Depending on your arrival time, you’ll be met and transferred to your hotel, where you can take some time to settle in and unwind after your journey. As evening falls, immerse yourself in the vibrant atmosphere of Chicago with a relaxed dinner at one of the city’s excellent restaurants or enjoy a casual visit to a nearby jazz club to soak up the spirit of the Roaring Twenties. It’s the perfect gentle introduction to your Fitzgerald-inspired adventure.

Highlights:

Private transfer from arrival point to accommodation

Settle into your comfortable lodging

Optional low-key jazz bar visit to soak in the city’s musical heritage

Recommended Dining:

The Purple Pig – Mediterranean small plates and wine

Gibsons Bar and Steakhouse– Chicago classic with great steaks

Spend your day fully exploring Chicago’s rich literary heritage and vibrant cultural scene. Start with a visit to the American Writers Museum, where you can enjoy a fast-pass entry to skip the queues and dive deep into the stories of America’s iconic authors.
In the afternoon, wander through Chicago’s independent bookstores, soak up the atmosphere of Millennium Park, or take a relaxing architecture river cruise to admire the city’s famed skyline.
As evening falls, experience the Jazz Age spirit firsthand by visiting one of Chicago’s atmospheric speakeasy bars. Places like The Violet Hour or The Drifter offer expertly crafted cocktails in a vintage setting — the perfect way to immerse yourself in the Roaring Twenties ambiance.

Highlights:
Fast-pass entry to the American Writers Museum

Optional: Architecture river cruise or independent bookstore visits

Optional: Evening drinks at Chicago speakeasy bars like The Violet Hour or The Drifter

Recommended Dining:

Lunch at The Gage — a stylish gastropub in downtown Chicago

Dinner near your speakeasy choice — The Violet Hour also serves small plates

Today, you’ll collect your rental car from downtown Chicago and set out on your adventure. Your first stop is Oak Park, a charming suburb famous as Ernest Hemingway’s childhood home. Visit the Hemingway Birthplace Museum and explore nearby historic streets that inspired some of his early works.
From Oak Park, hit the iconic Route 66, America’s legendary highway, as you head southwest toward Springfield. Along the way, enjoy classic Americana with roadside diners, vintage motels, and nostalgic landmarks that capture the spirit of the open road.
Arrive in Springfield in time to settle into your accommodation and soak in the town’s rich history, famously tied to Abraham Lincoln.

Highlights:

Rental car pickup in downtown Chicago

Optional: Tour of Hemingway Birthplace Museum, Oak Park

Scenic drive on Route 66, exploring roadside Americana

Arrival and evening in historic Springfield

Recommended Stops on Route 66:

Classic diners and vintage gas stations

Small towns with local charm (e.g., Joliet, Pontiac)

Route 66 museums or gift shops

Recommended Dinner in Springfield:

Maldaner’s Restaurant — classic American fare in a historic setting

Obed and Isaac’s Microbrewery and Eatery — local craft beer and hearty meals

Today, you’ll journey south from Springfield to Louisville, making a refreshing stop in Indianapolis along the way. Spend a couple of hours exploring the heart of Indiana’s capital. Visit Monument Circle, the city’s iconic landmark perfect for photos and a short stroll. If time allows, take in the impressive Indiana State Capitol building or enjoy some greenery at White River State Park. A quick coffee or lunch in downtown Indianapolis rounds off this urban pause.
Continue your drive to Louisville, a city steeped in history and famed for its bourbon and Southern charm. Settle into your accommodation and perhaps explore the historic district or enjoy a delicious dinner.

Highlights:

Quick city stop at Indianapolis’ Monument Circle

Optional visit to Indiana State Capitol or White River State Park

Grab coffee or lunch in downtown Indianapolis

Evening arrival and exploration in Louisville

Recommended Dinner in Louisville:

Proof on Main — innovative American cuisine

The Brown Hotel — home of the famous Hot Brown sandwich

Today, you’ll immerse yourself in Louisville’s rich history, culture, and literary connections. Begin with a visit to the Seelbach Hotel, where F. Scott Fitzgerald often stayed — its opulent surroundings are said to have inspired key scenes and characters in The Great Gatsby.
Next, wander through Old Louisville, one of the largest Victorian neighbourhoods in the US. Take in the tree-lined streets and ornate architecture, perhaps pausing for a coffee in one of its charming cafés.
In the afternoon, explore the legacy of Louisville’s most famous son at the Muhammad Ali Center, gaining insight into his extraordinary life and impact. Then head to the Louisville Slugger Museum and Factory to discover the story behind the iconic baseball bat and snap a photo with the world’s largest bat outside.
As the day winds down, enjoy a leisurely stroll through the peaceful, beautifully landscaped Cherokee Park, designed by Frederick Law Olmsted — the perfect spot to reflect on your day.

