What I Wish I Knew Before My First Solo Trip

Last week, I shared with you my “Solo Travel Guide,” five challenges or activities to help ease you into solo travel.

In the coming weeks, I’ll be sharing stories from inspiring women about their first experiences with solo travel, along with advice and insights from experienced solo travelers.

To kick that off, I reached out to five incredible women and asked them what they wish they knew before their first solo travel adventure.

Here’s what they had to say:

Neha is a passionate part-time traveler and blogger based in India. Her special interest is helping people live happier, healthier lives.

Neha - Her Bags Were Packed - Solo Travel

I wish I had known just how liberating the experience would be. I waited for a long time before attempting my first solo trip because I was full of doubts. Eventually when I did take the plunge, I ended up kicking myself for not having done it earlier. Sure, there were stressful moments because I was travelling alone for the first time, and, of course, there were days when I felt pangs of loneliness. But the friends I made in the hostels, the amazing experiences I had on my trip, the sense of empowerment and confidence I developed, all of this more than made up. My advice to anyone reading this and wondering if they are capable of travelling solo would be – give it a shot! You’ll never know what you might find out about yourself.

Jeannie is an incredible artist based in Orlando, Florida. She specializes in photography and painting and travels for fun when she has the time.

Jeannie - her bags were packed - solo travel

I wish I had known how much I would enjoy my own company. I’ve always enjoyed being by myself, but you get to know yourself in a completely fresh way when you’re wandering a new city, turning down streets wherever you choose, dining wherever you wish, pausing for however long it takes to take a photo or jot down a sketch, etc. I also wish I had known how much I would be inspired, challenged and addicted to seeing/experiencing a new place for the first time, especially solo.

Kae Lani is not only one of my favorite people but is also a Philadelphia-based social media and editorial producer for USA Today’s 10Best. 

Kae Lani - Her Bags Were Packed - Solo Travel

When I started traveling by myself, I kept falling in love with everywhere I went to the point where I wanted to move there. I would walk around new cities, and, instead of just enjoying the trip, I'd literally start making plans to uproot my life in Philadelphia and transport it elsewhere. It sounds dreamy and cute, but inside the brain of a person who tends to set her sights on a goal and dedicates everything she has in order to make it happen, it can be quite a tumultuous mindset, and it ended up making me very anxious. It made life pretty unstable and it prevented me from really enjoying my actual home because I was so focused on trying to leave.

If I could go back and give old me some solo travel advice, it would be to stop planning for permanence and be here now. Nothing is permanent, and that's the point of travel. If you enjoy a place enough, you can always visit anytime! Places don't go anywhere -- you do.

Adrienne is a fellow travel blogger based in Washington D.C. Her first overseas trip was a disaster, but still she managed to fall in love with travel and now shares her adventures to help others prepare for their own travel.

Adrienne - her bags were packed - solo travel

I wish I had known that I didn’t have to travel alone until I was ready for it! Because I didn’t have a travel buddy, I thought that if I wanted to see the world, I had to strike out on my own. I lucked into finding small group tours on my second solo excursion. Looking back, I realize I used it as a kind of “training wheels“ for the travel I do now.

Small group tours gave me the chance to focus on the experience, without having to worry about how to get there. I learned to navigate public transit and got to stay in more off-the-grid spots. Plus, I connected with like-minded people who shared their own travel experiences. Small group tours gave me the confidence and knowledge I needed to travel solo.

Even now as a seasoned traveler, I still love group tours. They have enabled me to see places that would have been difficult to navigate on my own - like Morocco, for example.

Jen is a passionate and incredibly talented photographer with a special interest in photographing nature.

Jen Dobson - Her Bags Were Packed - Solo Travel

Her new website, Renegade Camera, is dedicated to curating a life of freedom and photography while helping aspiring photographers break in to the field by sharing her own journey and experiences.

I wish I had known how much fun I would end up having, because my first solo trip gave me some major anxiety. I had spent years saving up credit card miles and finally had enough to get me to Hawaii. I knew that I had no reason to be nervous, and that everything would be okay, but the uncertainty and unfamiliarity of it all was a little hard to overcome. Of course, everything turned out fine, and I had an amazing time. If I had known I was leaving for a trip that would include making new friends, riding in a doors off helicopter over the mountains, renting a shelter dog for a day of hiking, and riding a boat along the Na Pali coast with a pod of dolphins, I could have spent more time being excited. I want to make it a point now to go on solo trips at least once a year. The fear still finds me, but overcoming that fear is part of the growing experience that makes solo travel so special.


Interested in giving solo travel a try? Check out my Solo Travel Guide or Solo Travel Support Services.