Koh Kood Thailand Sunset

Why I (Almost) Never Book in Advance

This article was written with inspiration from the Reach To Teach: Teach Abroad Blog Carnival, a monthly series that focuses on providing helpful tips and advice to ESL teachers around the globe. This month’s host is Maggie Attoe. Check back for more articles, and if you’d like to contribute to next month’s Blog Carnival, please contact Dean at dean@reachtoteachrecruiting.com, and he will let you know how you can start participating!

This month’s blog carnival question: What advice would you give people getting ready for their own adventure?

Why I (Almost) Never Book in Advance

Travel, in the more generalized sense of the word, is unpredictable. It’s flawed. It’s risky. It’s full of people and places and cultures, which means that even the most prepared traveler can’t plan for everything. And that’s the beauty in it.

Even a cruise boat traveler who likes to know where they’re going to sleep and eat each night (ahem, my parents) can’t predict the outcome of every situation. Something could always go wrong with the ship, perhaps a stop is canceled due to security issues on land, or maybe the tour itinerary didn’t go exactly like the pamphlet said.

It’s how we handle these issues that tests our inner traveler.


In Thailand, I was swapping travel stories with a friend I hadn’t seen in a while, and she said this to me: “We’ve been gone over six months now and haven’t had anything like that happen to us,” referring to her boyfriend and herself after I told them about the four-foot cobra I nearly stepped on in my beach bungalow bathroom.

It might sound strange that anyone would want to wake up to a cobra in her bathroom, but if you’re a traveler, you’re also a storyteller (written or verbal), and even if you don’t initially understand that these unexpected experiences make great stories, you will. And the best part of storytelling is getting to live those special unexpected moments all over again.

“Do you always book things in advance?” I asked my friend.

“Yes,” she admitted. “I like structure.”

I know she’s not alone. Many people want to have a plan, however loose, and show up with a place and an address ready to show the taxi driver. There’s absolutely nothing wrong with that…unless you also seek spontaneous interaction. It’s difficult to have both.

If I were in the habit of booking ahead, I wouldn’t have wound up spending the night with a village family outside of Hue, Vietnam. I had a rented motorbike and no place to be, so when a nice man invited me back to his home (for coffee, not to stay), I hesitantly accepted. I trusted my gut when it said he was harmless, and it developed into a very memorable experience.

If I had booked in advance, I might never have found the homestay down a rutted and muddy road in Khong Lor Village, Laos – it isn’t online, and there are no signs, even at the wooden and stilted residence of the local Laotian family of five.

If I had listened to the many people who said I must book early if I wanted a place to stay at the Maha Kumbh Mela in Allahabad, India, I wouldn’t have woken up on the floor inside the thatch hut of an orange-robed, dread-locked sadhu four mornings in a row, and pinched myself in disbelief that I managed to immerse myself in the world’s largest religious gathering along the holy River Ganges.

kumbh mela sunrise sillouhette

The bathing ritual at the Kumbh Mela in India

Because I don’t corner myself into a money-losing position, I’ve afforded myself many life-changing experiences. And if I weren’t fortunate enough to meet the people I did, I would have simply had to find a hotel room somewhere nearby, which puts me right back to the same position I was in before – with nothing lost. And no unique experiences gained.

I admit this isn’t always smart. There are situations that will require a bit more planning, but my advice is to be careful of paying for something you’re going to feel obligated to use. If you’re like my friend and you crave structure, my advice is this: look online to find a hotel in an area that sounds good, like you would normally do, but don’t book it. This way, you’ll have an address to give the driver, and the freedom to change your mind.

Keep in mind that every failed attempt, every pothole, every steep climb is a potential story. You’ll look back on your travels with fond memories of even the things gone wrong, and you’ll tell them with a smile, a lightness in your voice that says, “I did that. I learned from it, and I’m a better person because of it.” So don’t take yourself, or your plans, too seriously. Just embrace the flow, and ride the wave.

Why I (Almost) Never Book in Advance
Written by:Jessica J. Hill


  1. Marilyn Jones says:

    To plan or not plan? Either way, to travel is to live!!!

  2. Very good advice. Traveling with kids makes this a bit harder (a lot harder), but it is always the unexpected happenings that make for the best stories!

  3. Dean Barnes says:

    Spontaneity is golden for travel!
    Me and my partner call ourselves whimsical travelers (i’m not even sure if this is a term) but basically we have been known to decide on the day or the day before to just up and go somewhere and see what happens. I have found that this opens up a door of wonder and gives traveling a deeper level of adventure. It totally enriches the travel, instead of speeding on the scooter to reach the hotel on time, we’re stopping off and taking in the beauty of the scenes our travel has given us.
    Literally stopping to smell the roses!

    Great read, I look forward to reading more from your blog carnival posts.

    • jessicajhill says:

      I love that term – whimsical travelers! I love waking up without a plan and just heading off in a direction to see what you find. Some of my favorite experiences have happened because I took the journey slow enough to allow them to. Thanks for commenting!

  4. Rebe says:

    Great post, Jessica! I always book a hostel in advance, but it was fun to read your stories about when you didn’t.

    I’ve found that being a blogger makes it easier to find the silver lining in unfavorable situations — at least I have a story to write about! Sometimes when I find myself in uncomfortable or awkward situations, my mind just automatically pictures myself retelling it to a close friend, and I’ll laugh out loud at the absurdity before I’ve even gotten myself out of the situation! Makes it even more awkward / funny : )

    • jessicajhill says:

      You’re a true traveler turned storyteller, it sounds like! It’s so fun to retell the moments of terror or absurdity and be able to laugh at them later…or in the middle, in anticipation of laughing at them later! Thanks for commenting!

  5. Tracey says:

    Planning spoils the fun doesn’t It? Here’s to riding waves.

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