The RTW Planning Balancing Act

With my role as the itinerary planner, I am struggling with how far out to plan and book things for our RTW trip. Being a planner and, yes, a bit “Type A” by nature, I am finding it challenging to let go and be more loose with this trip as much as I would like. Multiple times, friends and travel buddies of ours have encouraged us to not overly plan because that’s often when the best moments happen.

This was all great in theory when just chatting it up about our plans. But now when I am sitting here contemplating where to stay, how long to stay, and what to do in our first destination (Sydney, Australia), I am second guessing a lot of thoughts.

  • I say things to myself like, “Wouldn’t it be fun to just show up and not have accommodations or think about how many days to book yet?”
  • This is followed by, “Ok, don’t go crazy Rachel, book a few days accommodation, then go from there.”
  • And then, “Should we book further out? What if we miss out on this great AirBnB that I found?!”
  • Plus, “But what about snorkeling the Great Barrier Reef? Does that book up quickly? Should I book now or later?”
UGH!!! What to do?!!

I recently replied to Sam with SOS Travel ( on Twitter @Sostraveluk after she posted about facing her fears and doing a ziplining adventure. My message to her was that I have often found when I do things that put me out of my comfort zone I often have a blast and would have regretted it if I had not made myself do it. It got me thinking…will not planning so much along this trip take me out of my comfort zone and basically do the same thing? Practice what you preach, Rachel!

I do think part of it is just trying to keep myself busy so I don’t go insane while waiting to leave. Another part of it is the difference in planning for short- and long-term travel. For past trips, which were more like 7-10 days versus a year, we usually had flights, accommodations, tours, etc. pretty much planned out. Now with our RTW trip, there is so much more time to spare and flexibility around those “must do” things.

It’s hard not to go ahead and pre-book that awesome AirBnB at the base of the volcano in Vanuatu because it looks so cool and I don’t want to miss out on it. Then I tell myself that there are 15 other places to stay that would be great as well, and who cares if we don’t stay at that particular place! Plus, what if our plans change and we don’t end up in Vanuatu on those dates? We’re locked in!

Why not ask people for advice that have experience with RTW travel? That’s exactly what we did. 

Tim and Fin of Tripped ( have been great resources and so polite in answering all of our continuous questions. Their suggestions basically boiled down to this: book the first 3 or so days in Sydney, look at upcoming things like the snorkeling trip to the Great Barrier Reef that definitely need to be pre-booked, then work around the dates of those things you have booked and be flexible and spur of the moment with the rest. 

They also shared that their biggest regret in terms of pre-planning were the times they “boxed themselves into a corner” and wished they could have done things differently but already had things put in place. That is EXACTLY what I don’t want to happen on this trip. I would rather spend a few extra bucks, miss out on the accommodation we were hoping for, or have to spend more or less time in an area to work around things.

A great example of how keeping it loose and going with the flow is the recent post from Chris with The Global Stroll (, who just left on his own RTW adventure. He had an initial plan of what he was going to do when he reached his first destination (New Zealand), but within 3 days this plan had completely changed based on what he saw and suggestions made by others he encountered. 

Thank you, fellow travelers!

So I took Tim and Fin’s advice. I booked our first 3 days in Sydney and our snorkel trip, but other than that we are completely open. And you know what, it feels good.

I wonder when the first time is going to be along our trip that I actually get annoyed at the fact that we have to show proof of onward travel, schedule multiple things ahead of time, or something else messes with my new found chillness and unstructured ways?

What are your thoughts? Any suggestions on how to plan…but not over plan?


A&L · April 29, 2018 at 1:11 am

We book an airticket to where we want to go and the first night’s accommodation, and research what local SIM will give us good coverage at a good price for wherever we think we might go (data necessary, calling optional – we can stay in touch with each other and home on WhatsApp or other apps) After that it’s the Dwight Eisenhower quote “I have always found that plans are useless but planning is indispensible”

    Peter & Rachel · April 29, 2018 at 8:52 am

    Pre-researching local SIM cards is a great idea! We hadn’t thought of that!

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