
When I was younger (up until my 30s, really), I associated being alone with being lonely. Why would I even consider going out to dinner by myself, let alone taking a trip by myself, when I had great friends, my family, a boyfriend? Traveling alone sounded sad, depressing . . . something that would be a last resort vs. something I would want to do!
The turning point came when I was 32. My live-in boyfriend and I split up and I moved out. Back then, his friends were my friends, his interests were my interests. The breakup wasn’t just a loss of the relationship, but also of our friend group, the activities we’d do together, the trips we would take. When I recovered from the shock of it all, my life felt like a blank slate. Of course I had my job and my girlfriends and a few other constants, but otherwise? In a way, my life had been wiped clean. This felt scary, but also exciting: I could really spread my wings and make my life mine.
Once I was settled in my new apartment, I decided to book a solo trip. I’d only traveled by myself once—to Greece, when I was between jobs in my 20s and none of my friends could join—but something in my gut was telling me that a solitary beach vacation was exactly what I needed. I was nervous, but I cast my jitters away and booked a room at the Coqui Coqui in Tulum (it closed in 2016—I miss it so much). The trip would be a way for me to reset, think, get away from New York, get reacquainted with myself. Leading up to the trip, I wasn’t really sure what to expect. Would I be bored? Lonely? Would it make the breakup blues even worse? And how would I entertain myself? I packed a lot of books.
The trip did have its low moments. I remember being frazzled, trying to navigate the airport and find ground transportation. I remember being scared (there was a robbery at the front desk one night; I just hunkered down in my room and hid). But mostly, I remember how good it felt.
The feeling of not being beholden to anyone or anything. Getting to do exactly what I wanted (and some days, that meant nothing!) without any pressure or worrying that I was letting someone else down. The moment I stepped outside of the hotel, I knew I had done the right thing. I still remember how my feet felt, slipping into the powdery white sand. I breathed in the salty air and I swear, my shoulders instantly lowered a solid two inches. I plopped down onto a chaise longue and did not leave it. Waiters came and went, bringing me water, coffee, breakfast, lunch. I read a book and a half that first day. I took reading breaks to swim. Every night, I walked to dinner, bringing my book along for company. And then, I would come home and read some more. I loved the quietness, the freedom.
In hindsight, that trip is when I got back to feeling like myself again. It’s also when I rediscovered my love of reading. I had always been a big reader, but when I lived with my ex, it fell by the wayside as we entertained often and watched a lot of TV together. Gone Girl had just come out; I fell in love with thrillers. (Not much has changed!)
From then on out, I traveled by myself quite a bit, going to Europe, even Asia. Asia was by accident—
had a family emergency, so I was on my own (but I loved every minute I spent tromping through Bangkok, Cambodia, and Koh Samui).Now, it’s been a little over five years since my last solo trip and I’ve been feeling the itch again. Traveling solo is tricky in any relationship, but trickier in a long-distance relationship. I love being home, so most of my travel time is spent visiting my boyfriend unless I plan something far in advance. I don’t travel enough with my girlfriends, much less with just myself.
In just over a week, I am heading to France for my creative retreat. What I’m looking forward to—maybe even more than the retreat itself—is that I’m bookending the trip with a night in Paris on each side. Just the idea of a night alone in a fancy hotel room and puttering around one of my favorite cities has me positively giddy. Shopping, meandering . . . having a book date at a sidewalk cafe . . . spending as much time as I want in the pharmacy shopping for skincare and perfume . . . stopping into boutiques as the instinct strikes . . . I cannot wait. I haven’t planned much aside from hotel reservations (and David Hockney at the Fondation Louis Vuitton). This trip won’t be about going to the best restaurants or getting Instagram-worthy moments. It will be about seeing where the days take me.
Here’s what I love to do when traveling solo:
Take myself on a museum date. Sometimes I’ll do the guided audio tour, other times I will just roam and listen to music.
Post up at a restaurant bar with a good book. Sometimes I’ll read the whole time; other times, I find myself getting chatty with the bartender (always the best way to get off-the-beaten-path recommendations).
Journal. Besides a book, I also bring my notepad. I have some of my best ideas (or aha moments) when I am traveling alone.
