In Their Footsteps: An Ernest Hemingway Road Trip Across America and Beyond

There are few names in twentieth-century literature that conjure an image as potent as Ernest Hemingway. The name itself seems to carry the scent of salt water, Cuban cigars, and old whiskey. He was more than a writer; he was a force of nature, a man who lived as hard as he wrote, and whose life was a grand, sprawling adventure that crisscrossed the globe. For the modern traveler with a literary soul, there is no better guide to a life of passion, purpose, and relentless exploration. This is not just a journey to the places he lived, but a pilgrimage into the very heart of his work, a perfect addition to any literary travel itinerary.

Born at the turn of the century in the conservative, affluent Chicago suburb of Oak Park, Illinois, on July 21, 1899, Ernest Miller Hemingway’s story begins not in the sun-drenched landscapes of his novels, but on the quiet, tree-lined streets of Victorian America. His father, a well-respected physician, and his mother, a trained opera singer, instilled in him a love for both the arts and the outdoors. Summers were spent at the family’s cottage on Walloon Lake in Michigan, where a young Ernest learned to hunt, fish, and camp—skills that would later define his public persona and permeate his fiction. It was here, in the wild heart of America, that the seeds of his adventurous spirit were sown, making it a key stop on any Hemingway trail.

But the quiet life was never destined to hold him. After a brief stint as a reporter for The Kansas City Star—where he first learned the value of short sentences, active voice, and clarity—Hemingway volunteered for the Red Cross in World War I. His experiences in Italy, where he was severely wounded and fell in love with a nurse, would become the crucible in which his literary voice was forged, providing the raw material for his 1929 masterpiece, A Farewell to Arms. This novel, a heart-wrenching tale of love and loss set against the brutal backdrop of the war, cemented his status as a literary powerhouse.

His travels, however, had only just begun. The “Lost Generation” of the 1920s found him in Paris, where he honed his craft alongside Ezra Pound and Gertrude Stein. He fell in love with the bullfights of Pamplona, Spain, an obsession that would lead to his first great novel, The Sun Also Rises (1926). He covered the Spanish Civil War as a correspondent, an experience that gave birth to the epic For Whom the Bell Tolls (1940). And, of course, he made a home in the sun-drenched, salt-sprayed landscapes of Key West, Florida, and Cuba, where he wrote his Pulitzer and Nobel Prize-winning novella, The Old Man and the Sea (1952). This deep connection to place is why a Hemingway tour is so compelling.

To follow in Hemingway’s footsteps is to embark on a journey that is as much about the man as it is about the places he inhabited. It is a road trip USA adventure through the heart of America and beyond, a journey that takes you from the quiet suburbs of Chicago to the tropical paradise of the Florida Keys, from the rugged mountains of Idaho to the vibrant streets of Havana. It is a journey for the adventurous, the curious, and the literary-minded. It is a journey for those who, like Hemingway, believe that “it is good to have an end to journey toward; but it is the journey that matters, in the end.”

The Hemingway Road Trip: An American Odyssey

This road trip is designed as a journey through the American landscapes that shaped Hemingway, from his birthplace to his final resting place. It is a journey that can be taken in its entirety or in individual segments, each offering a unique glimpse into the life and work of this literary giant.

Stop 1: The Beginning - Oak Park, Illinois

Our journey begins where Hemingway’s did: in the historic Chicago suburb of Oak Park. This is where you’ll find the roots of the man, the place where his story began. A visit here provides essential context for the American author tour that lies ahead.

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Things to Do in Oak Park

Your first stop should be The Ernest Hemingway Birthplace Museum at 339 N. Oak Park Ave. Stepping into this beautifully restored Queen Anne home is like traveling back to the turn of the century. The guided tour offers a fascinating glimpse into his early life and the Victorian world that shaped him. Afterward, head to The Hemingway Museum at 200 N. Oak Park Ave., located in the former Arts Center. It features exhibits on his entire life, from his childhood to his time as a war correspondent and his ultimate literary achievements. Finally, take a walk through the historic neighborhood to see the other homes where Hemingway lived, including the house at 600 N. Kenilworth Ave., which his mother designed. The area's architecture, featuring many Frank Lloyd Wright homes, is a sight to behold in itself.

Where to Stay:

Hotels in Oak Park
Where to Eat

For a stay steeped in local history, consider The Carleton of Oak Park, a historic hotel with modern amenities right in the heart of the village. Prices start around £150 / $204 per night. Alternatively, the Harvey House Bed & Breakfast offers a charming and more intimate experience in a historic home, with prices starting around £120 / $163 per night.

