F. Scott Fitzgerald’s iconic novel The Great Gatsby celebrates its 100th anniversary in 2025 and Northern Kentucky, with its vibrant Prohibition-era past, provides the perfect backdrop for an unforgettable Gatsby-inspired weekend.
From gangster tales and riverboat cruises to rare bourbon tastings, here’s how to revel in Roaring Twenties style while exploring NKY’s storied past — including a link to the real-life Cincy Region man who helped inspire the character of Jay Gatsby.
Newport Gangster Tour
Begin your journey with a Newport Gangster Tour, where history comes alive on the streets of Northern Kentucky’s former Prohibition hotspot. The tour reveals the dark and dazzling underbelly of Newport, considered the original Las Vegas and once nicknamed “Sin City,” showcasing stories of speakeasies, mob bosses and bootlegging empires.
One particularly fascinating figure is George Remus, the so-called “King of the Bootleggers.” Operating just across the river in Cincinnati, Remus became a legend for his extravagant parties and criminal ingenuity. His lifestyle — and his eventual tragic downfall — are widely believed to have inspired Fitzgerald’s creation of Jay Gatsby. One local newspaper even went so far as to proclaim "Another Gatsby Gone" in Remus’ obituary.
As you walk through Newport’s historic streets, it’s easy to imagine the world of Gatsby, where glamour met grit and the American Dream seemed tantalizingly within reach.
Revival Vintage Spirits
No Gatsby celebration is complete without bourbon, and Northern Kentucky — home of The B-Line® passport-guided bourbon tour and gateway to the Kentucky Bourbon Trail® — delivers. Revival Vintage Spirits in Covington is the perfect spot to toast to a century of Gatsby.
Sip on history at this one-of-a-kind bar and bottle shop with a remarkable, ever-changing collection of rare bourbons and vintage spirits, some dating back over a century. Recently expanded into an 8,000-square-foot space, expert guides bring each unique pour to life, from Prohibition-era spirits to sought-after 21st-century classics.
Imagine savoring a flight of vintage bourbons, learning about their history and appreciating their role in shaping Kentucky’s legacy.
BB Riverboats
To truly capture the romance and charm of the Jazz Age, book an evening aboard one of BB Riverboats’ elegant paddlewheelers. The Ohio River played a vital role in Prohibition-era smuggling and trade, making a riverboat cruise a fitting addition to your Gatsby-themed celebration.
Picture yourself gliding along the river under a canopy of stars, the skyline twinkling as you sip on handcrafted cocktails on one of BB Riverboats themed sightseeing or dining cruises.
After your Gatsby-filled weekend in the Cincy Region, continue your literary journey deeper into Kentucky and explore the Seelbach Hotel in Louisville, a favorite haunt of Fitzgerald and the city where the character of Daisy Buchanan was born.
Learn more and book your trip at visitcincy.com.