Dining Suggestion:

J. Graham’s Café – Located in The Brown Hotel, this café is famous for its Hot Brown, a Louisville tradition since 1926.

After breakfast, you’ll head towards Asheville, taking a welcome break in Knoxville, Tennessee — a city rich in Appalachian literary heritage. Known as the home of acclaimed author James Agee, famed for A Death in the Family, Knoxville also boasts a vibrant arts scene centred around the University of Tennessee.
Stretch your legs with a stroll around Market Square, where you can enjoy a coffee or light bite at one of the charming cafés or local breweries. This stop offers a perfect blend of culture and relaxation before you continue your drive into the stunning Blue Ridge Mountains.
Upon arrival in Asheville, check in to the historic Grove Park Inn, a favourite retreat of Fitzgerald’s in the 1930s. As evening falls, unwind with a craft cocktail flight atop Antidote’s rooftop bar, taking in panoramic views of the city and surrounding mountains — an ideal setting for some literary reflection.

Highlights:

Literary pause at Market Square, Knoxville

Explore the Fitzgerald Suite at the Grove Park Inn

Recommended:

Craft cocktail flight at Antidote’s rooftop bar

Spend your day exploring Asheville’s rich literary and artistic heritage. Start with a visit to the Thomas Wolfe Memorial, the childhood home of one of America’s great novelists, whose sprawling autobiographical works capture the spirit of Appalachia.
Wander through downtown Asheville’s eclectic streets, dotted with independent bookstores, galleries, and cafés perfect for soaking up the creative atmosphere that continues to inspire writers and artists today.
For a change of pace, consider a short drive out to the Blue Ridge Parkway for stunning mountain vistas that echo the reflective mood found in Fitzgerald’s later works.
In the evening, treat yourself to dinner at one of Asheville’s renowned farm-to-table restaurants, embracing the local flavours and welcoming vibe.

Highlights:

Visit Thomas Wolfe Memorial

Explore Asheville’s independent bookstores and galleries

Scenic drive or short hike along the Blue Ridge Parkway

Recommended: Dinner at a farm-to-table restaurant

Today, you’ll leave the Blue Ridge Mountains behind and journey north toward Charlottesville, Virginia — a city steeped in history and literary significance.
Along the way, consider a stop in Roanoke, VA, a vibrant city with a rich Appalachian arts and literary scene. Stretch your legs at the Roanoke Public Library or explore downtown’s galleries and cafés, soaking in the local culture.
Arriving in Charlottesville, you’ll find a charming university town known for its connection to American history and literature. Explore the historic University of Virginia, founded by Thomas Jefferson, whose writings and vision shaped the nation.
In the evening, enjoy dinner in the lively downtown area, soaking up the collegiate atmosphere and perhaps catching a reading or live music event.

Highlights:

Stopover in Roanoke: Public library, galleries, cafés

Explore University of Virginia campus

Dinner and evening stroll in Charlottesville’s historic downtown

Begin your day with an optional visit to Monticello, the historic home of Thomas Jefferson. Wander through the beautifully preserved house and gardens, and soak in the legacy of one of America’s most influential writers and thinkers. The estate offers a fascinating insight into Jefferson’s complex life and ideas, making it a perfect literary and historical stop.
After your visit, continue your journey north to Washington, D.C., where you’ll check in to a hotel with a rich literary tradition, such as The Hay-Adams, known for hosting its renowned Author Series, celebrating the written word in style. In the evening, take a leisurely stroll through the atmospheric streets of Georgetown, perhaps stopping by the beloved independent bookstore Politics and Prose for a dose of literary inspiration before calling it a night.

Dinner suggestions:

Old Ebbitt Grill — historic charm with classic American cuisine

The Hamilton — vibrant atmosphere with diverse menu

Spend a full day delving deeper into Washington, D.C.’s rich literary heritage. Begin with a visit to the Library of Congress, the largest library in the world, where you can explore stunning architecture and priceless collections that have inspired countless writers. Don’t miss the Folger Shakespeare Library, home to the world’s largest collection of Shakespearean works and a hub for theatrical and literary events.
In the afternoon, wander through historic neighbourhoods like Dupont Circle or Adams Morgan, known for their vibrant arts scenes and independent bookstores. Be sure to stop by Politics and Prose, one of the city’s most beloved bookstores, offering author talks and a welcoming atmosphere for book lovers.
The evening is yours to enjoy — consider attending a literary reading, play, or simply relax at a café soaking in the city’s creative buzz.

