Trip planning is nuts. Every single detail is important. Anything you forget to pack has the potential to mess up your trip, and I know, because someone in my traveling party has forgotten everything including: passport, wallet, car keys, glasses, prescription meds, and hiking boots. There’s even been more than one ticket booked to an airport in the wrong city. Rigor in travel planning is rarely wasted.
The first law of trip planning is: NO CHECKED BAGS.
[The only exception to this is a wilderness trip, because our expedition packs are too big to fit in the cabin, they weigh too much, and we sometimes want to pack liquids].
Personally, I expect the entire sum total of my luggage to fit under the seat in front of me, and usually that’s where I put it.
Why hand luggage? Because you always know where it is, and because you can make connections after a flight delay when others can’t. It also gives you far more options for layover adventures when you don’t have a big wheelie bag - they aren’t even allowed in all places, and you don’t want to find that out the hard way.
NO CHECKED BAGS - NOT JUST A PHILOSOPHY, BUT A RELIGION.
The second law of trip planning: THREE DAYS PER CITY.
We break this rule all the time in small ways, but it is the true foundation of a trip. Three days is enough time to thoroughly explore most cities - too long in my home city, unless you love napping on the beach! Any city that requires more than three days to explore, like London or New York, probably deserves multiple trips. It might also be a good candidate for a hub city.
As an example, we love O’Hare Airport so we route international trips through there whenever we can.
The third law of trip planning: ONE HIGHLIGHT EACH.
A “highlight” is the “swear I’ll never ask for anything else as long as I live” part of someone’s trip. Everyone gets one. The rest of the group better be either ride or die, or they’re going off alone for their own highlight at the same time.
Examples: I rode the London Eye with my husband because it was his highlight, even though I freaking hate Ferris wheels. I owe him for all the times he’s bushwhacked with me in search of, say, the tricolored blackbird, and don’t even ask him about Mandarin ducks.
[Note: I don’t think Mandarin ducks are real. I think they are the Sasquatch of the birding world, added to birdwatching guides as a prank].
Ideally, everyone gets a highlight each day of the trip. Usually they are something small like “buy a bag of Starburst” or “walk across this famous bridge.” In museums, it’s good for each person to pick a room, because the biggest and best museums can’t be covered adequately in a single day anyway.
These are the three laws. They may be amended only after discussion and official approval.
My husband and I also have a policy that we take turns choosing the destination of our trip. We’ve agreed that we would both like to visit every country on Earth, so it’s somewhat arbitrary in which order we see them.
This is when the true trip planning starts.
The very first thing that we do is to check the weather history during the time of our trip. This tends to rule out a lot of ideas. Our wedding anniversary is in late August, which just happens to be a terrible time to travel in large sections of the world. It’s our personal choice to avoid the rainy season, partly because inclement weather means more clothes and bulkier bags.
Next we look at the country’s “national day” and any other major festivals. Usually we are trying to avoid these. They make everything cost 3x as much and almost universally result in large drunken mobs. It can be really fun to see a country decorated for celebration, though.
My next pass - and this falls to me, because I’m the one with the dietary constraints - is to look up as many suitable restaurants as possible. I search for “vegan restaurant” [city] and cross-reference with Happy Cow. Then I mark them all as a favorite on Apple Maps. This is huge because we often wind up in parts of town that we had never anticipated, and we can often find a place to eat nearby without standing on the sidewalk searching for half an hour. Many parts of the world have better options and labeling for gluten-free, vegan, or other preferences or sensitivities than we do in the US. Others do not. It can ruin a trip to discover that the only places with real options for a meal are already closed for the day.
Another vital part of trip planning is to look up “[city] in 24 hours” and “must-see [city]” and “don’t miss [city].” Most of those attractions usually don’t interest either of us at all. A few of them will turn out to be the major highlights of the trip. Sometimes we hadn’t even realized that that attraction existed, and it changes our goals for the trip entirely. I mark all of these in Apple Maps as well.
Once our key attractions and a bunch of restaurants are marked, we zoom in on the map together and browse around. This helps us to get acquainted with the layout of the city in advance. It tends to be pretty obvious that certain places are grouped near each other, and we can spend a day in each area. Other attractions are so far afield that we cross them off our list, not wanting to spend half a day or more on a tour bus unless it’s truly epic.
London wound up happening in pie wedges, with Waterloo as the center of the pie. Iceland happened in loops, starting and ending in Reykjavik.
Spending a few weeks planning a trip adds to the anticipation and extends the fun. It also helps to avoid pitfalls such as showing up on the day that a destination is closed, or arriving so late that we can’t buy a ticket.
Policy is part of trip planning for us. We have a weekly status meeting, where we’ve worked out policies for all aspects of our marriage, and our travel policies have become a friendly, efficient way of having fun together without annoying each other. (Much). The better we get at planning, the more fun we have, and the more we can anticipate our next trip.
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.
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