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The United States is massive. You could spend a lifetime traveling here and still only see the inside of an airport terminal and a few Marriott lobbies.
Most people get stuck on the “Big Three” rotation: New York for the grit, Vegas for the sins, and Orlando for the Mouse. Those are fine. But if you actually want to understand the scope of this country—the sheer geographical arrogance of it—you need to look slightly to the left of the obvious choices.
If you are building your 2026 travel list, these are the 5 U.S. destinations I genuinely think everyone should experience at least once, because they cover the full spectrum of what this country does best.
PLUS: I’ve built a quiz for you at the end of the article to find your perfect match, so stick around!
Most people fly directly into Key West (EYW), land, and hit Duval Street. That is a mistake.
The reason Key West is on this list isn’t just because of the Hemingway cats or the key lime pie. It’s because of the Overseas Highway.
Driving from Miami to Mile Marker 0 is one of the few American road trips that actually lives up to the movie hype. Trust me, I’ve done it!
You are driving on a thin ribbon of concrete floating over the ocean for four hours. And there are so many great places to stop along the way if you’d rather split the journey up.
One of my faves is The Florida Keys Brewing Company. The beer is fantastic and the vibe is super cool, tons of color everywhere you look, a great outdoor hang space, and more than likely some live music to go along with it.
The Vibe: Caribbean anarchy meets American kitsch.
Perfect For: Couples who want a road trip that doesn’t feel like a commute, and history buffs.
The “Don’t Miss” Experience:
Pro Tip: The seaplane to Dry Tortugas sells out months in advance. If you are planning a trip for late 2026, book this literally today.
Let’s address the elephant in the room: Jackson Hole is expensive. You might pay $25 for a burger. You might pay $800 a night for a “rustic” cabin.
Pay it.
This is the closest thing the U.S. has to the Swiss Alps, but with cowboys. The sheer scale of the Tetons rising out of the valley floor without foothills is something that photos cannot capture. It punches you in the gut.
You can ski to your heart’s content, enjoy hot springs with an epic view, and wrap up your night next to a cozy fire, relishing in the amazing adventures you’ve had.
One of our favorite stays we tested recently was the Wyoming Inn of Jackson Hole. It had the rustic charm you expect from Jackson Hole while offering the luxury of a wellness escape right next to amazing skiing.
The Vibe: Luxury rugged.
Perfect For: Skiers who want to be humbled (Corbet’s Couloir) and summer travelers heading to Yellowstone.
The “Don’t Miss” Experience:
This is going to make some people in the PNW angry. Good.
For decades, Seattle was the undisputed king of the region. But in 2026, the smart money moves to Bellevue. Why? Because Seattle is hosting the FIFA World Cup in June and July. The city is going to be absolute chaos, and hotel prices downtown will be astronomical.
Bellevue is the cheat code. Located just across Lake Washington, it’s a gleaming, high-end metropolis known as a “City in a Park.”
We got to check out Bellevue over the summer and we were completely blown away. You can do everything from full-blown VR game nights to kayaking to a social night out at The W Bellevue.
The Vibe: Futuristic, clean, and aggressively safe.
Perfect For: Travelers who want the PNW scenery without the urban grit.
The “Don’t Miss” Experience:
If you tell a European to visit Minnesota, they will look at you like you’re insane. That’s because they haven’t been to the North Shore.
The 150-mile drive from Duluth to the Canadian border along Highway 61 is arguably the most underrated scenic drive in America. This is Lake Superior.
It is not a lake; it is more like a freshwater ocean. It has cliffs, shipwrecks, and waves that can snap a freighter in half.
The Vibe: Nordic chill. Flannels, craft beer, and cold water.
Perfect For: Hikers and people who are tired of sweating on their vacations.
The “Don’t Miss” Experience:
Santa Fe doesn’t feel like the United States. It feels like a separate republic that decided to outlaw boring architecture. The entire city is adobe; there is a law against glass-and-steel skyscrapers, and thank god for that.
Why 2026? It’s the Centennial of Route 66. Santa Fe is on the original 1926-1937 alignment of the Mother Road, and the city is hosting massive events all year, including the “Railyard Route 66 Centennial Festival.”
The Vibe: Artistic, spiritual, and spicy.
Perfect For: Art lovers and foodies who handle heat.
The “Don’t Miss” Experience:
From the keys to the cliffs. Take this 3-step quiz to find the domestic destination that matches your style.
The “Caribbean Road Trip.” You want history, turquoise water, and zero stress.
The “Rugged Luxury.” You want epic mountains, cowboys, and maybe a $25 burger.
The “Future City.” You want the PNW scenery without the grit.
The “Nordic Escape.” You want cliffs, cold water, and small-town charm.
The “Art & Soul.” You want immersive experiences and distinct culture.
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