Why I practice Bookend Traveling & how overplanning can destroy the fundamental beauty of travel

Many people plan every moment of a trip, including each flight, hotel, train, restaurant, tourist attraction, and more. This theoretically ensures maximum efficiency and enjoyment within a trip, but I think it is a terrible way to travel and defeats the purpose of travel itself.

At least for me.

One of the most beautiful things about traveling to places I’ve never been is the act of discovering things I never knew existed. This experience, by its very nature, cannot be planned for.

This can take a variety of forms, from meeting interesting people and joining them for dinner, changing plans to explore a cliff I see in the distance, booking a flight or ferry to a nearby island, or simply taking moments of stillness in an empty monastery.

Early in my travel career, I adopted what I call “Bookend Travel Planning.” This means I plan the beginning and the end of the trip (the bookends), and some select experiences in the middle, but that’s about it.

Bookend Traveling = [Defined Beginning + Unknown Middle + Defined End*]

*Sometimes even the “Defined End” becomes undefined as well 🙃

1. Pick a section of the bookstore

There are so many different ways to travel, and I first need to do some broad stroke planning like, what is the first destination, is this in a foreign country, is this backpacking, kiteboarding, or a van trip? I’ll use a van trip through the East Coast of Canada as an example.

2. Choose the bookends

Normally there is something that forces this, whether it be flights, a set vacation, or another event that requires attendance. My bookends in my East Coast trip were pretty simple, I started with a mountain bike trip near Quebec City in September and needed to leave the Maritimes before it got too cold (ie: late October) since I had no heater in my van.

3. Cherry-pick some books

I mapped a general route, from Quebec City, through the Gaspé, New Brunswick, Magdalene Islands, and Cape Breton. But that was about it.

4 Let the rest write itself

Traveling light with a backpack, or in a van, lends itself very well to this approach as I can quickly change plans without too much overhead. This trip was incredible as I discovered many unexpected beautiful things along the way, including:

• 🕯️Lighthouse hopping and camping on Prince Edward Island
• 🏄🏼‍♂️Running into some old friends and surfing for a few days in Nova Scotia
• 🍻Chatting with a local at a pub in Nova Scotia led me to completely change my plans and end up on an 8 hour ferry to Newfoundland later that night

I should note, that the stories written are not always good, and things do go wrong, but this just adds to the adventure.

While some might call this lack of planning lazy, and maybe it is a form of procrastination, it has served me well over the years and I don’t intend to stop. There is a lot of unknown world out there to explore!