The small but thriving town of Tain, situated on the south shore of Dornoch Firth, is Scotland’s oldest royal burgh. Glenmorangie Distillery has been producing its Single Highland malt Scotch whisky since 1843.  Crafting the delicate spirit is entrusted to the legendary Sixteen Men of Tain. from VisitScotland.com

I have a process.  While solo travel is spontaneous, soul-shifting, and sometimes mystical, I have a process.

After that flash of inspiration where on some rainy Friday night with little warning or rational thought about retirement planning I commit to the airline tickets, I start “the plan.”  It is an approach that at its root harbors a fear, a deep fear of freezing in the face of too many choices.

Lowest Common Denominator.  Using a stern, middle school math teacher’s insistence, i look for that lowest commonality – the very basic requirements for my plan.  I sort.  What are the priorities, the real essentials for the trip? As I planned my trip to the Highlands and the Hebrides, what were those non-negotiable experiences?  This took several days of honest thought. At its prime number level, it was castles, Culloden, and the freedom of ferry-hopping. It was also the hope to reclaim that feeling of freedom on the open road adventure that I found on Iceland’s Ring Road, my first solo trip with a car.  Should I happen to stop for a rest break at the scotch distillery, so be it.

So, as Bill Clinton said at the 2012 DNC, It’s ARITHMETIC.

I do not have the infographic, but as I look at the list of all the great places I’d like to see and the must-see essentials, I start to subtract.  Looking at drive times, maps, events to avoid (Mull Road Race), and a real desire to stay at least two nights in each destination, the trip takes shape.  Any spot that isn’t a priority has to be on the wait list.  Any destination that falls too far outside the compass circle of my essential trip, has to wait.

(Side note: I love two nights just because there needs to be one perfect day where you awaken in this place with the day ahead of you, knowing you’ll come back in the evening.  Except Mont St. Michel.  Hear me. One night only. And leave immediately after breakfast. Really.)

The Multiplication.  When the framework of the basic trip is done and the hotels booked (which is by far the best part), I step back.  It’s like the journey itself begins now, long before departure day. As you run through the itinerary in your imagination, there is now the discovery of new possibilities and all the things on the way.

So what do I mean?  Planning that trip to the northwest Highlands, my tickets, hotels, ferry reservations are all made. I find some solid security in that. Now with lots of context and no cares, I start reading, mapping and dreaming. The personal adventure starts to take shape.

A couple of weeks before I left, I was planning  (or dreaming) the route from Stirling to Inverness and realized that the drive time would leave me a full afternoon on arrival in Inverness. I didn’t see that coming – so many drives on this trips were on winding roads but this was highway.  Speed!  I could head right to the Culloden battle field before going into town. What about that one perfect day in Inverness then?  Looking outside my compass circle, I really can take the time to drive to John O’Groats, an easy 2.5 hours up the coast, with beautiful scenery, to the northernmost tip of Scotland. With a free day, I can leave after breakfast and be there before lunch and home for an afternoon stroll before dinner.

Good quickly became great.  There it was! TAIN. The home of my favorite whisky, made by the mysterious sixteen men of Tain.  Right on my way up the coast. An experience I had ruled out is back in and even better now that I have the overall plan.

Life.  Basically, with travel planning, I find pockets of possibility – remembering the adrenaline of travel, learning more about the landscape I’m travelling, checking the drive times, and then the reclaiming of time and surprise and possibility. I know I live my real life very much like that first stage of the plan.  Now, I would like to spend more time living the multiplication stage – the search for possibilities, the constant adding and learning, and new things on the way. Living in the “yes, I can.”

What I Learned

Find a tool that works for you as your trip takes shape. For me, it’s a spreadsheet – for you it might be a vision board, a flow chart or a map. Don’t be afraid to really shuffle it around and look at all the possibilities.  Seeing what it would be like to reverse the trip and drive across mountain passes doesn’t mean you have to…

Leave time along the itinerary when you begin planning.  It’s kind to your future travelling self but it also leaves room to add. It’s far more uplifting to add a great experience than to realize you have to give things up.

Check event schedules.  I planned out the whole Highlands trip and noticed no hotels were available on Mull for my dates. Though normally quiet off-season, my plan A itinerary had landed me in the Mull Road Rally. Luckily, you can reverse the dates on “the plan”.