A few weeks after I booked my one-way ticket to Bangkok, one of my besties called to tell me her and her husband would also be headed to Southeast Asia in April- Her husband had a business retreat to attend in Singapore.

When they invited me to join them for a few days, I was reluctant. The whole purpose of my travels was to get out of my comfort zone. To meet people and go places I didn’t even know existed yet. I feared making plans would disrupt the organic nature of long term travel.

However, her invitation also made realize how lucky I am to have friends who like to travel. Pushing 29 years old, I have come to learn how rare it is to maintain childhood friendships into adulthood, (and actually still have something in common). With that in mind, I couldn’t pass up the opportunity to explore the other side of the world with my life long friend!

Singapore hadn’t even been on my radar, but it didn’t take me long to get excited about it! Before I left the states we researched activities, pre-booked flights and accommodations and even arranged for my friend to come back to Thailand with me after Singapore. While making these plans I had no idea what a lesson they would teach me about pre-booking.

Not Pre- Booking Didn’t Cross My Mind

When I first started traveling in my early twenties, not pre-booking a trip didn’t even cross my mind. Every trip I took had a solid agenda. I pre-booked nearly everything, from transportation to accommodations to excursions. Doing so gave me peace of mind. I could rest easy knowing everything would be taken care of when I got to my destination. But, I must admit, I often felt restricted upon arrival. I didn’t have the flexibility to change destinations on a whim or extend my stay in city I fell in love with. The few times I did decide to stay somewhere longer, I had to reschedule flights, and man, it cost me!

During those early travels, I met countless backpackers, and read even more blogs, about people who didn’t book anything prior to their arrival- not even their accommodations. After seeing how easy they made it look and the flexibility it brought, I intended to apply their methods to my own long term trip

But then I booked Singapore…

And about a week before I left home, I booked a guesthouse for my first two nights in Bangkok…

I simply couldn’t not plan!

From Binge Vacations to Long-Term Travel

You have to understand, I wasn’t introduced to backpacking culture or long term travel until my twenties. The traveling I did as a kid consisted of a yearly trip to Wisconsin, a trip to Disneyland and a Caribbean cruise. These trips were planned out months in advance, they were never longer than a week and my mom spent the rest of the year recovering financially.

I have a lot of fond memories from those trips but what I remember most is the stress of squeezing a ton of activities into a shot period of time and spending more than we could afford. Because of these binge vacations, it was easy for me to see the value in slowing down and spending within my means when I started to travel as adult.

The need to plan and pre-book, however, was more difficult to shake.

I Pre-Book Out of Fear

I do it to eliminate the unpredictably- but why? Long term travel is an adventure and an adventure, by nature, is unpredictable. Why am I am fighting the very thing I desire?

I don’t want to take a quick, overpriced, binge vacation, like I did as a child.

I don’t want to know exactly what is going to happen and when.

I don’t want to overextend myself by trying to fit in every excursion, monument, temple and activity available.

I want freedom.

I want to explore.

I want to connect with new people.

I want to allow these opportunities to lead me to new experiences.

I want these new experiences to change me and force me to grow.


Noting catastrophic will happen if I don’t have a room pre-booked for the night of my arrival or an excursion planned for every day of my trip. Actually, these are the very things that will prevent me getting everything I want out of this trip.

Fewer plans equate to more freedom, more exploring, more human connections, more new experiences, more personal growth, more change and more ADVENTURE.

Thank You Singapore!

Point blank, my trip to Singapore solidified that pre-booking does not align with my long term travel goals.

When it came time for me to head to Singapore, I wasn’t ready to say bye to Bangkok. I’d met some cool people and probably would have stayed a few more days, or carried on traveling with them, had I not already had a flight booked and people expecting me on the other side.

Singapore was by no means a disappointment though. I had a great time with great people and learned a lesson I needed to learn- to resist pre-booking! For the foreseeable future, I am not going to pre-book anything before I absolutely have to. If I happen to cross paths with people from home or decide at the last minute I want to meet up with someone somewhere, great! If not, it wasn’t meant to be. I want to see where this trip can take me organically, without anticipating everything before it happens!

Thank you Singapore!

Let ADVENTURE continue!…