comfortable talking with you and often want to help you.

Tip 3: Be prepared to learn new things about yourself

Remember the time when you fell in love and were thrilled to find out any novel thing about your new beau? Their taste in food, the band they loved, how they slept, how much time they spent in the shower? Or, when your kids, now older, shock you with their own opinion? These discoveries are all new and exhilarating!

Spending multiple days on your own without counting on, or distracted by anyone else is an amazing journey of discoveries, too. But they’re all about you.

During my solo trip I realized that I like to get up early as opposed to having long sleep-ins. I headed to the beach to do yoga, power walk and swim until 10 am. Then I had breakfast in a café. I liked to wear a dress at breakfast and not my yoga pants so I always packed a little beach dress in my backpack. I’d slip it on before arriving at the café, to almost mark a different part of my day. Then I might stroll or wander into a museum or shop. Later, I was happy to have takeout for dinner in my rented apartment whereas previously going out in the evening was very important for me.

Finding your sexy as a single woman on holiday

As I spent time on the seaside, swimming, exercising and walking, I gained muscle tone, a tan and confidence. I walked around in my swimsuit or little beach dress, almost laughing at myself and how I’d been earlier that spring, quite certain I’d never bare my upper arms again. 

I felt a certain freedom, I reconnected with my 19-year-old self. I remembered how I spent a summer in France living with a French family. I was young, good-looking, full of hope. I feel similar now. For the first time since divorce, I remembered that I had a life before marriage. I realized that I had experience of being on my own and minding my own time.

If you wonder where IT went, don’t worry, it’s there. Check out “Finding Your Sexy Again After Divorce.” 

Tip 4: Disappointment is possible

As I reconnected with my 19-year-old self, I started noticing men and became ready for flirting for the first time since divorced. I assumed that when I was ready to flirt, men would reciprocate just like when I was young. 

But I was disappointed.

It didn’t happen. My first reaction was to get upset. I blamed my age. Who would want to hit on a 46-year-old anyway? Similar to how I paraded my family on holidays in the Old Days as a sign of personal success, I was about to see the lack of male attention as a personal failure.

I was sad and disappointed and thought for a moment that these emotions would dominate my trip. But they didn’t.

Tip 5: Give yourself time

I realized that it just works differently when you are 46. I need to accept that I will not find my next boyfriend during my first holiday trip as a single woman. Like all other things related to divorce, we need the space to build new strategies and allow ourselves time.

On my way back home, the airline upgraded me to business class. After a glass of wine, I allowed myself to start a conversation with a man in the seat next to me. We chatted, giggled, and almost flirted.

As my plane was landing, I wrote down my last tip on solo traveling.

Tip 6: Plan for regular solo trips from now on.



Anna Ivanova-Galitsina is a communications and storytelling expert living in Moscow, Russia. She is a regular writer for SAS for Women. She can be reached on 

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*We support same-sex marriages. For the sake of simplicity in this article, however, we refer to your spouse as your “husband” or a “he.”

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