My New York Itinerary

2 Days in the big apple…

One of the first times I ever visited New York City was when I was a snot-nosed kid hanging out in Brooklyn. I took my cousins bike out for a ride, got jacked and got the bike stolen. That was my first taste of the big apple. Well, since then I’ve grown up a bit, got a little wiser, got a little tougher, I started a travel blog and I still have and love my family out in Brooklyn. Courtesy of the As You Stay app I’ve been invited to stay in Manhattan for a couple of days, shacked up in the very cool hotel called Row NYC formerly the Milford New York. While there, I put together this 48 hour New York itinerary.

Day 1

Central Park + John Lennon (The Dakota, Strawberry Fields, Imagine Mosaic), Bethesda

Spreading across 843 acres of land, Central Park is New York City’s greenest, natural setting. The massive park offers all sorts of attractions such as: Strawberry Fields, which is a magnificent 2.5-acre section of Central Park that is dedicated to the late musician and peace activist John Lennon; the world famous Great Lawn; the Bethesda Fountain, which is one of New York City’s largest and most iconic fountains, and many other famous sights.

5th Ave

Considered to be one of the world’s priciest shopping streets, 5th Avenue is one of New York City’s main shopping destinations. 5th Avenue runs for 6.2 miles starting at Washington Square Park and ending at 142nd Street in Harlem. Along 5th Avenue, you will find famous high-end retail stores such as Tiffany and Co., Louis Vuitton, Takashiyama, Fendi, and many other well-known retail stores.

Rockefeller Center | Top Of The Rock

100 years ago John D. Rockefeller Jr., of the prominent Rockefeller family, envisioned a facility in Manhattan that would be “city within a city”. Rockefeller Jr.’s vision became a reality in 1930 when construction of the Rockefeller Center began. By 1939, the Rockefeller Center was completed and to this day, Rockefeller Center is one of New York’s main hubs of extraordinary art, panache, and entertainment.

The Empire State Building

This famous 102-story skyscraper is located in midtown Manhattan between West 33rd Street and West 34th Street. It has two observational decks: the first on the 86th floor and the second on the 102nd floor. Not only is it an American cultural icon, the Empire State Building also serves as an office space for companies such as LinkedIn, Walgreen, and Bank of America. Did you know that the Empire State buildings come from New York’s nickname, the Empire State?

Radio City Music Hall

Nicknamed “the Showplace of the Nation”, Radio City Music Hall is the main entertainment venue of the Rockefeller Center. With 85 years to its name, Radio City Music Hall has been used for concerts, the world-famous Radio City Christmas Spectacular, Cirque du Soleil: Zarkana, television shows, and sporting events such as a New York Liberty basketball game, the 2000 Roy Jones Jr. boxing match against David Telesco, and the NFL Drafts from 2006-2014.

Grand Central Terminal

Dubbed “the busiest train station in the United States”, Grand Central Station welcomes over millions of visitors a year and embodies New York’s “restless and innovative energy”. This 150-year-old terminal is one of the world’s most famous attractions and serves as the main junction for train transportation to outer-city New York counties and to the state of Connecticut.

In this video, we show you day one of our 48 Hour New York Itinerary

Day 2 (Option 1)

48 Hour New York Itinerary

The High Line + Bubby’s High Line

Created in 2009, the High Line, also known as High Line Park, is a 1.45-mile long elevated outdoor promenade running along the Lower West Side of Manhattan. This outdoor promenade offers some of the best views of the Lower West Side of Manhattan, as well as beautiful foliage, an urban theatre, and neat benches to relax and enjoy a nice New York day City day!
Bubby’s is a New York City institution known for its solid American comfort food, especially the eggs, pancakes, and fried chicken served at brunch every day of the week.

The Whitney Museum

The innovative Whitney Museum is home to a wide variety of twentieth-century and contemporary American art, with a concentration on works from living artists. This unique and contemporary museum is believed to have the world’s finest collection of twentieth-century American art.

Washington Square Park

Washington Square Park is one of New York City’s most famous public parks. The 9.5-acre park welcomes visitors with its iconic Square Arch, located at the park’s northern entrance. Aside from the Washington Square Arch, Washington Square Park has an equally iconic fountain that is located in the center of the always-busy park.


