Most weekend getaways are just expensive ways to feel tired in a different zip code. I spent four hours last Friday sitting in a 2014 Honda Civic that smelled like old fries and damp floor mats just to see a tree. Well, a lot of trees. But by the time I got to the “scenic” overlook in the Catskills, I was so annoyed by the traffic on the New York State Thruway that I didn’t even want to look at the foliage. I wanted to fight the foliage.

We’ve been sold this lie that a weekend trip needs to be this curated, high-production-value experience. You see the Instagram posts of people in linen shirts drinking natural wine in a meadow. What you don’t see is the 114 minutes they spent looking for a parking spot in Hudson, NY, or the fact that their “luxury cabin” was actually a glorified shed with a leaky roof that cost $412 a night plus a $150 cleaning fee. I know because I was that idiot last October. The roof leaked right onto my pillow at 3:00 AM. It felt like the universe was spitting on my poor financial decisions.

The Hudson Valley is a beautiful trap

I’m going to start with a take that might get me blocked by half the people I know: Hudson, New York, is a theme park for people who work in marketing. It’s lovely, sure. The brick buildings are perfect. The antiques are overpriced in that very specific way where you feel poor just looking at a mid-century chair. But it’s exhausting. You have to make dinner reservations three weeks in advance for a place that serves “deconstructed” carrots.

If you’re going to do the Hudson Valley, go to Kingston instead. Or better yet, just keep driving until the coffee shops stop having logos designed by a boutique firm in Brooklyn. I used to think the “curated” experience was what I wanted. I was completely wrong. What I actually wanted was a place where I could buy a $9 breakfast burrito and sit on a bench without someone filming a TikTok in my peripheral vision.

Real travel isn’t about the aesthetic; it’s about the lack of emails.

Anyway, I digress. My point is that the most popular weekend getaway locations are usually the ones that require the most work to actually enjoy. It’s a paradox. You’re traveling to relax, but the logistics of the trip itself create a baseline level of cortisol that negates the entire point of the vacation.

Why I actively tell my friends to avoid Nashville

I know people will disagree with this, but Nashville is a nightmare. I refuse to go back. I don’t care if your cousin had a great time at a bachelorette party there; Broadway is just a neon-soaked hellscape of “Woo!” girls and overpriced domestic beer. It feels like a country-music-themed version of Times Square. If I wanted to be surrounded by screaming strangers and smell stale vomit on the sidewalk, I’d just stay in New York and ride the L train at midnight. It’s cheaper.

There is nothing authentic about a city that has turned its entire downtown into a stage set for tourists. I’m sure there are great neighborhoods in Nashville—I’ve heard East Nashville is cool—but as a weekend getaway location? No. Unless you enjoy waiting in a 40-minute line to take a picture in front of a wing mural, stay away. Total waste of a flight.

The “Boring” Mid-West Win

I might be wrong about this, but I think the best weekend I’ve had in the last three years was in Galena, Illinois. It has a population of about 3,200 people. It’s mostly just 19th-century brick buildings and a river that looks like it’s barely moving. There is absolutely nothing “cool” about it in a modern sense.

• The hills are surprisingly steep (I tracked a 14-degree incline on one walk).
• The main street is full of shops that sell things like jam and handmade candles.
• You can actually hear yourself think.

It’s boring. And that’s why it works. When there’s nothing “must-see” on your list, you actually end up doing things you enjoy. I spent four hours reading a book in a park. I didn’t take a single photo for my grid. I just existed. The traffic out of the city is like a slow-motion heart attack, but once you get past the Chicago suburbs and the cornfields start to roll, the pressure just drops.

What I mean is—actually, let me put it differently. We go on these trips to escape our lives, but we usually just bring our high-strung, achievement-oriented brains with us. We try to “win” the weekend by seeing the most stuff. Galena doesn’t let you win. It just lets you be.

The Savannah Humidity Factor

If you want something with more flavor, Savannah, Georgia is the only “popular” spot I’ll defend. But only if you go in the off-season. If you go in July, Savannah feels like being hugged by a warm, wet wool blanket. It’s suffocating. I’ve tested this—I’ve been there in July and I’ve been there in November. In November, it’s a dream. In July, I wanted to peel my own skin off just to get a breeze.

The city is laid out in a grid of 22 squares. It’s impossible to get lost, which is great because I have the directional sense of a concussed pigeon. You can walk the entire historic district in a 14-block radius. The moss is beautiful, the history is dark and weird, and you can walk around with a drink in your hand. It’s the only place where the “tourist trap” elements actually feel earned because the architecture is so genuinely stunning.

I have an irrational hatred for Moxy hotels, though. They try so hard to be “edgy” with their check-in desks at the bar and their “playful” lobby games. I stayed at one in a similar city and the room was so small I had to move the chair just to open the bathroom door. Never again. Give me a dusty old B&B with a creaky floorboard and a host who talks too much about ghosts any day. At least it has a soul.

How to not ruin your own trip

Stop over-scheduling. That’s the whole trick. If you have more than two “planned” activities per day, you’ve already failed. The best moments of any trip are the ones where you stumble into a dive bar that doesn’t have a cocktail menu or find a trail that isn’t on AllTrails.

I used to spend weeks researching. I’d have spreadsheets. I’d track gas mileage and average meal costs. Now? I pick a direction, drive for four hours, and see what happens. Sometimes it’s a disaster. Sometimes I end up in a town where the only place to eat is a gas station that sells fried gizzards. But at least it’s my disaster, not a pre-packaged one I bought from a travel influencer.

I honestly don’t know why we feel the need to leave our houses every time we have 48 hours of free time. Maybe we’re all just desperately trying to outrun our own boredom. Or maybe we just need to see a different set of walls for a while so we can appreciate our own couch when we get back.

Go to Galena. Skip Nashville. Don’t stay in a shed.