To Plan or To Wing

Family Travel Costa Rica

To plan or not to plan, that is the question. The man and I have polar opposite planning styles. He was much more tolerant of my hyperplanning than I was of his Have-wine-will-travel mantra. His tune hasn’t changed since those early years, while I’ve been on the slippery slope to the dark side ever since.

Family Travel Costa Rica

Our first trip to Europe was for five weeks. The girls were young and the baby was weeks old. Not one night was left unbooked or a day left unplanned. I wanted to max out our entire stay because I wasn’t sure if we’d return. Since that planned-to-the-teeth trip, we also ventured to Paul’s side of the trip-planning pendulum, which is, to not.

The nada-manplan trip happened a few years later. I had in scheduling overload, and he said he’d take care of everything. When we were flying over the Atlantic I asked to see the itinerary. He replied it wasn’t as much of an itinerary but more of a region…of wine. My hyper-planning-wired brain started short-circuiting in so many lobes I had to shut down the main breaker before my mind imploded. I had to do a timeout in the bathroom to keep from getting arrested by an air marshal. I decided the best way to handle it was to somehow keep words from coming out of my mouth and let him deal with the disaster, which would be our summer. I would hire a sky writer on retainer to do “I told you so.” I waited for my glorious gloating moment to be right.

The trip was an outstanding success. One of our best. We would hear of great little towns, decide to rent a house there for a week. We’d extend our stay longer in places we couldn’t get enough of. I thought we had to book houses well in advance, not true. In fact, renting last minute meant we got amazing deals from people who were eager to fill their properties. We stayed in unbelievable villas on the Med for modest amounts. The entire trip was directed by the interests of the group. The kids thought it was fun because we would say, “What country should we stay in next week?” Then we’d discuss. Kid’s vote, winging it. I could have admitted I was wrong, but then that would have been admitting that I was wrong. You planners understand. Luckily the man’s not a gloater or we would have had air marshal issues on the return.

We’ve come to enjoy a certain hybrid of planning and winging it. Every trip to Europe we book the same house in Provence–it’s our favorite. There’s a castle in our backyard, the baker remembers the girls’ favorite treats, Pizza Chris comes weekly, did I mention the backyard castle. After St. Vic, we see where the wind blows us for the remainder of the time. For us it’s the perfect mix of continuing traditions we have already established and the freedom to explore new places as they arise.

I can’t leave without saying the Have-wine-will-travel method of travel does not work in all trip settings. This is especially true when doing a cross-generational, extended family heritage trip with teetotallers like my mom. Those multi-tentacled trips beg for a well-vetted plan, fb group, and something stronger than wine.

For our around-the-world year, we started with a one-way ticket to Costa Rica and a one week condo rental. Now, I’m a non-planning believer to the very core. But that’s another story entirely.