Put this in the category of Problems Everyone Should Have. One day, you find yourself with enough time, money, permission, and inclination to fulfill a dream… and you have no idea what to do. Solving all your problems has a tendency to dispel that level of tension that used to generate so many plans and fantasies. “Travel to Europe” has been on my bucket list since I was 10 years old. Suddenly, it’s time to get specific. What to do? What to do?
We start with two constraints: the timeline and the starting point. There is a trade show in a particular city. When the show is over, we have two weeks to play. Where should we go? I order a European travel guide (using Powell’s store credit) and wait impatiently for it to arrive.
We start by considering the country that is hosting the trade show. We quickly decide that, while we very much want to explore this place, we want to do it in summertime, when we can hike, camp, and sleep in our three-season tent. We’re not ruling it out; we’re setting aside a rough mental sketch of a different potential future trip.
This leads to the easy decision to choose a place that will be warm at this particular time of year. We are sissies about this. We live south of every city in Europe, plus most of Asia and North America. We live in perpetual summer. We can expect that if we want to go anywhere, it will probably rain a lot, but surely no more than necessary? We are also tightwads, and we prefer the known quantity of our tent (the Hotel Denham) to the unknown quantities of hostels and hotels.
My experience of a trip revolves entirely around the choice of mattress. I have a major parasomnia disorder, and it doesn’t take much to throw my sleep schedule into chaos. Within a few days, I’ll be a walking trainwreck of exhaustion, headaches, leg spasms, irritability, and distraction. That’s if we’re lucky and I don’t wind up standing in the middle of the bed, unconsciously slapping myself and screaming. In other words, it’s better for everyone if I take care of myself. That means either a comfortable mattress with a deep pillow top, or my familiar sleeping bag on top of my familiar air mattress. No point taking halfway measures, sharing a room with strangers or sleeping on a two-star monstrosity. (Mattrosity?) Other people will find that the make-or-break factor of a good trip is access to special food, medication, high-end walking shoes, contact with at-home family, or something else that is highly personal. For me, it’s sleep, and it would be irresponsible for me to plan otherwise.
We hit a speed bump when I become curious about a particular country and start looking closely at the rail map, only to find that my honey doesn’t really want to go there. We are mutually surprised that we didn’t both instantly hit on the same idea, the way that we did with Iceland. (We were on our honeymoon in Victoria, BC, talking about where to go next, and we were both like, DUH, ICELAND!). Then I decide, in a classic case of sour grapes, that my language skills for the vetoed country aren’t very strong anyway. Might as well save that place for a different year as well.
We agree on the obvious, which is the place we were most recently considering for a vacation. The trip we intend(ed) to take requires five weeks to do it properly. For several reasons, this is not the year for that trip. There were other regions we knew we would miss on the five-week version. Why not do one or more of those on this trip? This sounds like a plan, and I order a more specific travel guide for this country (using a gift card).
Next, we decide on transport. We’re flying in separately, since there is no point having me hang around the hotel room during the trade show while expensively boarding our animals for the extra days. We’ll fly back together. We’ll take the train to our destination country. That part of the trip is a hazy cloud of intention, lacking shape or detail, so we choose an exit city and plan a day to get there. We book plane tickets. Now we know we’re arriving in one city and leaving from another that is hundreds of miles away.
I read the section in the all-Europe guide about our intended country, and make note of all the top-scored cities. Might as well start there. The guidebook suggests a range of days for each city, from one to three. We tend to agree. After I start sketching in the finer details of the trip, it emerges that the guidebook does not cover one of the country’s major cities. I have to Google to find out why. Although it looks like an obvious point on the rail map, the high-speed rail bypasses it. We can still get there quite easily; we’ll just have to do our own independent research (or consult a different brand of guidebook) to find out what to see.
I have a Pinboard of this country from last year. I go through it and locate all the beautiful pictures on the national map. It transpires that almost everything I picked is in the wrong part of the country. We are now up to at least three completely distinct iterations of fabulous dream vacations in this country. An embarrassment of riches. I read that people often return to this place, which seems like a good sign. We’d go to Iceland again; we know how we would spend an entirely different three weeks next time. This sense of depth and richness, too much to explore in the time allotted, adds a layer of anticipation and sparkling potential to our plans. Rather than FoMO, it’s more like adding a sense that we’re following the Yellow Brick Road without yet knowing what is down the other colors of brick pathways.
I make an index card for each of the cities in my rough draft of our trip. I write the city’s name, the estimated number of days from the guidebook, whether they have campsites and vegan restaurants, and the attractions that are most likely to interest us. We don’t need to bother with kids’ activities; we don’t do wine tours, bars, or nightclubs; we don’t like package tours; we have very particular taste in museums. A nautical museum rated as ‘boring’ in the guidebook would probably be right up our alley. We love archaeology. Part of our friendship is based on our mutual interest in several eras of history, and we know we won’t be selfishly indulging ourselves by boring each other. That’s my job on Birdwatching Day. (The worst part about birdwatching together is that he’s better at it; he spotted his first ptarmigan days before I saw mine).
I show the index cards to my honey. I explain about the missing major city, and that we’ll have to figure out for ourselves how many days to spend there. We look at the map together and realize that one of my picks, a major three-star city, is quite a distance from all the others. He suggests that we postpone it and add it as the starting point of the five-week dream trip. Yay! This idea is a classic example of how I tend to make things needlessly complicated, and then he takes one look and simplifies it in the best way. I am so relieved. The days add up correctly. Travel times between each of our cities are roughly the same. We started with a total blank, and now we have a plan that makes sense.
There is still a lot left to do, but the broad sketch is there. You can tell what it’s supposed to be. I am the planner on our team; he books the tickets, rooms, and rental cars, while I figure out where to go, what to do, and what to eat. I also get the house ready and plan the packing lists. These tasks are divided by aptitude, but also by our personal desire to have control over these areas. I developed a method during our big Iceland trip, one that turned out to have some glaring flaws and blind spots, and we learned a lot. We learned how much we overpacked. We learned how important it is not to use a half-price four-year-old guidebook. We learned that we each need our own copy of my extensive spreadsheets, maps, and checklists. We learned to map out the grocery store in each town. We learned how far in advance we need to be training physically if we want to carry our packs comfortably and avoid blisters.
The next step is to sit down with a calendar, a rail map, and a train schedule. I’ll mark which attractions are closed on particular days of the week. I’ll figure out whether any major festivals or events are coming up, and whether to try to attend or avoid them. For each town, I’ll figure out which sites we can see on the same day and what order we’ll see everything. I’ve already looked at estimated average temperatures for the time of year, and I’ve realized that I don’t have enough appropriate clothes right now. While I’m mentally spinning a capsule wardrobe, I’m also trying to narrow down which book to bring on the flight. It’s starting to look real.
I’ve made this post as vague and abstract as possible. I’ll post where we actually went after the trip is done, since that seems safer. More importantly, I wanted to talk about the planning stage of a trip, for those who have even less experience than I do. (My husband and I have been together for ten years, and this will be our fourth major trip together. It’s only the second trip that will last more than five days). I’ve been flying alone since the age of 7, and my hubby and I are both experienced at camping and going on road trips together. Our familiarity with each other is responsible for about half our fun; the preparation covers the other half. We never want to be like the couple we overheard screaming at each other for two days during our honeymoon: “What KIND of a person… FORGETS a BAG?!?” The more systems we build, the more we put on autopilot, the more we can trust ourselves and each other… and relax.
I've been working with chronic disorganization, squalor, and hoarding for over 20 years. I'm also a marathon runner who was diagnosed with fibromyalgia and thyroid disease 17 years ago.