Flatiron Building

Designed by Chicago architect Daniel Burnham, this beloved New York City building has captivated the hearts and cameras of people all over the world. This 22-story New York City icon is located on 5th Avenue between West 22nd and West 23rd Street in Manhattan.

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Times Square

If there’s one part of Manhattan that comes to minds of every tourist and local, more than likely it’s Times Square. Sometimes referred to as “the Center of The Universe”, Times Square is one of the busiest intersections for commerce, entertainment, and tourism. The bright lights of the billboards and the restless spirit epitomize the soul of New York City- the city that never sleeps.

Times Square is also near the theatre district famous for Broadway shows and off-Broadway shows. You won’t be able to fit a Broadway show into your New York Itinerary but it checking out musicals in NYC is a definite must!


In this video, we show you day two of our 48 Hour New York Itinerary

Day 2 (Option 2)

48 Hour New York Itinerary

World Trade Center & Memorial Site

One World Trade Center, also known as the Freedom Tower, is the main structure of the World Trade Center complex. Standing at 1,792 feet tall, the Freedom Tower is the tallest building in the Western Hemisphere and the sixth-tallest building in the world. While this building is an architectural feat, it must not be forgotten that the Freedom Tower and the memorial site stand as commemorative edifices for the events that took place on September 11, 2001.

Statue of Liberty

Designed by French sculptor Frederic Bartholdi, French engineer Gustave Eiffel (the architect of the Eiffel Tower), and American architect Richard Morris, the Statue of Liberty is one of the world’s most monuments. The Statue of Liberty, formerly known as Liberty Enlightening the World, was completed in 1884 but wasn’t dedicated to Ellis Island until 1886, as a gift from France to America in honor of their alliance during the American Revolution.

Wall St., Charging Bull

Home to the New York Stock Exchange, NASDAQS, and the famous Charging Bull, Wall Street is one of the world’s epicenters of commerce. This originally Dutch-owned territory has always served as an industrious marketplace for businesses from all over the world. Did you know that Wall Street is believed to have gotten its name from a wall built by the Dutch in order to keep out Native Americans, the British, and pirates?

China Town

When it comes to the best Chinatown in America, New York City’s Chinatown takes the cake. Chinatown combines all aspects of Chinese ethnicity with the gritty pace and cultural diversity of New York City. Chinatown borders four NYC neighborhoods: Tribeca to the west, the Lower East Side to the East, Little Italy to the north, and the Civic Center to the south.

Brooklyn Bridge

The Brooklyn Bridge connects Brooklyn and Manhattan from Adams Street in Brooklyn to the City Hall area in Manhattan. Its open-air promenade offers one of the best panoramic views of New York City.

In this video, we show you day two of our 48 Hour New York Itinerary


The Row NYC is located in the Theater District and is within a 3 minutes’ walk of Times Square. The hotel features a fitness centre, concierge service and a business centre. The Rockefeller Center is also a short walking distance away.

Booking Flights:


The average person doesn’t need to think twice about getting out of town for a 48-hour travel adventure or a long weekend. The only thing stopping you dead in your tracks is finding cheap flights. Please visit our helpful posts on Booking Flights. Personally, I’m all about simplicity so I recommend Skyscanner, the best way to search the best rates in flights.


Now that you have an idea of some of the main things to see be sure to the read about The 6 biggest mistakes tourists make when visiting New York City (and what to do instead).
New York, New York is the one city that I can honestly say I love as much as Toronto. It’s about a one hour and twenty minutes direct flight from Billy Bishop Toronto Island Airport YTZ to Newark Liberty International Airport EWR via Porter. With Porter offering frequent flights I can literally put New York City in my own backyard. We’ve officially made a trip to NYC our annual Easter Long weekend getaway destination. That guarantees at least one visit a year but with so much more to see and do plus 4 other boroughs to explore we may have to already start bumping up our visits.


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About Me:
Using the latest travel apps, technology, and gear, I take a city; see the sights, taste the food, smell the roses, hear the stories and feel the love. All in 48 hours. Then, using videography & editing, photography and writing I retell and share those stories with my readers and viewers.

I'm Christopher Rudder and welcome to Rudderless Travel.

Read more about me here: Being Rudderless With Christopher Rudder
here Rudderless Travel gets nominated for the Leibster Award
and here: A Consultant for Special Needs Students, AND a Travel Blogger!

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All opinions belong solely to the blog unless otherwise mentioned and never influenced by a third party ’cause that's how we fly.

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