Stop 2: The Writing Retreat - Piggott, Arkansas

From the bustling suburbs of Chicago, our journey takes us south to the quiet, rural town of Piggott, Arkansas. It was here, at his second wife Pauline Pfeiffer’s family home, that Hemingway wrote parts of A Farewell to Arms in a converted barn. This is a place of quiet contemplation, perfect for connecting with the writer’s process. The main attraction is The Hemingway-Pfeiffer Museum and Educational Center, where you can tour the family home and the barn studio. The museum offers a fascinating look at this lesser-known but highly productive period of his life.

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Things to do in Piggott

Where to Stay:

Hotels in Piggott
Where to Eat

Accommodations are cozy and welcoming at The Inn at Piggott, located just a short walk from the museum. Prices start around £80 / $109 per night.

Stop 3: The Island Paradise - Key West, Florida

Now, we head to the sun-drenched, rum-soaked island of Key West, Hemingway’s home from 1931 to 1939. This is where the legend of “Papa” Hemingway was born—a place of fishing, drinking, and writing. It is, in many ways, the spiritual heart of the Hemingway trail and a must-do for any Florida Keys travel plan.

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Things to do in Key West

No trip to Key West is complete without visiting The Ernest Hemingway Home and Museum at 907 Whitehead St. Wander through the rooms of this iconic Spanish Colonial home where Hemingway wrote some of his greatest works, and be sure to say hello to the famous six-toed cats, descendants of his own feline companions. Afterward, head to Sloppy Joe’s Bar on the lively Duval Street (201 Duval St.), a Key West institution and Hemingway’s favorite watering hole. Pull up a stool, order a Papa Doble (Hemingway’s signature daiquiri), and soak in the history. To truly walk in his footsteps, charter a boat and head into the Gulf Stream, just as Hemingway did. The experience of being on the water that inspired The Old Man and the Sea is unforgettable.

Where to Stay:

Hotels in Key West
Where to Eat

For luxury, the Casa Marina Key West, Curio Collection by Hilton is a stunning oceanfront resort with a private beach. Prices start around £400 / $544 per night. For a more intimate and romantic experience, The Gardens Hotel is a beautiful, tranquil hotel set in a lush botanical garden, with prices starting around £300 / $408 per night.

Stop 4: The Final Frontier - Sun Valley, Idaho

Our final stop takes us to the rugged, majestic mountains of Sun Valley, Idaho. This was Hemingway’s final home, a place where he could hunt, fish, and find a measure of peace in his later years. It is a place of stunning natural beauty and quiet reflection, a fitting end to a USA road trip of this magnitude.

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Things to do in Sun Valley

Visit The Hemingway Memorial, a simple, moving tribute located on a quiet trail overlooking Trail Creek. The inscription reads: “Best of all he loved the fall, the leaves yellow on the cottonwoods, leaves floating on the trout streams and above the hills the high blue windless skies… now he will be a part of them forever.” You can also pay your respects at Ketchum Cemetery, Hemingway’s final resting place, marked by a simple flat stone. Finally, explore the outdoors by hiking, biking, or fishing in the same mountains and streams that Hemingway loved, connecting with the natural world that so inspired him.

Where to Stay:

Hotels in Sun Valley
Where to Eat

The Sun Valley Lodge is a classic, luxurious resort with a rich history and stunning mountain views, with prices starting around £350 / $476 per night. For a more modern option, the Limelight Hotel Ketchum is a stylish hotel with a lively atmosphere in the heart of Ketchum, with prices starting around £250 / $340 per night.

Beyond America: Hemingway’s International Haunts

While our road trip focuses on Hemingway’s American journey, no exploration of his life would be complete without a nod to the international locations that so profoundly shaped his work.

· Cuba: Hemingway lived in Cuba for over 20 years, and his home, Finca Vigía, is now a museum. A visit to Havana offers a glimpse into the world that inspired The Old Man and the Sea.

· Spain: From the Pamplona bull run to the battlefields of the Spanish Civil War, Spain was Hemingway’s spiritual home. A trip to Madrid and the Basque country is a must for any true Hemingway aficionado.

· France: The Paris of the 1920s was the backdrop for Hemingway’s formative years as a writer. A walk through the Latin Quarter, with a stop at Les Deux Magots or Café de Flore, is a journey back in time to the era of the Lost Generation.

A Final Word

To travel in the footsteps of Ernest Hemingway is to embrace a life of adventure, to seek out the authentic, and to find beauty in the raw, unfiltered experiences of the world. It is a journey that will take you to the heart of America and beyond, a journey that will leave you with a deeper understanding of the man, his work, and the world that he so passionately embraced. So pack your bags, grab a good book, and hit the road. The adventure of a lifetime awaits.

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