Just walk and wander. This sounds trite but it’s true: Nothing is better than getting lost in a new city. And thanks to Google Maps I can’t get too lost. My favorite time to do this is early in the morning. Grab a coffee and just stroll!
Go to bed early with room service and a movie. I know, maybe this is lame to some, but if I have been walking around all day and I am staying somewhere nice, I love coming home, renting a movie, and tucking into bed with good food and a nice glass of wine. I never eat in bed at home but it’s OK on vacation!
People-watch. Europe, in particular, is great for this. Settle in with a glass of wine and a snack and just enjoy the fashion, imagining strangers’ lives, eavesdropping on other people’s conversations.
Do you like to travel alone? What are your favorite solo destinations?

Tropical print overload! A super fun banana dress, and all of the fronds, flowers, and fruity pieces.
My three favorite nail polishes.
Vintage Finds for the home — Carly hit it out of the park with this one!
My summer uniform. Pretty maxi dresses and dad sandals are the perfect easy look for this hot, humid weather.
A review of Ormaie’s Les Brumes fragrance: it smells like an orange grove!
It was a big week of reading; I was feeling a little under the weather and had a lot of cozy time to read.
I finished reading Next to Heaven, by James Frey. I know he’s controversial. But I enjoyed this (maybe “enjoy” is the wrong word, it was dark and twisty and kept me on my toes). The plot centers around a wealthy town in Connecticut. Think 1% of the 1%. I think I liked it because it felt like the perfect chaser to Your Friends and Neighbors (I have a TV hangover, missing that!). Two women decide to have a swingers party, and the group dynamics are forever changed. Also, there’s a murder! (Order on Bookshop.org or Amazon)
Next up was Jill Is Not Happy, by Kaira Rouda. I will save you on this one. Skip it; it’s just not good. It is about a married couple, keeping secrets from each other. Jack is unhappy and is only with his wife because of shared history and secrets. But Jill has secrets of her own. The writing is over the top and soapy, I kept thinking it was going to go somewhere (it’s very suspenseful), but the ending was super lame. Not my cup of tea! (Order on Bookshop.org or Amazon)
After that, I read Park Avenue by Renée Ahdieh. This is about a young, ambitious lawyer (Jia) who gets the career opportunity of a lifetime working with the Park family. It was described to me as a Korean Beauty Succession, which obviously piqued my interest. The patriarch of the family has left his dying wife. His three children are convinced that he’s hiding the bulk of the family fortune and hire Jia to help them find it. I liked this. Not a love, but a solid like. (Order on Bookshop.org or Amazon)
My current read is Notes on Infinity. I am just over a hundred pages in and am enjoying it so far. It’s about two young scientists who drop out of Harvard to create a groundbreaking anti-aging drug. I’m getting Tomorrow and Tomorrow and Tomororow vibes a little bit (the platonic friendship + building something together) and I like the academic setting. More to come next week!
On Audible, I am still listening to Original Sin: President Biden's Decline, Its Cover-Up, and His Disastrous Choice to Run Again. It’s a hard one. I feel like it’s important to listen to it and understand what went wrong, but it’s also quite depressing. To be totally honest with you, I can’t wait for it to be over (and to listen to something a little more upbeat and happy).
I absolutely adore traveling alone—maybe even more now, as a mom. Grace nailed it: that feeling of being beholden to no one, of letting the day unfold in a hundred possible directions, with only you as its arbiter.
These days, I can’t often swing a full solo trip (I’m incandescently jealous of your creative retreat, Grace!). But for anyone in a similar season, craving just a sliver of that same magic—a quiet night dining solo at the bar hits some of the same notes for me. Small freedom. Big joy.
Love this post and can relate a bit. As I have often said,I am prob. much older than the majority of your readers. My husband does not enjoy travel (and 2 grown sons who travel with their spouses/no daughters) and I LOVE to see new places. He did go to Italy for a 35th wedding anniversary and although he said he enjoyed it no interest in other trips. After that, I gathered up all my courage and booked a trip to Provence. It was so empowering as other posters have said; to do what you want when you want...to make yourself happy. Last fall I traveled with the same tour group to Wales and London. I have found that on the tours with this company most people are not single travelers and although friendly ...want time with the people they came with. I am not sure I would do another international trip alone (at my age) but def. within the states.