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My first solo trip was two years in the making. Originally, it was supposed to be a long weekend in Montreal, but that got derailed by the pandemic when Canada closed its borders. Finally, this past summer I made up my mind to rebook my first solo trip to St. John in the US Virgin Islands instead.
I’d been to St. John many times before, and figured my familiarity with the island would help lessen my rampant pre-trip anxiety. I did the best I could to thoroughly plan this trip and avoid potential mishaps.
My lodging was in Coral Bay, which is where I normally stay with Aaron and his parents. My flight times were good and connected through the Philadelphia airport, another place I was familiar with.
Much as I tried to eliminate room for error, the universe had other plans. I’ve since made it home, and am sitting cozily in sweats while typing away at my laptop. However, I’ve decided to share all my mishaps below to help you avoid them, or even show you it’s okay to have an imperfect trip.
After all, you can’t have growth without putting yourself out there for mistakes, and things happen!
10 Challenges of My First Solo Trip
Here are the biggest issues and mistakes I encountered during my first solo trip, many of which brought on tears of frustration. While I did complete the full week, I’ll admit that a couple days in I was considering calling it quits and heading home early. True story – I was looking up flights and found some temptingly affordable options.
1. Unusual Window Seat Claustrophobia
I have selected window seats for myself so many times on planes. I especially love them when traveling to the Caribbean so I can easily see the turquoise water when we get close to the islands.
This past time was different though. After I took my seat, a mother and daughter sat next to me. Suddenly, I got this weird trapped feeling that I’d never once gotten before. Also, thanks to tight layovers, I didn’t get to have my pre-flight wine, which may have contributed to my stress.
As luck would have it, a window seat opened up next to the girl’s dad, and she moved there. With an empty seat now between me and her mom, I felt so much better. I learned that if I’m not traveling with Aaron or someone I know, perhaps I’d do better with an aisle seat.
2. Forgetting to Turn off the Emergency Brake
Before my first solo trip, I had never driven a Jeep on St. John before. The island is very hilly, and the use of an emergency brake is often necessary when parking. In contrast, I live in flat Ohio, where we typically don’t need to use an emergency brake.
Picking up my rental car was easy enough, and I pulled out of the driveway to begin my first drive across the island. I was quickly flagged down by a local walking down the sidewalk, who informed me that my emergency brake was on. I sheepishly moved to correct the issue, while pretending I understood what I was doing.
Thankfully, I did figure out which lever the emergency brake was. However, I would catch myself repeating this mistake over and over throughout the week. I think it was by day three or four that I finally stopped beginning most of my drives with the emergency brake on!
3. Arriving to a Full Trash Can
This was more of an annoyance than anything else, but I was super frustrated to see the kitchen trash can was full to the brim upon my arrival. I tried in vain to contact the property manager, but unfortunately after 24 hours no one had come to pick up the trash.
By that time, I was piling my trash on the counter, so I ended up begrudgingly taking it out myself. In St. John, that means putting the bag in the back of your car and driving it to a smelly dumpster down the road. The last thing I wanted was to experience the waft of a stranger’s trash while driving around the island.
4. Tricky Vacation Rental Driveway
While I found my vacation rental just fine, the tiny, narrow driveway was not quite what I was expecting. It was up a huge hill with a cliff to my left side, and you could really only pull into the driveway when going up the road because of the angle.
However, it was pulling out of the driveway that most intimidated me because it was blind, uphill, and at a sharp angle to the downhill road. I asked the man who guided me to the property for advice, and he said to back down the road and into a driveway across the street to turn around. You know – just your totally normal way of exiting a driveway.
The thought of backing out and down the road scared me, as the vegetation around the driveway made it impossible to truly check for traffic. I didn’t think I could do it, and even messed up my first attempt (described below). I collapsed into a puddle of tears that evening in deep self-pity.
However, not one to stay down, I woke up refreshed and ready to face the task at hand. I still didn’t know how I was going to do this, though. Lucky for me, there was a construction crew just a little down the road that morning, and I was able to get one of the guys to help guide me.
After this miracle, I was good to go for the rest of the trip and actually got pretty good at the driveway by the end of it.
5. Almost Needing Roadside Assistance Night One
Did I mention driving on St. John is harder than I initially thought? I’d watched my husband do it so many times, and never realized what a challenge it would be.
This was proven to me night one, which was the first time I tried to leave the driveway by backing down the road. As soon as I pulled out onto the road, I totally bailed on backing down and instead began driving further up the hill. This was the wrong direction, and I needed to find somewhere to turn around.
Unfortunately, I couldn’t find anything easy that wasn’t another scary, blind driveway. Then, to my horror, the road dead-ended. My only option was to back down a steep driveway to turn around, all while avoiding a sharp drop at the edge of the road.
