In the Footsteps of F. Scott Fitzgerald and The Great Gatsby: A Romantic U.S. Road Trip

Few stories capture Jazz Age romance and longing like The Great Gatsby. F. Scott Fitzgerald poured his dreams, heartbreak, and brilliance into the pages, leaving us with a portrait of lavish parties, jazz nights, and the ache of lost love. But Gatsby’s world wasn’t just fiction—it was built from the places and people Fitzgerald knew.

If you and your partner crave a getaway that blends history, style, and a dash of Roaring Twenties charm, let’s set out on a self-driven journey immersed in Fitzgerald’s world. This isn’t just a road trip; it’s a chance to step into a story, together.

Exploring Gatsby’s New York: The Heart of 1920s Glamour

From moonlit mansion lawns to the bright lights of Manhattan, Fitzgerald’s New York drips with promise. The real and imagined places of Gatsby’s universe still beckon couples ready to steal away for romance and adventure—all from the comfort of your own car.

Long Island’s Gold Coast Mansions

Drive east along the tree-lined roads of Long Island, and suddenly, the city’s edge melts into manicured lawns and ornate iron gates. This is the Gold Coast—Fitzgerald’s inspiration for East Egg and West Egg—where old money met new ambition.

Where to Go:

• Oheka Castle—Once a private home, now an upscale hotel. Stroll its gardens or book a night for a Gatsby-style escape.
• Sands Point Preserve—Tour Hempstead House and Falaise Mansion for that grand, echoing-on-marble nostalgia.
• Old Westbury Gardens—The wisteria and reflecting pools seem pulled from Gatsby’s own parties.

Map your own route along Route 25A. Move at your pace, touring mansions in the order you like. Many allow you to wander inside, marvelling at sparkling ballrooms and rich panelling straight from Fitzgerald’s imagination.

Tips for Couples:

• Schedule a private garden tour or picnic.
• Pop into local wine bars in Roslyn or Oyster Bay for an intimate lunch between mansion stops.
• Sunset at the beach near Sands Point is pure magic.

Fitzgerald’s Haunts in Manhattan

Fitzgerald and Zelda lived fast in Manhattan, slipping through champagne-soaked parties, jazz clubs, and posh hotels. This slice of the city holds echoes of their fleeting, passionate nights.

Points of Interest:

• The Plaza Hotel—For a Timeless Gatsby Vibe. Sip cocktails at the Palm Court Bar just like the couple did.
• Algonquin Hotel—A landmark for the city’s writers and artists.
• The Rose Room at the New York Public Library—Impossibly romantic for book-loving pairs.
• Central Park South—A walk here, hand-in-hand, feels like dancing between fiction and life.

Stay nearby, book a jazz-themed suite, or duck into old haunts like Bemelmans Bar for a pre-dinner drink and soft piano music.

Suggestions for Couples:

• Keep an eye out for speakeasy-inspired bars. Some even have password-only entry for a 1920s thrill.
• Plan dinner at a Michelin-starred restaurant, just steps from the Plaza.

Drive Along the Hudson – Jazz Age Road Trip Tips

Leaving Manhattan, the Hudson River unfolds in soft blues and deep greens. This route offered city-dwellers in Fitzgerald’s time a quick escape to grand riverfront estates and leafy hills.

A weekend drive from New York northward rewards couples with ever-changing views and moments that beg for a photo stop.

Recommended Stops:

• Sleepy Hollow—Visit Lyndhurst Mansion or take a riverside walk at dusk.
• Tarrytown—Small cafes, antique stores, and a cosy downtown feel.
• Kingston—Historic streets and river cruises trace the Gilded Age’s flair.

Road Trip Tips:

• Rent a convertible for open-air cruising.
• Stop for brunch at The Tavern at Croton Landing, where locals linger over coffee.
• Plan for spontaneous detours; the scenery calls for it.

Beyond Gatsby: Fitzgerald’s Influences Across America

Fitzgerald’s pen wandered far from New York. To truly capture his story, expand your road trip beyond city lights and mansion gates. This is where the writer’s early joys, heartbreak, and restless spirit come into focus—ideal for couples who see travel as a love letter.

St. Paul, Minnesota: Fitzgerald’s Beginnings

St. Paul is where Scott Fitzgerald grew up—before the fame, the parties, and The Great Gatsby. The rows of grand old houses here seem tailor-made for slow walks and stolen moments. You’ll find the spirit of the novelist on quiet morning streets and in stately architecture.

Places to Visit:

• Fitzgerald’s Childhood Home (599 Summit Avenue)—One of the city’s prettiest neighbourhoods.
• Summit Avenue—Walk or drive beneath leafy trees past some of the best-preserved Victorian homes.
• Commodore Bar & Restaurant—Once a Fitzgerald haunt; perfect for a Champagne toast or cosy dinner.
• James J. Hill House—History meets romance with guided tours.

For Couples:

• Make time for classic afternoon tea at a local bakery.
• Take a leisurely stroll by the river, followed by a sunset picnic.

Montgomery, Alabama: Zelda’s Hometown

No Fitzgerald journey feels complete without a stop in Montgomery, Zelda’s hometown—the birthplace of their Southern love story. The warm air, blooming magnolias, and easy Southern tempo set a relaxed stage for discovering the roots of both artists.

Local Highlights:

• The Fitzgerald Museum—Set in the home where F. Scott and Zelda once lived.
• Cloverdale Historic District—Tree-lined streets and Victorian homes built for meandering.
• Riverfront Park—Gentle walks, river views, and paddleboat rides.
• Zelda’s Childhood Home—Drive by and imagine the early days of their romance.

Tips for a Romantic Visit:

• Try Southern fine dining at Central or Vintage Year.
• Book a carriage ride for two as evening falls.

The Allure of Retracing Fitzgerald’s Footsteps

Traveling in Fitzgerald’s wake is about more than just seeing mansions or sipping cocktails in high-ceilinged rooms. It’s a chance to weave your own story into the fabric of a love affair that has captured readers for generations.

You’ll drift down tree-canopied avenues, lose track of time in golden-lit gardens, and find yourself pausing often—hand in hand—to step back and take in the magic. History hums in these places, blending literary legend, romance, and luxury.

For couples ready to trade the “usual” trip for something both intimate and grand, a Gatsby-inspired road journey offers the perfect escape. Turn up the jazz, pack your favourite book, and let the past lead you to new memories—because the best stories are the ones you live together.