The Best of How I Travel: To Plan or Not to Plan

The Best of How I Travel: To Plan or Not to Plan

After conducting 20 interviews with actors, athletes, musicians, writers and various other fascinating vagabonds, the most obvious conclusion to draw is that no two people travel alike. Everyone that we’ve talked with approaches life on the road from a unique angle, shaped by their own tastes and preferences. One issue that many of our interviewees have strong opinions on is the notion of planning ahead. Though everyone seems to agree that improvising is part of the travel experience, they differ on the how much to plan and when to simply go with the flow. This week we compiled some of our favorite answers to the question “Do you like to have an itinerary and some research under your belt when you visit a foreign country?”—hopefully it provides interesting food for thought as you set off on your own journeys.

To read more interviews from the How I Travel Vault check out our archive page!

I’m too lazy to read guidebooks or do research before a trip.

I’m not interested in the standard tourist stops and while I’m sure there is good information about places to stay and eat, I’d rather walk around and choose the place that looks best. As long as I have one contact to get me through the first night, I like to let the plan take shape on its own. (Holly Beck)


I think it’s smart to have a schedule and a plan.

However, I like to really keep my mind open. I often find myself doing things and going places that were definitely not on the agenda. Those adventures usually end up being the best ones. I was recently in Mexico and we hitched a ride in the back of a pickup truck to go check out a bird and alligator sanctuary. It was so beautiful and so majestic, but I never would have gone if I had stuck to the “plan”. (Hosea Rosenberg)

My travel style is defined by one thing: no itineraries.

I like to leave without even the seedlings of a plan. My tactic is to follow my nose, ask questions and talk to locals and tourists alike. It’s a scary theory, because it means opening up to the possibility of missing something big. But that’s always going to happen anyway. Whenever I find myself at a waterfall or beach that’s totally off the grid it suddenly becomes much easier to forget about what I might be missing. (Steve Bramucci)

I’m an Aries, and can happily veer from the plans.

However, my husband is a Capricorn, who needs everything settled before he hits the road. He’s the guy with the little string on the map, figuring out how far we can go in a day, and planning where to stay. (Ellen Hopkins)


I’ve been lucky enough to acquire a loosely-knit group of friends that travel a lot so before I travel, I usually ask around “Who do we know in Barcelona?”

More often than not someone’s been there or has a friend living there. Every city I go to, there’s someone I should meet, or go to dinner with, or ask for advice. (Coleman Collins)

Improvisation is the only way to travel.

If you make a plan ahead of time, you are going to miss out on the best experiences. Just wait and see what folks you meet along the way recommend, or follow some cute guy you meet traveling to another city. Whatever works as long as you get the best experiences you can. (Stephanie Izard)


I’m never going to see or do everything so it’s best to concentrate on what matters most to me.

Criteria? That which makes me grow. I figure I can suss a place out in about three days’ time. One, to walk around, two, to see some sights, three days to feel like I live there. (Don Wildman)

I’m not the kind of guy who can land and then say “where am I going to stay and how am I going to get there?”

I need to have lodging and transportation solidified before I set foot on the airplane. There are certain things that I can be spontaneous and flexible about, but I’m not a “hop from hostel to hostel” kind of guy. That being said, once I feel like I’ve arrived I feel free to explore. Whether that means going for a hike or visiting a museum or just sitting around by the ocean and doing nothing—I’m pretty flexible when it comes to the things I like to do once I’m settled…But I need to have a home-base. (Joey Harrington)


I’m blind when I go somewhere.

I’m going to Abu Dhabi in two weeks and I’m going blind. I think to myself, “So we’re going to the Emirates, Dubai is there, I know that, but I’m going to Abu Dhabi—I don’t know the difference yet: but I’m gonna see!” You learn things reading and in school, so you know a few things about most places—then when you get there you’re going to learn a lot more. You may not know about Paul Revere but when you go to Boston I can teach you about him. I was in Jamaica and I learned about Paul Bogle and saw where he lived. He was a revolutionary too. I’d heard of Bogle before and all off sudden I’m like “I see now.” I didn’t go there looking for it but “blam” there it is. (Leon Mobley)

I rarely research the places I go because I like to walk in with an open mind.

I usually only find out the currency exchange is, what plug adapter I need and the best way to and from the airport. (Johnny Jet)

I usually have a rough cut idea of a big trip a few months in advance but more often than not, I buy a ticket somewhere at the very last minute and just figure it out.

I always find the information in a place much more vivid and useful than pre-planning. (Kyle MacDonald)

If I plan things it’s never as good as when I just let my travels unfold, so flexibility is a must for me.

I trust the Great Spirit or Great Mystery to deliver me exactly where I need to be for what I need to learn or experience. (Sam Mehan)


I pretend to research a place before I go there.

I buy a novel and a work of nonfiction. I get a guidebook. It’s often quite painful to be standing outside of an airport thinking, “Huh, this is Bangladesh. Now where the hell am I going to stay and how am I going to get there.” I usually dig into the literature when I’m back from the trip. It’s much more interesting to read about places that you’ve been and histories that have happened to people you’ve met. (Kelsey Timmerman)

I barely give myself enough time to pack before a trip so research and planning are a challenge.

Wing it. You will find your way…or discover a new one. (Courtney Scott)

“How I Travel” is a BootsnAll series publishing every Tuesday in an effort to look at the unique and diverse travel habits of some of the world’s most well known and proficient road warriors. Got ideas for who we should talk to? Drop us a note.

You’ll find links to all the “How I Travel” articles on the How I Travel archive page, you can become a fan of “How I Travel” on Facebook, and you can follow the @howitravel profile on Twitter to get updates as soon as new features in this series are published.

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Older comments on The Best of How I Travel: To Plan or Not to Plan

22 June 2010

When I have a ton of time, I like to have the first night’s lodging planned and then wing it the rest of the trip. If I have a shorter trip planned, two weeks or less, I like to have more structure. But I have never had a trip planned out to the minute, and nor have I ever arrived blind into a country. I nearly did a few weeks ago in Turkey, and that was the subject of my last blog

22 June 2010

We have spent 986 nights during 9 trips in 25 years, in Europe, in our RV.

Our Travel method says..

If we can’t see IT this trip, we’ll see IT next time.

If we don’t care where we are, we aren’t lost.

If we have no itinerary, we’re just where we ought to be.

If we have no schedule, we aren’t late.

If we want to rough it, we don’t put ice in our Coke Cola.


Very interesting. I can not get on a trip without a basic plan. Nevertheless, it is interesting to go with the flow once you start. There are so many possibilities sometimes (but not allways, that´s why you should have a basic plan).