As I assessed the situation, the thought of calling the Jeep company to come save me did cross my mind. However, I didn’t know if or when anyone would come, and whether I’d be charged for that.
So I steeled myself, backed a short ways down the driveway, and managed a K turn back down the hill. I cried tears of frustration that night, not knowing the breakthrough I’d have the next morning.
6. Super Loud People Staying Above Me
I was initially happy to be staying in the lower apartment of a villa, so that I’d have people staying above me. For safety reasons, I didn’t want to be totally isolated. However, this blew up in my face.
The people staying above me showed up the second night of my stay, and they proved to be a rowdy bunch. It sounded like they were slamming every door and drawer, and I heard the constant sound of them dragging patio chairs across the deck. They spoke so loud I could hear their conversations, and I could also tell the exact songs they were playing and singing along to.
It was so bad that I truly didn’t think I’d be able to stay there. I even tried to book a new Airbnb to use for the rest of the week. Unfortunately, the host cancelled my reservation citing that she didn’t have enough time to get it ready.
At that point, I was stuck because St. John was just about fully booked. Instead, I got in contact with the property owner, who spoke to them. Thankfully, the noise improved after that.
7. Almost Returning From My First Solo Trip Early
My noisy neighbors and driveway issues had me extremely frustrated. On top of this, I was dealing with loneliness and questioning whether solo travel was truly worth it. Despite being in such a beautiful place, I sat in my vacation rental – you guessed it – crying again and looking up flights home.
I spent the evening deliberating my next move with Aaron, who helped me decide not to cut my first solo trip short. To be honest, those were the words I was hoping to hear. He knew how important this was to me, and him believing I could stick it out was everything.
8. Moments of Loneliness
While I wasn’t always lonely during my first solo trip, there were some moments in particular when I really felt it. Unsurprisingly, it was worst when I was eating at a restaurant – especially if I couldn’t get a bar seat.
It made me sad to see couples seated around me. They brought to mind all the fond memories I have from mine and Aaron’s adventures together.
What helped me get through these times was reminding myself why I was doing what I was doing. I wanted more travel in my life, and had quit my accounting job to do so. Aaron is still limited by vacation time, so if I want to get out more, sometimes it’ll have to be alone.
I know other solo travelers have felt the same, and it’s totally normal. I also want to point out that there were also plenty of times when I felt totally fine and was enjoying myself!
9. Finding a Roach in the Apartment
After all the frustration I’d already had with this vacation rental, finding a roach was the third strike for me. On one of my last mornings, I encountered the biggest cockroach I’ve ever seen in the kitchen sink. I seriously considered leaving it there in the hopes that it would disappear.
Then something in me rallied, and I managed to attack the roach with bug spray, soap, and water. It worked, and I trapped the little nasty under the drain.
However, I was then too scared and grossed out to use the kitchen or even spend more time in the apartment. Therefore, I found a new place to stay for my last night and was so happy to move on from that apartment.
10. Going Over Budget on Eating Out
Until I got home, I was afraid to look at my credit card statement because I knew I was eating out more than planned. When my trip was done, I finally worked up the courage to update my budget vs. actual expenses. Sure enough, I had definitely gone way over on food.
I determined this was because I had eaten lunch out every day, even though I had originally planned to make sandwiches. This didn’t pan out because the grocery store was out of bread and lunch meat on day one. The next day, I day-tripped to Lovango Resort, where I was not allowed to bring in any outside food.
The day after that I realized I had no sandwich bags, and it was too much of a hassle to run out to get them before going to the beach that day. The day after that I took a boat trip that provided lunch.
Finally, the next day I saw the cockroach and didn’t even want to go near the kitchen. So yeah, I ended up wasting lunch food, which I am not proud of. I’ll do better next time!
Finally: Returning From My First Solo Trip
For funsies, I’m throwing in one last surprise I encountered during my trip home. My flight from St. Thomas to Philadelphia was fine and had no drama. There were no children behind me to kick my chair, and I had an aisle seat next to respectful people.
Rather, it was my hour flight from Philadelphia to Cleveland that proved interesting. Due to storms in the area, many flights were being rerouted, and shorter ones were told to fly at 8,000 feet. To be honest, I didn’t notice anything off while en route, but I’m a nervous flyer and was a bit unsettled at first.
Even my father-in-law, who has flown frequently all over the world, has never experienced this. That tells me it truly was unusual!
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The goal of this post is not to scare any female off from solo traveling. I simply seek to share my own experience and show you that things happen. This is true no matter how well you plan and no matter how beautifully crafted your itinerary is.
An imperfect trip does not make you a failure, or mean that you shouldn’t solo travel again. These hiccups definitely haven’t deterred me. In the moment they were stressful, but in the end they’ve helped me grow stronger and more confident.
