One of our goals with this upcoming adventure is to try to actually NOT plan it all out. I mean, what is a three-month trip good for, if not for allowing us to decide what our next city is on the fly, or to decide to stay somewhere longer than we thought because we’re enjoying the vibe so much?
Now, I know this sounds perfectly obvious to any backpacker, gap-year traveler, or digital nomad, but for us–in mid-career and never having done this before–it’s a bit scary.
I say scary, but we’re not really scared of it. It’s just that we don’t really know how to DO spontaneous.
We started traveling in 1998, and partly because of the era (few if any travel resources online, including booking sites), but also because of our circumstances (a very limited travel budget and vacation time), we were keen on getting the best value, and not wasting time on the ground finding accommodations or figuring out what to see or where to eat.
I became a master at creating lists. Then spreadsheets. In fact, I have a multi-tab travel spreadsheet template I’ve honed over the years, with tabs for our itinerary, expenses, pre-trip to-do list, packing list, and potential restaurants and sights while there.
Oh yes, I’m organized.
But this time around, we’re trying to go with the flow. Somewhat.
We do have our outbound flights, and initial apartment booked, so we have a place upon arrival. (More on that later, including how we decided what city to start with.) And we have the couple weeks around Christmas & New Year’s booked, because that is an extremely popular time of year. Even six months ahead, we had to book two different hotels for that span.
But as for the rest…we’ll figure it out as we go.
Of course, we’re doing our pre-trip research as usual, watching YouTube videos and reading blog posts, marking pages in the various guidebooks to show each other, following good travel Instagram accounts, sending each other links to excursions that look fun. (And I may still have a spreadsheet with a list or two 😉
But we’re not booking anything else before we go, other than our tickets home. Wish us luck!
So, are you a type-a planner or do you show up and figure it out on the ground?
noodlecork 
Figure it out as you go, but I would suggest, as the days draw near, plan to spend the holidays in some place special. My favorite Christmas eve ever was spent in Cuzco, Peru. A potluck Thanksgiving is always a challenge overseas send you discovering interesting footstuffs and maybe some new intimacies with x-pats. We used to throw costume parties in Bogotá and the costume I put together for Halloween entitled me to vocabulary I wouldn’t have learned otherwise. I discovered an amazing garment district in the old city….. Serendipitous explorations and discoveries.
Great suggestions, thank you! Yes, though we are not overly sentimental about being away from home on a particular holiday, we have tried to seek out something interesting and “connected,” in some small way. One year we were in Prague on Thanksgiving and I was delighted to find a turkey schnitzel in an excellent beer hall. Untraditional tradition can be a great memory.