The truth is that I’ve grown to love being home just as much as I love traveling. While I could take the plunge into digital nomadism thanks to my awesome job at Travel Off Path, I’ve found myself playing tourist in my own city more and more.
That said, when I do begin making travel plans, I take them seriously. That makes it ultra-disappointing when things go awry, whether it’s a top-rated restaurant not living up to the hype or everything going flawlessly at a posh resort until you realize the water pressure is softer than a night of too much whiskey.
It happens…
But what really chaps my you-know-what is when I find myself bored on the road, something that’s typically a foreign concept to me, being so independent.
However, because of my experiences, I have no plans to ever visit these 5 U.S. cities again for one simple reason: they made me appreciate the flight home more than the trip itself.
And just so you know, I’m not throwing darts at a map for content’s sake, one of them is my hometown!
My family reunion is about to get really awkward…
Be sure to check the latest Travel Alerts & 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 it was, I would still shun this city from my travels because I just can’t grasp the concept of vacationing in Florida without a beach in sight.
Having no kids and no desire to giddy myself with smiley oversized 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 closest worthwhile beach being an hour away and scenic lakes filled with gaggles of gators, you won’t catch me lounging along the shoreline.
Plus, with the title of “Happiest Place on Earth”, you’d think it’d 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 numerous posh resorts no more expensive than Disney World
4) Casper: Where The Ghost Joke Writes Itself
You know you’re in for a snoozer when you create an antelope-counting game on the highway just to keep your sanity.
There were zero expectations for Casper, Wyoming but it was still a dud in my book.
Opting to stay in Casper on 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 but grab a quick dinner and call it a night.
Was my Airbnb remarkably cheap and spacious? Sure, but venturing into town may have bored me more than the dozens of antelope I counted driving in.
Casper may be named after Lt. Caspar Collins, but it feels quite ghostly, just like its namesake cartoon.
The Best Alternative: Jackson Hole — it’s pricey, but at least there’s something to do besides sleep, eat, and count wildlife from the car
3) Dallas: Big City, Short Attention Span
Hometown hero? More like hometown zero, if you ask me.
I was born and raised on the outskirts of Dallas and used to idolize this city like a moth to a flame, wanting to live in its heart, where I could hop aboard the McKinney Avenue trolley and convince myself I was living a glamorous big-city dream.
Nowadays, with way more worldly experience, I’m convinced Dallas is one of the most overrated cities in America.
Yeah, there’s some cool museums and trendy bars, but the outlying suburbs and Fort Worth are outshining Dallas’s endless shopping and generous portions of Tex-Mex, because with its gridlock traffic of oversized trucks, it feels like that’s just about all there is to do in this city lacking culture.
Over recent years, the more I’ve visited, the more I feel like Dallas proper has become the South’s “Beverly Hills”, where snooty locals care more about their zip code than the city actually having a soul.
Factor in a noticeable uptick in crime (with a current ranking of 77/100) and you can count me out from coming back home any time soon.
The Best Alternative: Fort Worth — a slice of real Texas that makes Dallas feel like a shopping mall with a skyline
2) Colorado Springs: Nice Rocks, I Guess
I wish I could say Colorado Springs rocks, but it’s those very rocky formations that are the lone highlight of the city.
Technically, it does rock — it just rocks too hard.
When oddly-shaped boulders are the main attraction, that leaves a whole lot of city left to underwhelm.
Despite being home to nearly half a million residents, there’s just not much to do except go on a hike where scenery doesn’t change from one red-rock wonder to another, or grab a “local” beer that likely came from Golden.
Truth be told, my one trip to Colorado Springzzz is a distant memory — so much so that I barely remember it, showing just how much of a dull blur it was.
The Best Alternative: San Diego’s Potato Chip Rock — San Diego’s best-kept secret that’s way more impressive and a more scenic trek with incredible views stretching miles and miles
1) Oakland: There’s No Speed Stick For California’s Armpit
Some might say California’s armpit is either Bakersfield, Stockton, or Fresno.
To me, it’s undoubtedly Oakland.
Why anyone would spend any time here with San Francisco close by is beyond me, but hey, I tried it and left wondering why I didn’t just stay across the Bay, when even their best attempt of relevancy Jack London Square isn’t worth being called a tourist trap.
I catch a lot of flack for loving Mexico and oftentimes I tell people who are afraid to scratch their travel itch that “I feel safer in Mexico than certain U.S. cities” — Oakland being one of the first that comes to mind.
With what seems like more homeless encampments than attractions and questionably sanitary restaurants, even for an adventurous foodie like me, this bayside city feels past its prime, especially now that all three of its major sports teams have packed up and left town.
The Warriors moved to San Francisco, the Raiders bolted to Las Vegas, and the A’s played their final Oakland season before their planned Las Vegas move, and the only In-N-Out to ever close shut its doors due to safety concerns — see a pattern here?
The Best Alternative: San Francisco is the obvious choice, but don’t skip San Jose for fewer crowds and surprising attractions that left me wanting more
Now take this quiz to find your perfect alternative!
Question 1 of 4
What’s your ideal vacation setting?
Question 2 of 4
What is your preferred activity?
Question 3 of 4
What do you want to avoid most?
Final Question
Pick your perfect evening:
Carlsbad / San Diego, CA
The SoCal Coastal Escape
Pro Tip: Head to Carlsbad for incredible beaches, posh resorts, and Lego Land, or trek to San Diego’s Potato Chip Rock for views that stretch for miles.
Jackson Hole, WY
The Mountain Upgrade
Pro Tip: Jackson Hole might be pricey, but it offers world-class wildlife, deep nature, and upscale lodges with endless things to do beyond just sleeping.
Fort Worth, TX
Authentic Texas Culture
Pro Tip: Fort Worth offers a real slice of Texas. Ditch the big-city gridlock and dive into genuine local history, incredible food, and a city with actual soul.
San Jose, CA
The Bayside Gem
Pro Tip: Skip the armpit of California and head to San Jose (or cross the bay to San Francisco) for surprising attractions, fewer crowds, and amazing local food.
