On Traveling Alone

Happy New Year (at the risk of infuriating Larry David, I’m saying it to you… because I can! And because I love a beginning! You can’t steal my joy!).

Before we get to today’s story, a few fun things happening lately in the Long Weekend world.

YOLO Journal asked me to write about my time at Esalen (PINCH ME). I also got to gush to YOLO about my favorite city spa that my friend Cate designed (we met working together to develop the Willowbrook Spa at The Lake House on Canandaigua). We have a new project that’s starting to slowly take shape… a beautiful independent hotel rebrand & reposition on Whidbey Island. We’re about to start construction, and last week we flipped off the old site, and are a full virtual + IRL ‘work in progress’ before the re-opening this summer. (here’s a little peek at the new look & feel on our temporary landing page).

Now, the main event today is two-fold.

I’ve been wanting to write more around my thoughts and feelings on solo travel, and I had a fun chat with the lovely Emma Saadi Mejlstrup of Le Souvenir (you know I love a good souvenir)about her feelings on traveling solo, (Long Weekend’s first interview!!).

Andiamo!

This newsletter cracked open a window into why I’m drawn to the challenge, and quiet adventure, of traveling solo. It inspired (at least) two friends to take off on their own solo journeys: one to Japan, the other to Ischia. Hearing that made me feel deeply honored, and also reinforced how important it is to have a dialogue on what it’s totally normal - exceptional even - to travel someplace alone.

A sense of adventure or curiosity doesn’t have to wait for a partner or a friend to accompany you. Sometimes, we need to set out into the world on our own.

Now, I’m not saying you need to go on a solo safari, or a romantic Amalfi Coast adventure alone. (Though I have done the latter, and may I note, iconic honeymoon destinations can be tricky to arrive at solo, depending on your emotional state.)

How it started

I came to solo travel accidentally. I was recently divorced, facing a holiday alone that I didn’t quite know what to do with. Yes, I had friends who would have hosted me. Yes, I could have made an impromptu trip home. But some small part of me spoke up and asked to be anywhere but where I was.

I was adrift. I didn’t know where to land. I wasn’t ready to confront my confusion.

I wanted to step into a portal. That’s how I ended up alone for a long weekend in Paris. (perhaps I’ll tell that story sometime soon, I wrote a draft with Ruthie, and have been working up the courage to share)

Why travel solo at all?

Well, wherever you go, there you are.

It’s a way to check in. To be with yourself in a different setting. To push gently at an edge. To discover courage or perspective you didn’t know you had. I’m consistently surprised by what comes up when I’m on the road alone. With what gets quieter, and what finally gets loud enough to hear.

Courage is contagious. Never underestimate the ripple effect of doing something brave, of stepping outside your comfort zone. You may find it unlocks something in your day-to-day life you couldn’t quite reach before. Or gives you permission to listen to a quiet yearning you’d been ignoring. Or, best of all, inspires someone around you to reach for higher heights too.

This feels a little silly to admit, but driving solo in countless countries (especially down a narrow, one-lane road over a mountain range in rural Ireland) is something I never imagined being able to do. It put the feeling of courage deep into my core.

Over the holidays, feelings carefree bumping down a dirt road in Todos Santos, I caught myself smiling. The simple act reminded me: we can do so much more than we believe is possible.

Find a way that works for you

If you’re curious… there are a few ways I drop into solo travel.

Sometimes it’s for fun. I’m a seeker. I love movement, novelty, and pleasure. I make time for it. I prioritize fun, even if it’s just a weekend away in Laguna or Carmel when I need a shift.

Sometimes it’s for healing. When I’m at a breaking point and need to change momentum. To create a quantum shift.

And sometimes it’s for expansion. When I’m ready to stretch. To take a trip that overflows the limits I once thought possible.

I believe you make solo travel work for you.

It can be a small weekend an hour from home.
It can start with a solo dinner.
It can be a single day alone on your next group trip (planned just for you) then shared over dinner that night.

It can be a retreat or group trip where you don’t know anyone, but you get to meet everyone.

Go somewhere that’s fun to be alone.

For me, that place is reliably Paris. A city where noticing and observing is a way of life. Dinner solo is far more enjoyable when you’re seated at an outdoor café, watching the world roll by.

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Phone a friend

I realized I didn’t want this to stay a monologue.

Solo travel is deeply personal, but it’s also collective, shaped by how others experience solitude, courage, and noticing.

Recently, I connected with Emma, over our mutual love of travel and observation. Almost immediately, I felt a kindred spirit. She’s someone who wants to feel a place, not just see it. To soak it in. To luxuriate. To let the spirit of a place seep into the body and into memory.

Her writing explores the inner life of travel, what solitude reveals, what slowness restores, and how being alone can become something rich rather than something to avoid. Reading her work felt like a continuation of the questions I’d been circling around.

I asked Emma a few of these questions, and was deeply inspired by the conversation… I hope you are too.

What does being alone in a place make possible that traveling with others doesn’t?

I think it’s a chance to truly get to connect with a place and let it tap into your own creativity. Because you can spend your time, money, energy, and so on, however you want, you never really have to negotiate your curiosity.

How do you notice differently when no one is waiting on you?

I’ve found that traveling alone is one of those rare moments when I’m truly able to observe my surroundings and connect with my presence. That’s when I start noticing the specific ‘textures’ of a place, like the weight of the air in an ancient church, or how the sun reflects off the water in a fountain.

For someone curious but hesitant, what’s a gentle first step into solo time?

Try to earmark a few hours to explore on your own when you’re traveling with others. I think that’s a gentle first step to see how you feel being alone in an unfamiliar setting, while still having the comfort of knowing you’ll reunite with your people later in the day. If you don’t have any trips lined up right now, I’d say to make a habit of going on solo dates that include some element of change in your own city. That could be seeing a play at a theatre you’ve never been to, or visiting a museum with a new exhibition you’ve been curious about. :)

Is there a place you return to alone, again and again—and why?

I used to travel to New York City alone all the time until I eventually met my husband there. I loved that electric feeling NYC has, and the fact that, despite traveling solo, I never felt alone in the city.

What has surprised you about being alone on the road?

How many aspects of your personality are actually just reactions to your daily responsibilities and the people you interact with regularly… That’s not necessarily a bad thing! But when you’re alone for an extended period of time, away from the life you’ve established at home, you suddenly realize how much more there is to being you!

How do you let a place speak to you when you’re alone?

I like to people-watch at a local bar or coffee shop. I’m also a big fan of visiting flea markets and vintage shops. Seeing the things locals are selling that previously served purposes in their lives tells me a lot about a place and the people who live there.

Was there a moment when you almost didn’t go? What helped you go anyway?

Yes! On one of my first solo trips to New York, I was starting to feel nervous about being alone all the way across the ocean, but one of my closest friends convinced me to go. She told me I was beaming with excitement whenever I mentioned the trip. That was exactly the kind of thing I needed to hear in that particular moment. It made me realize that, by not going, I’d be letting my anxiety rob me of an amazing experience!

After our conversation, I kept thinking about how often we wait. For the right moment, the right companion, the right version of ourselves.

What would life be like if we didn’t wait?

Maybe going alone isn’t about bravery at all. Maybe it’s about listening, and knowing when to act (even if you don’t feel ready).

Together, we hope you take this as permission—to dream, to wonder, and to wander solo if you want!