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A New York Minute: Jess Dover's Five Night New York City Itinerary

8th July 2024

The Big Apple, the city that never sleeps, the centre of culture, style and entertainment – New York City has it all. But for a first-time visitor, where do you start?


Australian luxury influencer Jess Dover recently went on a one of a kind trip to New York City with Travel Associates. Here's an exclusive look at everything Jess and her best friend, Lili, experienced during their unforgettable girls' trip to New York, planned by one of our expert travel advisors.


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Awaiting to experience Air Canada's Signature Class to New York City (Via Vancouver)
Awaiting to experience Air Canada's Signature Class to New York City (Via Vancouver).


Arriving in Style

To kick off her one of a kind trip, Jess opted to fly in style with Air Canada’s Signature Class. Departing from Sydney, she arrived in NYC after a brief layover in Vancouver, a total journey time of 22 hours. Our Travel Associates advisors recommend Air Canada, United, Qantas and Air New Zealand for the fastest and most direct routes from Australia and New Zealand, to New York City.


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 Jess and Lili stayed at NYC's most iconic address: The Plaza.
Jess and Lili stayed at NYC's most iconic address: The Plaza.


One of a Kind Accommodation

For a New York City experience, it doesn’t get more iconic than a stay at The Plaza. On the recommendation of our luxury Travel Advisor, Jess checked into a Deluxe King Room at this legendary hotel, which has been hosting illustrious guests since 1907.

Located on 5th Avenue at Central Park, The Plaza was the perfect base for Jess and Lili to explore Manhattan’s best shopping destinations and cultural landmarks like the Museum of Modern Art (MoMA), Broadway, and the Rockefeller Center.


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Jess and Lili at Central Park.
Jess and Lili at Central Park.


Day One: Classic NYC

After a restful night’s sleep and delicious breakfast at The Plaza, Jess was ready to sightsee and tick off as many New York City landmarks as possible on her first 24 hours in NYC. Our advisors recommend a private day tour as one of the best ways to achieve this (especially if you are time-poor), with an expert guide adding to the experience by sharing stories and the history behind the popular NYC landmarks.

Some key sights to tick off include Wall Street, Times Square, Central Park, Empire State Building, Grand Central Terminal, 9/11 Memorial, and Wall Street.

The day concluded with an exquisite dinner at Manhatta, a luxurious restaurant located on the 60th floor of a Financial District tower, offering fine dining cuisine and incredible views over Manhattan.


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Catching a game at Yankee Stadium is a NYC must
Catching a game at Yankee Stadium is a NYC must.


Day Two: Exploring the Boroughs

New York City is spread across five diverse boroughs: Manhattan, Brooklyn, Queens, The Bronx, and Staten Island. Because the city is so vast, our advisors recommend picking a borough or two to explore as an excellent and efficient way of seeing the city.

Jess spent her second NYC morning strolling through Central Park and enjoying a bagel picnic before getting the subway to the Bronx to watch the New York Yankees take on the Dodgers at the Yankee Stadium. It doesn't get more 'New York' than a Yankees game - and the hot dogs, merch, and electric atmosphere was one of Jess’ favourite parts of her New York trip.


Day Three: Shop Til You Drop

New York City is a fashionista’s dream, and Jess and Lili knew they wanted to indulge in some retail therapy during their trip. Our advisors' shared their top shopping spots and designer hidden gems for Jess and Lili, starting on 5th Avenue and making their way down to Soho and Nolita, neighbourhoods known for their trendy boutiques and emerging designers.

Lunch at one of the area's renowned restaurants (our advisor’s recommend hotspots like Le Coucou, Balthazar, or Carbone) provided a delicious break from shopping.

Travel Associates' hand-picked evening activity for Jess and Lili was to attend award-winning Broadway show, Hamilton - a New York must.


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Jess took her trip to new heights with a helicopter tour over NYC.
Jess took her trip to new heights with a helicopter tour over NYC.


Day Four: Culture and Views

On her final full day in New York City, Jess started with a private tour of the Museum of Modern Art, enjoying exclusive access before it opened to the public. This unique experience, organised by Travel Associates, allowed her to admire some of the world’s finest art pieces in private.

Next, Jess picked Brooklyn as the next NYC borough to explore, stopping by DUMBO and admiring the streets with beautiful brownstone buildings. She visited 1 Hotel Brooklyn and headed to the rooftop bar, Harriet’s, for stunning views of the Manhattan skyline.

Jess opted for the perfect NYC send off: a spectacular helicopter tour over New York City. Departing from New Jersey, this private 30-minute flight offered unparalleled views of the city’s iconic landmarks, providing a fittingly grand finale to her luxurious adventure.


To experience this one of a kind NYC adventure for yourself, speak to your luxury travel advisor or read more about this itinerary here.