5 of the USA’s best road trips (and why you should do them)

written by Elle Hardy October 17, 2018
Road in Shenandoah National Park

The great American road trip has long been a staple of adventure in the Land of the Free.

We take a look five of the United States’ most iconic road trips, with a guide to everything you need for the journey of a lifetime.

1. If you’re looking for kicks, get them on Route 66

Travellers on Route 66

Photo by Phoebe Escott-Kenny

Route 66 — or Mother Road, as it’s sometimes called — is part of American folklore. The road was the first all-weather, continuously paved highway in the country, linking major cities Chicago and Los Angeles. It served as the migration route west from the Dust Bowl depression in the 1930s, spawned much of America’s trademark roadside architecture, and entered into pop culture through songs such as (Get Your Kicks on) Route 66.

In the Best of America road trip, we get on Route 66 in Arizona — after the Grand Canyon, en route to Las Vegas — stopping in the iconic township of Seligman. Its famous Main Street is lined with historic stores chock-full of Americana to ensure that you’ll get your fix of Route 66.


Here at the crossroads of the wild west, grab some homemade beef jerky for the bus ride. The dried, salted meat used to sustain pioneers and people travelling long distances before cars; today it comes in a variety of flavours, and is a natural, low-carb snack for between meals.

Get your kicks on these Route 66 road trips:

2. If you want a dramatic journey from trees to shining seas, take the Pacific Coast highway

Pacific Coast Highway

Photo by Mark Schwettmann

California’s Pacific Coast Highway, a 200-kilometre slither of road, has long attracted dreamers and it’s not hard to see why. This All-American Road — a title reserved for the most historic, scenic parts of the country’s 6.6 million miles of highways — is a staple of bikers and hikers who want to feel the wind in their hair.

You’ve already spent time among the stunning Redwoods, now you can enjoy the views across the Pacific Ocean. Keep an eye out for Bowling Ball Beach near Mendocino, which features perfectly spherical stones all along the sand. The geological wonder is the result of millions of years of concretion, exposing the hard rocks as the cliffs eroded behind them, although some locals like to say that aliens put them there.

Get back to nature on these Pacific Coast adventures:


3. If you like your roads OFF road, take the Overseas Highway

Overseas Highway, Florida

Photo by pisaphotography

U.S. Route 1, some 180 kilometres of highway stretching across the azure waters of Florida Keys, is the southernmost point of the country, and one of the world’s most spectacular stretches of road. The Keys are 34 inhabited islands in a chain of 1,700, geographically closer to Cuba than Miami.

Taking off from Miami, you will head south past the Everglades until can see nothing but a sun-swept sea along the thread that joins these tiny pearls together. Watch holidaymakers and locals fishing and dining, before reaching the final bridge that will make you feel as though someone parted the waters especially for you.

You’ll arrive at the largest island, Key West, perhaps best known as Ernest Hemingway’s home, which he called “the best place I’ve ever been any time, anywhere.” If you need a little help getting into the groove, fire up your playlist with some of Hemingway’s friend Jimmy Buffett, who wrote many of his classic songs in Key West. In the evening, head down to Mallory Square to get an idea of what he meant, with Cuban-American cultures fusing with nightly sunset parties.

Get way down in Florida Keys on these small group adventures:

4. If you want outstanding food and even better music, all roads lead to the Deep South

Bourbon street, New Orleans

Photo by Ryan Bolton

The Americana Music Triangle — Nashville, Memphis, and New Orleans — showcases the best of the Deep South. Here, all roads lead to their famous music strips, where the parties run day and night.

Beginning in Nashville’s Music Row, a collection of honky tonks that offer a rollicking window into the city’s good-time spirit. Do as long-time locals do and soothe your party aches with some soul food at Arnolds, an old-school diner that remains a Nashville favourite in spite of a booming restaurant scene.

A few hours south west, Beale Street in Memphis is the home of the blues, with a bar scene that is made to cure them. From BB King’s electric blues to dueling pianos and spoken word shows, get an introduction to Memphis’ famous wet ribs at Rendezvous or City Barbeque.


On the road from Memphis to New Orleans, look out along the rows of cotton fields that gave birth to the blues. If you fancy a bit of me time, a few podcasts on the area will do the trick: try Uncensored History of the Blues for everything you need to know about the music that began on the Mississippi Delta. For those interested in the history of the Big Easy, the New Orleans History podcast will guide you through the fascinating past of the French colony that remains unlike anywhere else in America.

First time revellers in New Orleans are inclined to head to Bourbon Street, but nearby Frenchmen Street is the place to go for the best jazz bars in town. Grab a to-go cup with your favourite cocktail, and wander between clubs, or stop to grab a po’boy sandwich or dance along with street buskers.

5. If you want to get away from it all, take the Loneliest Road

Lonely highway in the USA

Photo by Phoebe Escott-Kenny

Highway 50, known as the Loneliest Road, begins in San Francisco, passing through the California state capital Sacramento, before linking up to the old Pony Express into the Sierra Nevada, and on to the shores of Lake Tahoe and into Nevada.

The absence of crowds only enhances the beauty of the region. Travel through old gold rush towns and rows of impossibly tall pine trees on your way to reaching the crowning jewels of Lake Tahoe and Yosemite National Park.


This winter wonderland is the perfect place to get stuck into some classic books about the American road. You can’t go past Jack Kerouac’s On The Road, his 1957 novel that heralded a new generation of dreamers. For a change of pace, Cheryl Strayed’s Wild saw her take on the Pacific Crest Trail, which intersects with the Loneliest Road, solo.

To truly understand the importance of the US road, grab a copy of Blue Highways, a seminal book on the American road by William Least Heat-Moon, where he said of the US-50, “this little-known highway is the best national road across the middle of the United States.”

Travel the Loneliest Road on this winter vacay:

Ready for the great American road trip? Explore our full range of small group adventures in the US of A now

Feature photograph by Ryan Bolton.

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