The Solo Trips You Take at Every Stage of Life

And the Woman You Become Along the Way

Blow the Bonus and Book the Flight

Life stage: 20s, zero responsibilities, full passport — Trip: Europe with a carry-on and no exit strategy. In my twenties, I quit my Wall Street job the second my bonus hit. I had no responsibilities and no interest in collecting any. I booked a one-way ticket to Europe and stayed gone until the money ran out. Then I came back, took another job, and did it again.

I never stayed in hostels. I still wanted clean sheets and a decent cappuccino. But I traveled without plans. Spain one week, Italy the next, maybe France if the mood hit. I said yes to things simply because I could. That kind of freedom is rare. If you ever get it, use it.

The Mid‑Parenting Interlude: Escape, But Make It Polite

Life stage: Kids, career, emotional triage — Trip: Wellness retreat with structure and a wine list. There was a stretch of years when I did not want to explore anything. I just needed to stop. I wanted someone else to plan my days, bring me food, and hand me a schedule that I could ignore without judgment.

The BodyHoliday in St. Lucia became my default. Spa at ten, Pilates at noon, cocktail at five, silence all day. There were other solo travelers. There were just enough conversations to feel human, but never enough to drain me. This kind of trip is not about growth. It is about space.

The Divorce Era: Strong Legs, Stronger Spine

Life stage: The unraveling — Trip: Women’s cycling trip in Provence, hiking to Machu Picchu. After my divorce, I did not want to heal. I wanted motion. I joined a women’s cycling trip through Provence with Backroads. We rode through lavender fields, past vineyards, up hills I cursed with every pedal stroke. I had dinner with strangers who did not ask questions. That trip helped me put myself back together, without talking about anything.

Later I hiked to Machu Picchu. The altitude took my breath. So did the view. I stood there, filthy and blistered, and felt stronger than I had in years. This kind of solo travel is not reflective. It is corrective.

The Midlife Audacity Trip: You Go Because You Can

Life stage: Early 50s, nothing to prove, everything still ahead — Trip: Expedition to the Galápagos. By my fifties, I had stopped waiting. I wanted to go to the Galápagos and that was the reason. The ship was elegant. The days were simple. I snorkeled with sea lions and stood inches from blue-footed boobies. The air was clean. The silence was whole.

No one needed me to document it. I did not post about it. I did not write a review. I came home with a full journal and an even fuller sense of wonder. That was enough.

The Exit Strategy That Did Not Stick

Life stage: Post-company sale, space to breathe, not ready to disappear — Trip: Soft sabbatical in Bali. After I sold the company, everyone asked what I would do next. I did not know. So I went to Bali. I stayed in Ubud and walked a lot. I tried sound baths I did not believe in and cried anyway. I stopped explaining myself. No one asked what I did. No one cared. That made all the difference.

This was not a trip about doing. It was about being. It let me fall back into myself and stay there until something new surfaced.

The Reinvention Years: Build What You Wish Existed

Life stage: Act Two, high-functioning clarity, no time to waste — Trip: Expedition yachts, remote islands, and something entirely new. This chapter feels different. I am not retreating. I am building.

I started traveling on expedition ships again. Not the rustic kind. The kind that serve perfect wine after a day on a glacier. The kind with real guides, clean design, and just enough guests to disappear when you want to. I also started building the kind of trip I could never find—luxury wellness that does not take itself too seriously. I call it Unwellness. It includes biohacking, Oura Rings, spa treatments, and proper martinis. It is the most honest thing I have ever created.

Ready When You Are

You do not need a reason to travel alone. You need a window. A moment. A version of yourself that still wants more.

If you know you are ready but are not sure where to go next, that is where I come in.

Check my availability here.