From Giggling Through Cairo to Leading 30+ Solo Travel Retreats

You probably have a definition of solo travel in your head, and I’d be willing to bet that definition is part of what’s keeping you from going on that trip. If solo means you handle every unknown by yourself, eat every meal in silence, never have anyone to call on, of course you’re not booking. That’s not a definition that invites you in.

When I sat down with Gina Cambridge for this episode, that was the first thing we landed on. Gina is an ICF certified travel coach and the founder of Wanderlust Solo Women Tours. She has led over 30 solo travel retreats and tours across destinations like New Zealand, Bali, and Cuba, and she works mostly with women on their first solo trip. Her whole business sits in the gap between the definition of solo travel a lot of women are walking around with and what it can actually look like. Our conversation went from a hostel bunk bed, to Cairo traffic, to a French restaurant in Strasbourg, and back around to your phone.

In this episode:

  • Group tours that still count as solo
  • Snoring, single rooms, and matchmaking
  • The bunk bed that led to Bali
  • Lunch with the phone put away
  • Cairo, giggling, and going alone
  • The family beach day and permission

If you hop on a plane by yourself, even if you join a group tour, to me it’s still solo travel.

Gina Cambridge

What if solo travel retreats are still solo travel?

Gina was clear about this from the start. For her, solo travel includes joining a group when you don’t know the country yet. You hop on the plane by yourself. You arrive without a partner. You make your own way to the hotel. The group is a blanket of support around you while you figure out the place. After a week, you have the choice of completely free time on your own.

She is specific about what makes a group tour worth it. Personally, she prefers smaller groups, under sixteen people, companies with no single supplements, and an ethos around sustainability and local communities.

As a host, she meets every guest before the trip and matchmakes the roommates. (Yes, including the snoring conversation, which she brings up before the trip on purpose because she cares about the experience of every guest.)

What does “ready” actually mean?

Women who haven’t taken a solo trip yet think they’re not ready, and women who took one twenty years ago think they’re not ready for whatever the next thing is. Gina’s answer was direct:

  • travel with no expectations, then you’re never disappointed.
  • Trust your common sense and your intuition.
  • Don’t go down the rabbit holes online.

And she reminds us that women manage so many things in our day-to-day life already, and those skills come with you on the plane.

I’ve talked about this before in the never feel ready to travel alone episode, and Gina basically said it from her side: confidence is not the prerequisite. Confidence is the thing you build by doing it. She compared it to a muscle you train. You go on a trip without much confidence, you come back with a little more, and the next one starts from there.

What about safety when traveling alone?

The safety conversation always comes with it, and Gina was thoughtful here. She has been to places in the Middle East where she felt safer than she does in her own backyard. The fear we carry about other places is often disproportionate to what living there actually feels like. For instance, I lived in Khartoum from 2005 to 2009, during the Darfur war, and my day-to-day in the city looked nothing like what people imagined when they heard “Sudan.” This isn’t to say throw caution out; it’s to say that the news shows you a single story. Talking with recent visitors and locals, and your common sense will tell you more.

What changes when you put the phone down?

Gina described a post she’d seen in a travel group from a woman who had stayed in hostels for years and used to make friends easily there. She’d just done another trip to Europe and the experience was completely different. Everyone was on their phones in the lobby. No one was catching anyone’s eye.

I told Gina about a flight I took to Strasbourg a couple of years ago. I sat next to a woman, and we talked over the guy in the middle seat for the entire flight. Then we ended up meeting for dinner after we landed. My new friend knew a local restaurant, and when we got there she was comfortable enough to ask a couple at a nearby table if we could sit with them. We did. One of them turned out to be a rocket scientist. None of that happens if I’m scrolling on the plane and at dinner. The trip with the open eye and the trip heads down looking at your phone are not the same trip.

The phone is also a kind of social cue. Once one person picks theirs up, everyone else feels licensed to and it’s a downhill spiral. The space for an encounter to happen requires putting the phone down.

How small can the first move be?

I asked Gina what she would tell a woman who’s listening and thinking about her first solo trip. The answer wasn’t Lisbon, and it wasn’t a retreat in Bali. It was: take yourself out for lunch by yourself without your phone. No phone. See what happens.

That’s the actual invitation she leaves people with. The point isn’t the lunch. The point is the muscle. Sitting alone with yourself in public, paying attention to your surroundings, being available to a conversation if one happens but not depending on it. Once you can do that for an hour or two at a cafe near your house, you’re closer to feeling confident for your first solo trip..

You can hear a related thread in how to relax into solo travel after 40 and in what really makes a solo trip worth it. You can start easy, with one small choice you can make on a random Tuesday.

Join me in Skool

If something here landed, the simplest place to keep going is the Skool community. It’s where we work through the actual decision, not just talk about it. Bring the trip you’re considering, the lunch you haven’t taken yourself out for yet, or the question you don’t know who to ask.

Join the Skool community


About Gina: You can find Gina at Wanderlust Solo Women Tours, grab her free guide to Fearless Solo Travel, and listen to her own podcast Wanderlust Solo Women Travel “Unscripted” on YouTube. She interviewed me previously and that episode will come out soon. Gina’s also on Instagram at @wanderlust_momentum and @wanderlust_travel_coach, on LinkedIn, and on Facebook.

About Damianne: Damianne is the host of Freedom Looks Like This. Find more of her work at Damianne Coaching, grab her free starter gift for three steps to feel like yourself again (with one step being a solo activity), and follow her on Instagram and TikTok.

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