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 identified with solo impulsive travel before I knew who I was. If you're feeling that too, begin your spontaneous escape with a solo travel trip.

I never stayed in hostels. I still wanted clean sheets and a decent cappuccino. But I traveled without plans…

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 wanted a massage, room service, and nobody to ask me what’s for dinner. That’s why midlife wellness retreats are the ideal escape hatch.

Somewhere around year twelve of parenting, a certain type of silence feels better than conversation. You don’t want to be around strangers — but you want to be around people. You want to share a meal without carrying it from the kitchen. You want to go to yoga without being the one who suggested it.

The Divorce Era: Strong Legs, Stronger Spine

Life stage: The unraveling — Trip: Women’s cycling trip in Provence, hiking to Machu Picchu. This isn’t healing. It’s reclaiming. Sweat, solo time, and solo travel can reset you—even if you left alone. Start your reset with a solo travel adventure or a physical challenge in Europe or beyond.

The second I was free, I joined that cycling trip. I got stronger every day, learned to drink wine at lunch, and laughed with strangers until I remembered how.

The Midlife Audacity Trip: You Go Because You Can

Life stage: Early 50s, nothing to prove, everything still ahead — Trip: Expedition to the Galápagos. Still curious, still unapologetic. That’s how you know you’re midlife, not middling. If you want nature, depth, and bragging rights, consider a true expedition experience.

By my fifties, I had stopped waiting for permission. I took the good camera. I took the rubber boots. I took the private flight and sat up front.

The Exit Strategy That Did Not Stick

Life stage: Post-company sale, space to breathe, not ready to disappear — Trip: Soft sabbatical in Bali. This is when you think you’ve retired. You haven’t. You’re just in hiding. Hide well. Hide where everything still moves, just not urgently. Hide in a villa that doesn’t ask you for anything.

After I sold the company, I thought I’d travel for a year. I lasted four weeks before dreaming up something new. That’s the trick of soft sabbaticals — they give you just enough space to remember how your brain works.

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. I needed a journey designed by someone who already knew the route. So I made it. You can too. Try an expedition cruise with bite or check out my signature retreat blend at Wellness + Exploration.

This chapter feels different. I say no faster. I don’t need to “find myself” — I already like her. And I’ll book the yacht to prove it.

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.