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Ref: A411

Follow the Great Gatsby Fly Drive

New York * The Hamptons * Newport * Cape Cod * Boston

The Great Gatsby, the1925 novel written by American author F Scott Fitzgerald follows a cast of characters living in the fictional town of West Egg on prosperous Long Island in the summer of 1922. The story primarily concerns the young and mysterious millionaire Jay Gatsby and his quixotic passion for the beautiful Daisy Buchanan. This 10-day Fly Drive will take you from the metropolis of New York to the millionaire’s playground of the Hamptons and Cape Cod.

10 days from £1,986 per person twin share + flights


Day 1 - UK - New York

Your Great Gatsby Tour begins with a scheduled Virgin Atlantic flight from London Heathrow to New York on arrival transfer independently to your hotel.

Overnights (2): New York

Day 2 - New York City

Soak in the vibrant atmosphere of the Big Apple, hunt for bargains in the fashion district or in true Gatsby fashion, head to the world-class boutiques of Madison Avenue. Be sure to visit the famed Plaza Hotel, where Gatsby resided when in Manhattan. Take a stroll through Central Park and be sure to visit one of New York’s many exceptional museums before ending your day with Dinner and a Broadway show! (optional)

Day 3 - New York – The Hamptons (92 miles)

Pick up your rental car and depart Manhattan for the North Shore of Long Island, where F. Scott Fitzgerald and his literary masterpiece were based. Visit one of the North Shore’s historic “Gold Coast” mansions, which were the inspiration for Gatsby’s seaside estate. One such inspiration is said to be Oheka Castle, which you may tour today and perhaps stop for lunch as well as it has since been transformed into a hotel and estate. After your mansion tour, continue down the Long Island Expressway toward the Hamptons, which are the modern-day home to summer estates for the New York elite.

Overnight (1): The Hamptons

Day 4 - The Hamptons – Mystic - Newport (119 miles)

After enjoying a morning walk along the beach, depart for your short interstate journey across long island sound. Heading northeast toward the tip of Long Island, board the cross-sound ferry that will take you to New London, Connecticut. On your way to Newport, be sure to take a leisurely lunch stop in historic and picturesque Mystic, perhaps at the famed pizza parlour bearing the town’s (and movie’s) name. Continue to Newport where you can arrive in time for a sunset stroll along the Wharf followed by a seaside dinner.

Overnights (2): Newport, Rhode Island

Day 5 – Newport

Spend the day in Newport touring the historic mansions of the Gilded Era that proceeded and inspired Gatsby. (optional, fees apply) These Newport estates were built by the barons of American industry in the late 19th century, the most famous being Cornelius Vanderbilt‘s The Breakers. Eleven of these mansions from a bygone era have been meticulously maintained over the years by the Preservation Society of Newport and seven of them are open to visitors daily.

Day 6 - Newport – Cape Cod (74 miles)

Depart Newport for a relatively short journey where you will quickly cross the Stateline into Massachusetts, then driving along Buzzard Bay before making the turn onto the Mid-Cape Highway, which will quickly take to you to Hyannis. One of most noteworthy summer escapes in the country, Hyannis Port is home to the Kennedy Compound, from where JFK ran his successful campaign for President in 1960 and which later became the Summer White House during his brief albeit memorable Presidency. The compound was built by Joseph Kennedy Sr., the family’s patriarch, who became very rich (some say from bootlegging) during the same interwar era as the fictional Jay Gatsby.

Overnight (1): Cape Cod / Hyannis

Day 7 - Cape Cod – Boston (71 miles)

After another beachside morning stroll, head out for another short drive north to Boston, which is one of America’s most historic and culturally important cities. While in Boston be sure to browse the boutiques of Newbury Street and crossing Boston Common toward the harbour, you cannot miss the market shops of Faneuil Hall

Overnights (2): Boston

Day 8 - Boston

Your day is free to explore Boston, the cradle of American liberty. The Revolutionary era comes to life along the Freedom Trail walking route. Visit the haunts of the patriots who stoked the fires of democracy throughout the Colonies. If you are more interested in modern history and in keeping with your previous destination, pay a visit to the JFK Presidential Library. (optional, fees apply)

Day 9 - Boston – New York - UK (215 miles)

Depart Boston for New York, where you will drop off your rental car at the airport and board your flight home.

Day 10 - Arrive UK

 2018 Departing
Twin Share
 Standard Hotels 
Triple Share
 Standard Hotels 
Twin Share
 Upgraded Hotels 
Triple Share
 Upgraded Hotels 
 May - October £POA £POA £POA £POA
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Standard HotelsUgraded Hotels
New York CitySkyline Hotel Holiday Inn New York City Midtown
Riverhead Hyatt Place Long Island East End Hyatt Place Long Island East End
Newport, RIMainstay Hotel & Conference Centre Hotel Viking
Cape CodShoreway Acres InnHoliday Inn Cape Cod - Hyannis
BostonMidtown Hotel Holiday Inn Boston-Brookline

Tour Price Includes:

  • Scheduled flights with Virgin Atlantic Airlines from Heathrow
  • Airport taxes, security charges and the Air Passenger Duty
  • 8 nights accommodation, room only
  • 9 days fully inclusive hire of an intermediate car with unlimited mileage, LDW, LIS, Sales Tax, Airport Fees, VLF and Local Surcharges
  • Long Island Gold Coast Mansion Tour
  • Mansion Tour of Newport Rhode Island
  • Detailed day-by-day itinerary, maps and directions to overnight hotels prior to your departure from the UK

Not Included:

  • Meals
  • Hotel Parking
  • Fuel for hire car
  • Ferry crossings payable locally
  • Charges apply to renters under 25 years of age
  • Entrance fees to National Parks, attractions, activities and excursions
  • Weekend flight supplements Friday- Sunday £30 each way

Our Price Guarantee

All offers are subject to availability. Once a booking is confirmed your holiday price is 100% GUARANTEED against any increase in price such as currency exchange fluctuations or fuel surcharges. Other companies may surcharge you by up to 10% more!

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Holiday Information


Skyline Hotel


Holiday Inn New York City Midtown



Hyatt Place Long Island East End


Hyatt Place Long Island East End



Mainstay Hotel & Conference Centre


Hotel Viking



Shoreway Acres Inn


Holiday Inn Cape Cod - Hyannis



Midtown Hotel


Holiday Inn Boston-Brookline