For me, what began as week-long explorations of single cities (which I highly recommend) or a low-risk itinerary hopping trains across a country I love has  evolved to adventures that add more and more challenge.

Pushing myself with a new challenge brings me home with more confidence and assurance in what I can do in everyday life. There is always learning – figuring out public transport, acclimating to the pace, and managing to buy a coffee in Italy. (It’s not easy.) By the end of the trip, you find the perfect view, buy the coffee, begin to feel at home in a new place and at home in your own skin.

New challenges are an important part of why I go solo. On recent trips, I’ve done  more driving and spent more time out in the natural landscape. So fewer museums, more mountain roads.  My lifelong commitment to a stick shift paid off.

This past year was a new step for me with solo travel.  As I passed a big birthday, I wanted to reclaim a hobby or skill from my past, something I could reclaim and keep.  So after almost a year of lessons, off I went to Mallorca for a week of horse riding.

If you are a school or a course junkie, you may have had thoughts about a cooking tour or language immersion or, like me, a school for equitation.  I learned a little more than I expected – I realized that what  makes this kind of travel work are the constant opportunities to start over!  Yes, the Do-Over.

When you are alone in Iceland and do something unbelievably stupid, you make it back to the hotel, (in my case dry off), get a good night’s sleep, and start over! While you are conquering the world, the presence of strangers allows you to make mistakes, step back, try again and hopefully take the day…eventually.

With a week-long class or clinic, you have an epic fail, get a good night sleep, get up and see the same people again at breakfast.  I am not a good rider.  I learned this in bold new ways on my trip. Most of the experience was spectacular…but part of it was like being back in high school gym class but with better and more expensive workout gear.

My best moments were when I slipped away in the tiny blue Fiat I rented and navigated the hill towns on the island, found hidden backroads, and learned how to pay a parking ticket (all of this as you can imagine is related).

Push, try new things, leave time for complete relaxation – but as you travel, you’ll become more aware of where you find your joy.  What’s next for me?  Driving across Ireland, this time with a friend!

What I Learned

• If you are looking at a learning trip, think about the pace. Is there time for your own adventures? Do you love meeting new people and cherish the group time? What do you want the experience to be like?
• If it’s learning a skill, give it up a little. It won’t be the same – the accents will differ, the horses won’t have the same gaits, the cooking measurements aren’t as familiar, the instructor has a different approach.  Be ready to shift.
• Start below your perceived skill. Take the pressure off. Who doesn’t want to be promoted once you are there?
• Most of all, appreciate the journey itself. I wouldn’t trade moment of my year of lessons preparing for the trip. It was the best part but it took planning a trip to get me started!