To plan, or land and go with the flow? That is the question.

One of the traditional hallmarks of vagabonding is the idea that you’d arrive in a new destination having done the minimum required when it comes to advance planning. Maybe you’ve got a place to sleep for the first night, maybe you know a few things in that city or country that you definitely want to see or do or eat – but in general, vagabonding has long been about experiencing life as it’s presented to you, and not having an agenda or list of things to check off.

Today’s vagabonder may still embrace that “come what may” attitude much of the time, but most RTW travelers these days have something of a plan worked out for their trips – where they’ll go, how they’ll get there, what they want to see and do along the way, etc. One BootsnAll member, however, is wondering whether his usual practice of planning things in great detail is going to be the best way to go for his upcoming RTW trip.

Wojtek presents the question on the BootsnAll travel message boards:

I’ve always been a person that plans things in detail, however if I don’t follow the plan I don’t feel out of my depth. But I’d like to know what I’m compromising/passing on as I change my plans.

I’d love to hear from people that just made it up as they went along and those that planned in detail. Should I put more effort in and put myself at ease or just book a one way ticket and go with what feels right at the time?

It sounds like Wojtek doesn’t mind changing plans along the way – as long as he knows what he’s missing, and is content with missing it. But what if you don’t know what you’re missing, and you still have a grand time? Does it really matter what you’ve missed?

Wojtek’s rough itinerary is sketched out in the message board post, and he’s looking for input on whether to work out a detailed plan or just stick with the rough plan and let the rest of the trip happen as it will. What’s your take? What did you do (or are you doing) for your RTW trip? Leave your tips in this thread on the BootsnAll boards.