Travel Hacks for the 40+ Crowd
Travel tips for people who find themselves googling mobility routines

Happy Jordan Harper Release Week to those who celebrate!
Harper is, at least until SA Cosby drops something new, my favorite fiction writer. He writes crime novels in the mold of James Ellroy and Elmore Leonard but his novels are set in a version of LA that is extremely informed by our moment. His debut novel She Rides Shotgun was adapted into a film last year and around that time I had him on the podcast.
His new novel, A Violent Masterpiece, is out now, and it lives up to the title. I read a preview copy over the winter and am now working through the audiobook. He’s outdone himself. If you’re on Bluesky do me a solid, go find his post and tell him you’d show up if he brought the promotional tour to Tacoma in July.
Subscribe nowWe just got back from a weekend in Dubai. It’s not my favorite city and I’m glad I don’t live there, but it’s a useful escape now and then.
While we were away, the government announced a full week off for the upcoming Eid al-Adha holiday, which marks the end of Hajj and commemorates Ibrahim being tested in the wilderness. The story runs across the Abrahamic traditions, with some variation in the details. In Islam, Allah ordered Ibrahim to sacrifice his son. He was hesitant, but faithful. At the last moment, Allah provided a ram/lamb instead, and Ibrahim became a great patriarch.
As soon as the announcement dropped all the work group chats started popping, and never one to pass up a trip, Hope and I booked four nights in Sri Lanka.
Careful readers are aware of our wanderlust. And at this point, after all our travels, I should have a few hacks; otherwise I’m just a schlub. So this week in light of all that going wrong in the world I want to keep it breezy and offer a handful of tips for my fellow mid-40s traveler. I’m not trying to ostracize younger readers but if hostels still have an appeal to you, this week’s newsletter might not be for you.
For the record, I am neither a passport bro nor a points obsessive, so we’re keeping this fairly basic. But if you want to talk about the benefits and tradeoffs of Chase and Amex eco-systems, I am available by appointment.
Of note, these were refined over breakfast this morning, in consultation with the lovely and gracious Mrs. Bowling.
Listen to the Filipino aunties. I will never read another TripAdvisor review. They’re mostly written by people who had a bad experience and want to rant about the temperature in the room or the proximity of their room to an elevator. The whole site is a graveyard of grudges.
Instead, go to YouTube.
Whatever hotel you’re thinking about booking, a Filipino auntie has made a detailed video about it. I don’t know why they do it, but I’m grateful they do. I’ve even started to notice them in production. If you see Tita Pamela slowly panning across the breakfast buffet and focus on the melon selection, you’re watching magic happen.
They cover everything: check-in, hallways, room feel, even how the place smells. And, crucially, they often talk about how the staff are treated. That matters. In a lot of places, hospitality workers don’t get a fair deal. If someone flags that in a video, take it seriously and move on.
These videos have become a running joke in our house. I used to think they were only a “Filipinas in the Middle East” thing. They are not. Headed to Bourbon Country Kentucky? An auntie has been there. Thailand? Covered. Mexico? Auntie Beth has notes.
Four old local dudes can’t be wrong: We picked this up on the island of Tinos in Greece. Our routine was simple: Greek salad, a shared main, a pitcher of house grapes. You would think those are safe bets. They are not. Quality varies wildly.
One evening, after wandering for what seemed like hours—desperately trying to avoid a tourist trap—we spotted a joint with two different tables of four or five old Greek dudes sitting outside, having the time of their lives. We looked at each other, walked in, knowing we’d found a banger, and the food was incredible.
The rule of four was born.

It’s universal.
If you see four old local guys posted up outside a restaurant or bar, laughing and lingering, that place is worth your time. Those men have known each other for decades. This is their one night of the week out. They are not trying to break the bank or wasting money on mediocre food.
If you’re feeling bold, glance at what they’re eating. They know the menu better than the chef.
This rule has never failed us. Even if we’ve just eaten, if we pass four guys like that twenty minutes later, we’re stopping for at least a small plate.
Never pay for the view. The view at a hotel is great for about thirty seconds. You walk in, put your hand on your hip, and say, “oh, that’s nice.” And then you close the blackout curtains and forget it exists. Hotel rooms are for sleeping.
Paying extra for a view is one of the clearer cons in modern capitalism:
Standard room: $95.
City view: $110.
Mountain view: $125.
Sunset view: $135.
Absolutely not.
I live on the 39th floor with a view of the Arabian Gulf. I can watch the sun come up over the Formula 1 track every morning. I do not need to pay $25 for a slightly better angle on Midtown. If my room overlooks an HVAC unit on the Hyatt next door, that’s fine. I’m there to sleep.
Lastly, invest in relationships. When I was in graduate school, a veteran teacher told us to stay on the good side of two people: the front office secretary and the head custodian. Those are the people who can make or break your day. Truer words were never spoken.
Travel works the same way.
Yes, tip the valet, the concierge, the bartender. That's the baseline. But go a step further. Learn the name of the person working the omelet station. Ask where they’re from. Ask about their family. By day two, homeboy will tell you everything you need to know, including which nearby spots are worth your time and which ones to avoid.
The person making omelets at a hotel breakfast is one of the unsung heroes of the travel economy. It’s a thankless job, and some of the most interesting conversations we’ve had on the road have happened right there at that counter.
Bonus tip: Next time you’re at a hotel breakfast, grab the mediocre-looking waffle and run it through the conveyor toaster. Give it two minutes. What comes out is light-years better than what went in.
If you’ve got goofy or related travel hacks, send them my way. I’m always looking to add to my list and will share them in the next newsletter.
–
Look for a conversation tomorrow on the podcast with “T.” This is my first time having a current student on the show. I interviewed “T” an 18 year-old Palestinian-American woman to get a temperature check on Gen Z and how they’re processing our political moment. I think the conversation is worth your time.