This is interesting because it’s not really about planning, it’s about how much control you want to exert over the experience before it even happens. All of these tools (Google Flights, points systems, loyalty programs) they look like neutral optimizations. But they quietly shape the trip in pretty fundamental ways. You don’t just get a better price, you start making decisions inside the logic of those systems. Routes, timing, even destinations start to converge around what’s easiest to optimize.
I’ve noticed that the more structured a trip becomes upfront, the more similar it can feel on the ground, even across completely different places. Same decision patterns, same cadence, same kind of movement - just different scenery layered on top.
That doesn’t make it worse, just different. More predictable, less friction, but also less exposure to the parts of a place that don’t fit neatly into a plan.
What I like about your piece is that it leans into planning without pretending it’s neutral. It’s a choice about how you want to experience travel, not just how to organize it.
I’ve been writing from the other side of that what happens to places and to your perception of them once those systems start to dominate how you move through the world. Feels like two sides of the same idea. Curious how intentional you are about that trade-off when you plan.
Hmm, thanks for the thoughtful (and thought-provoking) comment! Despite the process I’ve developed, I do also deeply appreciate the unplannable, serendipitous parts of travel. I try to “optimize” for the best experiences, but things regularly surprise me or go wrong. If travel became predictable, I’d enjoy it a lot less. I’m also a bit whimsical about my choices. For example: for my honeymoon, ages ago, I booked a tiny boutique B&B based largely on its cute website (no reviews). As it turned out, I was one of the first foreigners to book a stay there, and the family who owned it were so kind to us. The hotelier’s son even took us out to dinner more than once (we’ve done return trips). So while I did my research to find the place, I couldn’t have planned out that exact experience.
I like your approach to earning and redeeming points and miles. For me, the gamification of the whole process is alluring, but it can easily trap you into complications and overspending. Patience and consistency breeds results. It was a great read, thanks for posting.
I love this framing of travel as a research project. The level of detail (seat maps, neighbourhood-first hotel hunting, spreadsheet outfit planning) is so satisfying. Also agree that structure is what actually creates relaxation. When the logistics are handled, you’re free to notice things. Curious -as there ever been a trip where you tried to “go with the flow” and immediately regretted it?
Good question! Sometimes I plan a bit less, and I feel like I’m not “making the most” of a trip. But logically, I know I don’t need to optimize every vacation. And I want to allow space for serendipity as well, the possibility of stumbling across something I couldn’t have planned for. (Excuse my slow response; still getting the hang of Substack’s feed!)
Great read! I love me some Google Maps! I have at least 20 different lists saved on my maps, and I pin restaurants I read about or am intrigued to try, so when I visit a city, and I'm in a random neighbourhood and starving, I use past Gabby's recommendations on the map! It's saved me many times.
Thanks for all the pointers and tips! I love that you plan it the old school way! It sounds like it takes a lot of time to plan a trip. I’m curious, how long does it take to plan one for you?
Yes to eldest daughter travelling (LOL!) and carry-ons. Loved all these tips, Wing. <3 Also, such a gorgeous shot from Lisbon! Rethinking these small tours now... might need to try one out myself. :) Looking forward to more travel hacks!
Haha, I feel like these tips reveal a lot about my personality. Thank you! The photographer was lovely and just someone I discovered by chance. Travel can be serendipitous that way.
You get it 🤞
I love that!
This is interesting because it’s not really about planning, it’s about how much control you want to exert over the experience before it even happens. All of these tools (Google Flights, points systems, loyalty programs) they look like neutral optimizations. But they quietly shape the trip in pretty fundamental ways. You don’t just get a better price, you start making decisions inside the logic of those systems. Routes, timing, even destinations start to converge around what’s easiest to optimize.
I’ve noticed that the more structured a trip becomes upfront, the more similar it can feel on the ground, even across completely different places. Same decision patterns, same cadence, same kind of movement - just different scenery layered on top.
That doesn’t make it worse, just different. More predictable, less friction, but also less exposure to the parts of a place that don’t fit neatly into a plan.
What I like about your piece is that it leans into planning without pretending it’s neutral. It’s a choice about how you want to experience travel, not just how to organize it.
I’ve been writing from the other side of that what happens to places and to your perception of them once those systems start to dominate how you move through the world. Feels like two sides of the same idea. Curious how intentional you are about that trade-off when you plan.
Hmm, thanks for the thoughtful (and thought-provoking) comment! Despite the process I’ve developed, I do also deeply appreciate the unplannable, serendipitous parts of travel. I try to “optimize” for the best experiences, but things regularly surprise me or go wrong. If travel became predictable, I’d enjoy it a lot less. I’m also a bit whimsical about my choices. For example: for my honeymoon, ages ago, I booked a tiny boutique B&B based largely on its cute website (no reviews). As it turned out, I was one of the first foreigners to book a stay there, and the family who owned it were so kind to us. The hotelier’s son even took us out to dinner more than once (we’ve done return trips). So while I did my research to find the place, I couldn’t have planned out that exact experience.
plane essentials in a bag inside your bag that you can keep at your seat is a KEY tip!!
love this breakdown!! we plan travel so similarly. must be the type a eldest daughter effect!
I like your approach to earning and redeeming points and miles. For me, the gamification of the whole process is alluring, but it can easily trap you into complications and overspending. Patience and consistency breeds results. It was a great read, thanks for posting.
Thank you! I agree. I think travellers can benefit by being strategic, but without getting too deep into the gamification (an apt description)
I love this framing of travel as a research project. The level of detail (seat maps, neighbourhood-first hotel hunting, spreadsheet outfit planning) is so satisfying. Also agree that structure is what actually creates relaxation. When the logistics are handled, you’re free to notice things. Curious -as there ever been a trip where you tried to “go with the flow” and immediately regretted it?
Good question! Sometimes I plan a bit less, and I feel like I’m not “making the most” of a trip. But logically, I know I don’t need to optimize every vacation. And I want to allow space for serendipity as well, the possibility of stumbling across something I couldn’t have planned for. (Excuse my slow response; still getting the hang of Substack’s feed!)
Great read! I love me some Google Maps! I have at least 20 different lists saved on my maps, and I pin restaurants I read about or am intrigued to try, so when I visit a city, and I'm in a random neighbourhood and starving, I use past Gabby's recommendations on the map! It's saved me many times.
Yes! Wise travellers think alike.
Type A eldest daughter here 🙋🏻♀️
Ha, it’s a very specific personality!
Me too! Me too! =)
Thanks for all the pointers and tips! I love that you plan it the old school way! It sounds like it takes a lot of time to plan a trip. I’m curious, how long does it take to plan one for you?
Yes to eldest daughter travelling (LOL!) and carry-ons. Loved all these tips, Wing. <3 Also, such a gorgeous shot from Lisbon! Rethinking these small tours now... might need to try one out myself. :) Looking forward to more travel hacks!
Haha, I feel like these tips reveal a lot about my personality. Thank you! The photographer was lovely and just someone I discovered by chance. Travel can be serendipitous that way.
Travel IS an infinite research project though!
Excellent tip on the shower caps as shoe covers.
I dread to think what you would think of my travel “uniform” 😉, but practical has never been my strong suit.
Thanks for the tips !
Thank you! And I have no doubt your travel uniform is far more stylish than mine.
Oh, that’s a good tip! I haven’t used OpenStreetMap but will check it out. Thank you