PRIME TIME™ Travel presents...

The Great Gatsby 100th Anniversary Tour

September 1 - 4, 2025

Immortalized in “The Great Gatsby”, the Hamptons have long been the summer getaway for the rich and famous.
Charming waterfront villages, world-class wineries and beautiful beaches are just a few of the many highlights of this magical place.

This year marks the 100^th anniversary of F. Scott Fitgerald’s timeless classic, The Great Gatsby. Step back in time to the dazzling world of the Roaring ‘20s with PRIME TIME™ as we celebrate this grand occasion on our Great Gatsby 100^th Anniversary Tour scheduled September 1-4, 2025. From the bright lights of Manhattan to the grand estates of Long Island’s Gold Coast, prepare to be immersed in the glamour and opulence of the Jazz Age.

Day 1: Get ready for an unforgettable tour of Long Island’s historic Gold Coast. This morning we’ll travel to New London, Connecticut to board the ferry to Long Island’s North Fork. Upon our arrival, we’ll make the short drive to the Village of Greenport for a waterfront luncheon. After lunch, enroute to our hotel in Riverhead, we’ll celebrate the 100^th anniversary with a wine tasting at Raphael’s Winery. (L) 

Day 2: This morning we’re off to Long Island’s exclusive area of Southampton, known for its beaches, art, history and luxury. Sit back and relax as our enthusiastic step-on guide provides a narrated tour of historic neighborhoods, the famous Cooper’s Beach and Billionaire’s Row – the most expensive stretch of real estate in the Hamptons, where the average property value is well over $25 million! Following the tour, we’ll enjoy free time for lunch and shopping in the historic village of Sag Harbor.

This evening, we’ll indulge in an early dinner and live entertainment at Swing 46, a jazz and supper club located in NYC’s historic Restaurant Row. After dessert, we’ll make our way to the Broadway Theatre for the 7:00 pm performance of The Great Gatsby. We’ll be transported into the opulent world of the 1920s for the story of Jay Gatsby, a self-made millionaire, and his pursuit of Daisy Buchanon, a wealthy young woman whom he loved in his youth. (B,D)     

Day 3: After breakfast (incl.), step back into the Gilded Age and the Roaring ‘20s for a glimpse into the elegant and lavish lives of the elite immortalized by The Great Gatsby. Our first stop is at Old Westbury House and Gardens. Known as one of the grandest Gold Coast Mansions, this elegant estate features a 23-room English manor home furnished with priceless antiques and grounds that include sweeping lawns, wooded paths and some of the most beautiful formal gardens in the world. A leisurely picnic lunch will be served on these beautiful grounds.  Following lunch, we’ll embark on a 2-hour Gatsby-themed boat tour of the “courtesy bay” separating the “enormous eggs” which served as Fitzgerald’s setting. We’ll envision where Gatsby’s mansion might have stood and imagine him gazing at the green light on Daisy’s dock.

This evening, we’ll stay at the stunning Oheka Castle. Believed to have been the main inspiration for Gatsby’s mansion, this 109,000 square foot French-style chateau was one of the most luxurious on Long Island and the site of the hottest parties on the East Coast. The “who’s who” of high society, international politicians and, of course, famous Hollywood movie stars were regularly spotted at the residence. This evening is yours to experience the golden age of the 1920s on this magnificent property. (B,L)   

Day 4: The leisurely morning begins with an exquisite breakfast with impeccable service. Later, we’ll experience what it was like to live in a home of this magnitude as we take a 60-minute tour of the property. Following the Castle tour, it’s back to reality as we return to the ferry and head home with wonderful memories of our Great Gatsby Gold Coast tour. (B)

Don't miss this tour, Old Sport!

To make a reservation:

Simply click here for the reservation form then complete and submit. (Payments should be received no later than 5 days after reservation has been confirmed).

Space is limited and reservations are accepted on a first come – first served basis. Questions? Call Sharon Patton at 508.828.5305 or send an email to: [email protected]

Convenient departures from Attleboro, Franklin, New Bedford and Taunton (a minimum of 10 people is required for location pick-up).

In the event that it becomes necessary to cancel your reservation we will make every effort to grant a full refund provided notification is received at least 21 days prior to the event. In some situations, certain non-refundable charges may be deducted from the amount of the refund.

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