Leave the capital behind and travel north to the picturesque university town of Princeton, New Jersey. Known for its prestigious university and charming streets, Princeton offers a rich literary and academic atmosphere perfect for exploration.
Once you arrive, take time to stroll through the historic Princeton University campus, admiring its stunning collegiate Gothic architecture and visiting the Princeton University Art Museum, which houses impressive collections that have inspired artists and writers alike. Wander through the town’s quaint centre, pop into independent bookstores, and enjoy the relaxed café culture.
In the evening, soak up the small-town charm with dinner at one of Princeton’s excellent local restaurants, reflecting on the literary and intellectual heritage surrounding you.

From Ivy Halls to Gatsby Glamour: A Literary Drive Along Long Island’s South Shore.

After a leisurely morning exploring Princeton, you’ll set off along the stunning South Shore of Long Island. This stretch is famed for its miles of white sandy beaches, lively boardwalks, and charming seaside communities. You might spot the iconic Jones Beach Theater along the way or simply soak up the water-loving vibe.

Whether you’re drawn to fresh ocean-to-table dining, fishing trips, seal or whale watching excursions, or catching a few waves on your surfboard, this area has it all. Just off the coast, the famous car-free summer escape of Fire Island adds a unique charm to the region.

When you arrive at The Quogue Club at Hallock House, you’ll settle into an elegant retreat that perfectly captures the glamour and style of the Gatsby era — the ideal place to unwind and soak up the timeless coastal atmosphere.

Today is all about soaking up the glamour and history of Long Island’s Gold Coast — a region famous for its stunning mansions, beautiful gardens, and that unmistakable Gatsby-era charm.

You might like to start with a visit to Great Neck, a charming town on the North Shore that inspired Fitzgerald’s The Great Gatsby. It’s full of literary history and has a welcoming, vibrant community.

From there, you can explore Sand’s Point Preserve, home to three grand mansions: Falaise, Hempstead House, and Castle Gould. Falaise is a lovely Normandy-style home filled with antiques, famously where Charles Lindbergh wrote WE. The grounds offer lovely views over Long Island Sound and a real sense of stepping back in time.

Another great option is Old Westbury Gardens, an elegant English manor set amid sweeping lawns and immaculate formal gardens. It’s been featured in films like North by Northwest and shows including Sex and the City.

If you’re up for more, Planting Fields in Oyster Bay is a beautiful estate with Tudor Revival architecture, greenhouses, and stunning gardens designed by the Olmsted Brothers. The interiors are full of original art and craftsmanship.

For something a bit different, consider the Suffolk County Vanderbilt Museum, where you can explore a mansion, museum, and even a planetarium — all celebrating Long Island’s rich Gold Coast history.

And of course, there’s the majestic OHEKA Castle, one of the most prestigious historic mansions in the area, offering tours and a chance to enjoy a meal or drink in elegant surroundings.

By late afternoon, you’ll head into Manhattan to drop off your car. The evening is yours to explore — whether that’s enjoying the city’s buzzing nightlife, catching a show, or simply soaking up the unique energy of New York.

Start your day with a two-hour private tour focused on the 2013 film adaptation of The Great Gatsby, based on F. Scott Fitzgerald’s classic 1925 novel. Discover the real-life New York locations where the movie was filmed — from the bustling streets of Manhattan around 1st Avenue and East 59th Street, to the dramatic Queensboro Bridge, and the iconic Plaza Hotel on 5th Avenue.
This visually stunning film, starring Leonardo DiCaprio as Jay Gatsby, Tobey Maguire as Nick Carraway, Carey Mulligan as Daisy Buchanan, and Joel Edgerton as Tom Buchanan, beautifully captures the glamour and tragedy of the Roaring Twenties. The 2014 movie won Academy Awards for Best Production Design and Best Costume Design, among others, making this tour a truly immersive way to experience Fitzgerald’s timeless tale.
Enjoy a leisurely afternoon to explore New York at your own pace. Wander through iconic neighbourhoods, visit your favourite bookstores, or simply soak up the city’s vibrant atmosphere.
Then, as the day winds down, the fun really kicks off. A period vehicle will arrive to collect you for a glamorous evening. Dress up in your best 1920s outfit (optional but highly encouraged!) for a special photoshoot before heading to the spectacular Broadway production of The Great Gatsby.
Experience the glitz, drama, and jazz-age allure of Fitzgerald’s classic brought vividly to life on stage. Your show tickets are included, promising a memorable finale to your literary journey.

Enjoy a final breakfast in Gatsby’s city before departing—or extend your stay. Perhaps take a leisurely walk through Central Park or visit a nearby museum to reflect on your journey through the Jazz Age.
Depending on your flight or train schedule, enjoy some final time in the city to explore, shop, or simply soak up the atmosphere.
When it’s time to leave, your included transfer will take you to the airport or train station, ensuring a relaxed and hassle-free end to your unforgettable literary journey.