I love travelling. I think that’s most of us right? Especially now that we have #wanderlust images all over our insta feeds, encouraging us to dream of escaping the quotidian. Before this past December, it had been a while since I actually explored somewhere outside of my imagination. But my college bestie was getting married in South Africa, and I seized the opportunity to fly away. When I thought about it, I couldn’t actually remember the last time I went on a vacation! (I still can’t, so it’d been at least a few years.) Getting to South Africa from The Bahamas was going to be a trek, so I decided to build a 5 week holiday around the wedding.
I knew I’d need to connect somewhere in between the two countries. The most reasonable route went through London Heathrow, so I used this as a pivot point. In April, I bought a roundtrip ticket between Nassau and London, and as the year went on I figured out how to fill the time in between. When all the planning was said and done, I had a week in Italy, two weeks in South Africa, a little over a week in Wales, and my last few days in London-ish (outside Heathrow airport). Those 5 weeks were phenomenal.
I’m not using that word lightly either. When I reflect on my experiences, the ways I grew and the quality of my rest, I feel blessed to have taken this journey. And I’m proud of myself for making it happen! You’re probably wondering a lot of things, like how I could afford to take such a long holiday and how I spent my days. Well, I’ll be writing posts about these details, so keep your eyes peeled! I’ll share how I created a budget for my trip; how I saved and how much money I spent; how I determined what to pack – I crossed hemispheres and jumped between winter and summer :o; all the delicious things that I ate; and everything I did for fun. Stay tuned for those posts, but in the rest of this one I’ll say more about the journey as a whole and the things it taught me.

1. If you don’t plan it, it won’t happen.
It’s one thing to know that I enjoy travelling and quite another to make a trip happen. Once my friend’s wedding came around I realised that part of the reason I hadn’t gone away in so long was that I was waiting for an opportunity to present itself, when really I had to create the opportunity. There was a little struggle initially as I asked myself whether this was the right time to go on an adventure: maybe I should wait for something more epic or organic. Looking back that seems a bit silly, I mean, what’s more organic than piggy backing on a destination wedding?
My point is, through this process I realised that I decide what happens, and when. I’m single, childless, and even so it’s easy to forget that I’m in charge! Me! So I need to look up from my routine every now and again and make sure my life reflects my values.
2. Give yourself time to plan, because it takes time!
In the first place you need to be intentional about travelling. The decision making only starts there though, because you’re going to need to figure out all the details. This adventure took a lot of research, organisation and coordination. I did not buy my plane ticket in April and forget about the trip until departure day in November. No way! I spent an increasing amount of time as the year went on planning where I’d be going, where I’d be staying, what I’d be doing and how much it was likely going to cost me. Most of it was tedious – there was a lot to think about and tons of information to shift through! – but checking off little To Do boxes throughout the year felt good. Ultimately, the effort was well worth it when departure day came.
3. No matter the kind of work you do, rest is important.
This point is related to the first part of the lesson above. Another reason I failed to have a vacation in the last few years is I didn’t feel like I could take one. I didn’t even really feel that I needed one! As a freelancer, still figuring things out, I struggle with feeling like I need to keep working until I reach a certain level of stability – financial and otherwise. Beyond making time to read before bed and going to the beach in the summer, I never thought about taking a longer amount of time to rest. It wasn’t until I was on my holiday that I realised it was something I needed, not just wanted, to do.
There’s a reason companies give employees two weeks (or more) vacation; I’m committed now to regularly giving myself time off. Just because I’m responsible for my own work doesn’t mean I don’t also deserve it.

4.If you’re gone long enough, life will catch up with you.
When people hear I was gone 5 weeks I know they’re imagining that I was kicked back the whole time, eating and sightseeing and having all the vacation feels. If you’re one of those people I’m here to tell ya – go away long enough and life will catch up with you! By the time I got to Wales I had tons of laundry to do and even errands to run. There were also difficult things happening at home that I needed to be present for and help with. It didn’t matter that I was thousands of miles away, trying to keep the holiday as close to perfect as possible. Life kept trucking around me and I had to show up and participate.
This isn’t to say that you shouldn’t go away for extended periods. I would definitely go on a trip that long – or even longer – again. It just means that you need to adjust your expectations for what your holiday will feel like, what you’ll be doing, and the kinds of things that might pop up along the way.
5. The hard times are just as valuable as the good ones.
Part of my preparation for the trip involved acknowledging that there were likely going to be some uncomfortable times. I figured I might feel a little lonely at some points, and awkward at wedding activities since I only knew the people who would be the centre of attention. I didn’t think I’d have much by way of physical discomfort, but I packed a first aid kit and an umbrella anyway – and needed them both way more than I anticipated.
I wrote a post on instagram about my first day in Italy, the first stop on my journey. It was cold, grey and rainy (first time I pulled out my umbrella!). After spending a day to get to Catania I still had to find the right bus for the final leg of my journey, where I’d meet my host. That was a challenge since the signs didn’t make sense to me and no one really spoke English. Furthermore, there were no shelters, so I stood waiting over an hour, cold and tired, feet soaking in the drizzle, bags getting muddy. Things didn’t get much better that night and I went to bed wondering what on earth I had gotten myself into.
That was one of the low points of my trip, and it was the very beginning! A creep in Italy tried to pick me up, as though I were a prostitute. I used all of the painkillers in my first aid kit after two bouts of illness. I got bitten by fleas, leading to sleepless nights, paranoia about going to sleep, and taking still more medication from my first aid kit. I sprained my ankle and essentially couldn’t walk the entire time I was in England, which confined me to my hotel. Then, as I mentioned, there were the difficulties with my family.
In spite of everything, I don’t feel as though any of these obstacles ruined my trip. On the contrary, they were probably the things that most helped me see how capable I am and how much a positive attitude affects your experiences. I didn’t just learn things about the countries I visited; I learned things about myself and was pushed to be more independent and self-confident, since I was forced to navigate these situations alone. Moreover, I wouldn’t trade these difficulties for any others that might have arisen – worse sickness, theft, accidents.

When I look back on my adventure I don’t blot these challenges from my memory. It’s not like all the good things happened over on one side, with bad things over here but-let’s-not-talk-about-them-because-otherwise-things-were-perfect. I take everything together, one whole that I’m thankful to have grown from and experienced.
I hope my attitude encourages you to feel the same way when you face challenges on your travels. I hope that these lessons are helpful for you too, as you think about taking a big trip or are preparing for one right now! Doubtless you can relate to some of the lessons I’ve written here, but maybe you feel I’ve left things out. Do you have any travel-related lessons? I’d love to hear them in the comments below!
🙌🏾Awesome post! A lot of highs and lows but sounded like a great trip and thanks for sharing the lessons.
Thanks Travis! Glad you enjoyed it. 😀
Great post! Women can and should travel to the places they want to see. I traveled to Italy with my sister at the beginning of May but I had planned on going own until she said she wanted to go too. Keep seeing the world.
Sally
Thanks Sally! That sounds like a great trip with your sister. I intend to keep it up and seems like you do too. 🙂