5 American cities I wouldn’t return to after visiting 33 states

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The truth is, I’ve grown to love being home as much as I love traveling. Although my great job at Travel Off Path allowed me to take the leap into digital nomadism, I found myself increasingly playing tourist in my own city.

That said, when I start making travel plans, I take them seriously. That makes it extremely disappointing when something goes wrong, whether it’s a high-end restaurant that doesn’t live up to the hype or everything is going smoothly at a fancy resort until you realize the water pressure is softer than a night with too much whiskey.

It happens…

But what my you-know-what really does is when I get bored on the road, which is typically a foreign concept to me because I’m so independent.

But because of my experiences I have no plans to ever visit these 5 American cities again for one simple reason: they made me appreciate the flight home more than the trip itself.

And just to be clear, I’m not throwing darts at a map because of its content, one of which is my hometown!

My family reunion is about to get very awkward…

Be sure to check the latest travel warnings and entry requirements before your trip.

5) Orlando: No beach, no thanks

Fun fact: Disney World is not in Orlando; it’s in Lake Buena Vista.

Even if that were the case, I would still avoid this city during my travels because I simply cannot fathom the concept of a Florida vacation without a beach in sight.

Since I don’t have kids and don’t feel like dizzying myself with big smiley rodents, the one time I visited Orlando was nothing short of a snoozefest.

Sure, there’s a nice lakeside park downtown, but what else is there other than a mega-popular (albeit very expensive) theme park?

With the nearest worthwhile beach an hour away and picturesque lakes teeming with crocodiles, you won’t find me lounging along the coastline.

Plus, you’d think that with the title “Happiest Place on Earth” it would feel safer. Not so, according to our real-time safety index, which currently ranks it at 75/100.

The best alternative: Carlsbad, California – home to incredible beaches, Legoland and countless chic resorts no more expensive than Disney World

4) Casper: Where the ghost joke writes itself

You know you’re going to take a nap when you’re doing an antelope counting game on the highway just to preserve your sanity.

There were no expectations for Casper, Wyoming, but it was still a dud in my book.

Since we chose to stay in Casper during a road trip to Mt. Rushmore, we couldn’t have picked a better place to catch up on sleep since there’s almost nothing to do other than grab a quick dinner and call it a day.

Was my Airbnb remarkably cheap and spacious? Sure, but exploring the city may have bored me more than the dozens of antelope I counted when I entered.

Casper may be named after Lieutenant Caspar Collins, but it feels quite spooky, just like the cartoon of the same name.

The best alternative: Jackson Hole – it’s pricey, but at least there’s something to do besides sleeping, eating and counting wildlife from the car

3) Dallas: big city, short attention span

Hometown hero? More like hometown zero, if you ask me.

Born and raised on the outskirts of Dallas, I idolized this city like a moth to a flame because I wanted to live in the heart of it, where I could hop aboard the McKinney Avenue trolley and convince myself that I was living a glamorous big-city dream.

Today, with much more worldly experience, I am convinced that Dallas is one of the most overrated cities in America.

Yes, there are some cool museums and trendy bars, but the outlying suburbs and Fort Worth trump Dallas’ endless shopping streets and generous helpings of Tex-Mex, because with the gridlocked traffic of big trucks, it feels like that’s about all there is to do in this city with no culture.

The more I’ve been there in recent years, the more I feel like Dallas has basically become the “Beverly Hills” of the South, where snooty locals care more about their zip code than the city actually has a soul.

Add to that a noticeable increase in crime (with a current ranking of 77/100) and you can bet I won’t be coming home anytime soon.

The best alternative: Fort Worth – a slice of real Texas that makes Dallas feel like a mall with a skyline

2) Colorado Springs: nice rocks, I think

I wish I could say Colorado Springs rocks, but it’s those very rocky formations that are the only highlight of the city.

Technically yes stone – it just rocks too hard.

When oddly shaped boulders are the main attraction, there’s a whole lot of city left to undermine.

Despite being home to almost half a million residents, there isn’t much to do other than take a hike where the landscape doesn’t change from one red rock wonder to another, or grab a ‘local’ beer that’s probably from Golden.

Honestly, my one and only trip to Colorado Springzzz is a distant memory – so much so that I can barely remember it, which shows how boring it was.

The best alternative: San Diego’s Potato Chip Rock – San Diego’s best kept secret, which is much more impressive and a more scenic trek with incredible views that stretch for miles

1) Oakland: There is no speed stick for California’s armpit

Some might say that the armpit of California is Bakersfield, Stockton or Fresno.

For me, it’s definitely Oakland.

Why anyone would spend any time here with San Francisco close by is beyond me, but hey, I tried and wondered why I didn’t just stay across the bay, when even their best attempt at making Jack London Square relevant isn’t worth being called a tourist trap.

I notice a lot of criticism about my love for Mexico and I often say to people who are afraid to scratch their travel itch, “I feel safer in Mexico than in certain American cities” – Oakland is one of the first that comes to mind.

With what seems like more homeless camps than attractions and questionably sanitary restaurants, this city by the bay feels, even to an adventurous foodie like me, past its prime, especially now that all three major sports teams have packed up and left town.

The Warriors moved to San Francisco, the Raiders fled to Las Vegas, and the A’s played their final Oakland season before their planned move to Las Vegas, and the only In-N-Out to ever close its doors due to safety concerns – do you see a pattern here?

The Best alternative: San Francisco is the obvious choice, but don’t skip San Jose for its fewer crowds and surprising attractions that left me wanting more

Take this quiz now to find your perfect alternative!

Sam Sears

Sam, our Senior Lead Writer & Journalist based in San Diego, has visited 44 countries and written more than 1,500 articles with an emphasis on sharing his own travel experiences and highlighting lesser-known gems.