After 31 consecutive years of work or school, giving myself this summer to leave one job while looking for my next has afforded unique space for lots of productive things, including travel: excluding day trips and overnighters, I was able to see Cabo, Virginia, Connecticut, and Singapore/Kuching, as well as my current annual visit to Orlando/Miami. Travel is, of course, a great privilege and wonderful teacher, so I'm pleased to have made space for a lot of it this year.
It will come as no surprise that I treat travel much like I treat the rest of my life, which is that it is an optimization puzzle to solve. Not that I efficiently script out every minute: even if I had the time for that kind of prep, I think I've grown comfortable with the fine line between exhilaration and terror when I leave some aspects of a trip to chance, not quite knowing in advance how things will play out but finding it fun to figure it out along the way, and roll with good and bad as needed.
But, there is a sense in which travel is a sort of game, in which I have to figure something out based on multiple dimensions. Which is kind of how life works, too. You have to worry about finite time and money. You want to have the best time possible, and maybe do something impactful along the way, whether learning something or giving back or at least not being a total asshole to those whose home turf you're invading.
Of course, different objectives are differently important and different times, which is part of the challenge. I may want to conserve money, but if something really cool presents itself that costs a lot I might still do it. My belly might rumble midday from running myself hard with an aggressive itinerary, but if I can hold off a couple hours and get to a really great spot for food I'll do it instead of settling for something more immediate but less appealing like fast food or a museum cafe.
Here's another fun one I often puzzle over, which is how heavy or light to pack. For 12 days in Singapore, I basically packed 4 days' worth of clothes, and I did 2 1/2 loads of hand-washed laundry mid-trip to recycle those clothes back into good use. It's a pain to hand-wash and it takes up time, but I prefer that hassle over a heavier load. (Of course, one can also find a laundromat, which introduces money and convenience considerations.)
Perhaps the biggest thing to puzzle over is what to see. A lot or a little both have their pros and cons, and assuming you literally can't see everything possible then you have to make some choices about what's worth the time and money. Of course, you can carefully lay your plans and they can blow up in your face: the weather doesn't cooperate, something turns out to be temporarily closed for renovations, or on a more positive note you literally stumble into something completely off your radar screen that is adjacent to somewhere you did have on your itinerary. This too is part of the fun, both in bracing for these uncertainties and then dealing with them in the moment.
Needless to say, travel is one of the finer pleasures in life. I feel lucky to be resourced enough to do it in general, and fortunate that this year allowed me the choice to carve out extended time for multiple excursions. Not every activity was A+ but the whole package was something I'll never forget.

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