You can begin traveling on your own now, starting slow, building up skills, and testing your confidence level. Learning is in itself a journey with some pretty significant benefits.
When you talk with friends who love to travel, they can usually tell you how they got started, especially if you buy the wine. My first trip abroad, in high school, was with a mixed group of students and recent retirees, a trip of a lifetime for all of us. For months, I slept with the brochure at my bedside, memorized the itinerary, and dreamed about what we’d see. It was a supportive first trip for a kid from the rural south to learn about currency exchange, public transportation, and why the English put butter on my ham sandwich. How do you make the next step?
Here are some great ways to begin. I’ve overthought this so you’ll see upcoming blogs on each possibility.
Visit a resort with lots of activities. This is how I began travelling alone, with a destination spa resort full of classes and events to schedule. I visited Miraval, a destination spa in Tucson, that was like summer camp for grownups. At the resort, I met people in classes, went to happy hour, and even had a seat at a single traveler’s dinner table. I was in control of the amount of solitude and independence I wanted. I met great people, but it was my trip.

Travel to a city that you would love to explore and find a ‘home base’ hotel. This is a wonderful next step. I chose Paris. I’d always wanted the time to walk the city and understand the two banks, the Ile de la Cite, and arrondissements. Picking the right hotel and making a couple of key activity reservations can make all the difference.
Then the big league. This may be where you start! For me, it took a minute. Letting go of home base, where the staff was there to help, and being truly on the road was a big step. Eventually, I tried riding the rails, then driving, and ferry-hopping. Once I was comfortable, I began to crave this freedom of the open road and the possibilities in a day all your own.
On that first trip to Miraval, I pored over the daily offerings and (yes, really) I made a spreadsheet to make sure that I could, if I wanted, fit everything in. This was very easy travel BUT it helped me learn to to think deeply every day about what I wanted to do (not what I should do or what I said I’d do, and not the spreadsheet). It actually takes a little practice.
What I Learned
- The Magic Moment. Feel that moment when you step off a plane, alone, in a new place, with only yourself. No expectations to fulfill, no one waiting for you. You don’t bring all your roles and identities with you unless you choose to. Blank slate!
- Self-management. One of the hardest things about traveling alone for me is not whether I know how to navigate the world but knowing how to manage myself. How do you respond when something doesn’t go well? How do you come back from that? Do you remember how to connect with new people? Do you want to? What do YOU want to do today? If you get a handle on this, you’ll see benefits in other areas of your life.
- Vulnerability. In other areas of life, you may not be great at asking for help. I practice this more when I’m traveling on my own. If you are gracious and a good listener, asking can make a difference. If I have a concern about my room, I engage the front desk in possibilities. If I need advice about the day, I ask. Your experience is precious. Admit you’re in new territory and sometimes the result is more than you imagine.
