One note or two about planning the trip of a lifetime

If you think pulling together a complex trip is the kind of organizational nightmare that’ll make you feel like you’re in a bad remake of a Vacation movie — don’t worry. There’s an app for that.

Take it from me: I’ve been on the road with my family for the better part of a year, often for weeks at a time.

These aren’t the kinds of trips you can delegate to a travel agent. They’re multi-stop, cross-country adventures involving planes, trains, ferries and an occasional horse-drawn carriage.

Only one or two itineraries have included hotel stays. The rest of our accommodations have been unconventional, from checking into a seaside cottage in New England to a secluded rental cabin at the edge of a national forest in Wyoming, to, ahem, not sleeping at all while we drove through the night.

So where did I turn to plan an epic family road trip?

I didn’t want to learn a completely new system. Instead, I preferred to incorporate the applications I currently use into a solution, harnessing them them into a usable trip-planning tool.

I tested several productivity applications for my computing platforms — including my iPad and laptop –and was surprised to find the one that worked the best was hiding in plain view. It’s a little program called Microsoft OneNote, which is free on my iPad. (A more feature-rich version of OneNote also comes with the latest Office suite on a PC.)

How we use it

OneNote gathers all of your files into one place, where you can share them with other trip participants.

To plan our upcoming trip to Hawaii, we started by adding potential dates into our calendar. I rely on my cloud-based calendar, but Kari, my better half, prefers the calendar application on her computer.

We also keep a spreadsheet with destinations and contacts, including phone numbers, addresses and emails. Since Kari has an MBA she likes to put everything in a spreadsheet.

And then there’s another layer: the photos, snippets of information and hyperlinks to websites, all of which are collected in random Word documents. Plus, the multiple emails from sources and friends offering advice about where to go.

And don’t forget the maps. Not only do you need to know where you are and where you’re headed but you want to know how long it will take to get there. That’s a critical part of the travel planning process.

I already collect this information using various programs – the spreadsheets in Excel, the text in Word and the maps in Bing or Google maps.

The kids aren't worried about the itinerary.OneNote allowed me to organize my information in an intuitive way, creating pages for the information that resembled a digital scrapbook. Instead of forcing me to think like a computer, by organizing a trip around a series of documents, OneNote let me organize it by a topic or destination.

For example, our Oahu segment isn’t a folder filled with random files, but it is instead a “book” that looks a lot like an itinerary that a professional travel agent might give you before you embark on a tour or cruise. This was important as we visited four islands and had to change our plans a few times at the last minute.

If you’re on the obsessive-compulsive side, like we are, you can also create multiple checklists to follow your progress. That way, you know what still needs to get done, what’s already been done and where you can procrastinate.

OneNote had a few quirks. The iPad app only handles 500 documents and if you want more horsepower, you have to upgrade to a paid version for your PC. Also, changes made to one document won’t automatically populate to other shared documents, at least in the version I tested. But OneNote is one of those indispensable apps that have vastly improved our ability to plan a trip.

Strategies for travel planning

Most of all, OneNote helped us re-think what good trip planning means. Here are a few strategies we picked up along the way:

Don’t overplan. It’s possible to do too much research and plan for each moment. Leave some things to serendipity, otherwise your itinerary will get too cluttered and nothing about your trip will be spontaneous. And the spontaneity can be half the fun. After a few cross-country trips, we felt more comfortable winging it, and we made some great discoveries as a result. Like Deschutes National Forest, the dormant volcanic near Bend, Ore., which we didn’t know about until we decided to pull over for a picnic lunch.

Simple is better. No matter how complicated your itinerary, there are ways to streamline the process to include the important information and exclude the extraneous details that will be insignificant until you arrive at your destination. For example, we whittled a list of recommended restaurants down to a hyperlink that we could access later, instead of trying to save everything to a document.

Share your itinerary. Letting people know where you are is helpful when you’re on a multi-stop itinerary. When your hosts know where you’re coming from, where you’re supposed to be, and where you’re going, you can avoid all kinds of trouble. That’s why car rental companies ask for your flight itinerary – they aren’t really interested in which airline you’re using. They want to track your flight so that if your plane is late, they can hold your rental vehicle.

Pad your schedule. Remember the 15-minute rule: For every one hour on the road you should plan 15 out of the car. (And not necessarily every hour; we would drive three hours and pull over for half an hour or so, give or take.) You need to stretch, eat and take a break from sitting. Also, you can never plan too much time for meals and national parks. If someone recommends half a day in a national park or forest, take a whole day. You won’t regret it.

Be flexible. Life is too short (and so’s your trip) to lock yourself into a schedule. If you see an opportunity to do something interesting, to make an unexpected detour, or to extend your trip – do it! Just don’t forget to share your new itinerary with everyone along the way. Our favorite detour? The Grand Canyon, a day-long diversion on a road trip from California back to Florida. It was way off our designated route. And so worth it.

Our kids probably don’t realize the amount of work that goes into scheduling a year on the road, and maybe they think because their mother used to be an event planner, that it’s all pretty simple.

Please don’t tell them the truth – that it’s the technology that makes it all look easy.

Christopher Elliott

Christopher Elliott, a.k.a., Dad, is a writer who spends way too much time in front of a computer.


  • http://www.facebook.com/KarenellBrown Karen Brown

    Have you used Tripit? It scans my inbox and adds everything for me automatically and auto-syncs. I can add additional information / reservations manually for unconventional items (i.e. a cabin rental)

    I’m curious to know the differences – pros, cons?

    Or Evernote – which also clips, sorts and auto-syncs, but doesn’t put my itinerary together for me.