Itineraries – Homemade Prisons?

by Keith Savage · 1 comment


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As the first imaginings of a new trip percolate in my mind, I find myself drifting toward a familiar groove: obsessive over-planner. I have mastered the art of blending guidebook recommendations with internet investigations. No region can go unscouted, no accommodation unobserved. Nothing is safe from my prying eyes. A perfect, unblemished itinerary must emerge!

The fact is that I really enjoy travel planning and, like most seasoned travelers know, it’s a method of extending your trip without actually being there. Every leg of the trip, every city, every throat-catching vista can be envisioned again and again. And the excitement builds. After all, you’ve chosen your destinations with purpose, right? Let’s take for granted that you haven’t just plopped your finger down on a spinning globe. There will be some unforeseen circumstances; flights might be missed, hotels booked, cars not reserved, but generally the trip should be just as good as you expect.

But there’s the rub: expectations.

There is the distinct possibility that in the midst of your planning smorgasbord you have systematically eliminated any chance for pleasant surprise. For amazement. For finding your own path as you walk it. I usually feel this soft pain post-trip, though there have been a few times in my travels where pleasant surprise…uh..pleasantly surprised me.

Porto, 24-hour Love Affair

For instance, last summer my wife and I spent three weeks exploring Portugal as part of a sabbatical from work. Our goal was to soak in the culture and see as much of the country as we could. We rented a car and planned stops to mesh with desirable areas, though some cities were just places to rest our heads or act as bases for the region.

We allotted a single night to Oporto in our three week itinerary and for shame! Fie! Fie, meticulously-planned itinerary! I might have driven through tears as we proceeded toward Braga (also tear-worthy) the next morning, but I can’t recall (thanks Sandeman). It was like saying goodbye to Frodo at the Grey Havens. We knew we needed more time in Porto the moment we glimpsed the city from the winding river road.

The historic downtown of Porto straddles the mighty Douro river and has been demarcated as a world heritage site. Rightfully so. An air of the Renaissance followed us through the narrow streets and alleys and we walked beneath the rainbow-hued buildings. Umbrella-filled praças led to café-lined river banks. Far above the river, Eiffel’s bridge connects the downtown with the Port wine lodges on the other side of the river. The food was excellent northern Portuguese fare. The people were warm and immediate companions. When you go to Porto, you must must must stay at Guest House Douro, which stands along the river bank in the heart of the downtown. This can be your splurge if you’re on a budget. Tell Carmen and João we said hi.

Wayfaring Vampire Uses Google Maps

Porto enchanted us. I can’t help but think part of the power of that enchantment was due to my lower expectations. How many places have I skipped because we needed to be elsewhere? How much more enthralling could our days and weeks abroad have been if we’d winged it? Had I sucked all of the freedom and liberation out of the act of travel like some wayfaring vampire?

Surprise is one of the greatest joys of travel. Obsessive over-planning can be a real thorn in your side if you’re passively seeking surprise; over-planning can also reek of fear. Make sure that that isn’t underlying your itinerary-making motivations. Some places really do need to be planned out in detail, but most trips benefit from built-in flexibility and options for alternate routes. You never know where your path will take you when you don’t Google Map it ahead of time.

Have you ever planned a trip itinerary only to feel constrained by it on the road?


AkilaNo Gravatar December 30, 2009 at 3:27 PM

We have struggled with our need to plan trips, as well (in fact, I wrote a whole post about it here: https://www.theroadforks.com/offtheroad/why-we-plan-our-rtw). In Italy, we had prebooked all our hotel rooms because everyone told us how expensive and difficult it would be if we went there to find rooms, but when we got there, we realized that we didn’t want to spend as much time in Florence and wanted to spend more time in Tuscany. On the other hand, planning saves so much money and we have gotten to see some amazing things (like St. Peter’s tomb) because we planned. It’s a tough call to make and one that we are still struggling with as we continue to travel.

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