Admiring the sunset from the One World Observatory

After quitting my job of 8 years, I had some time before my new job started, so I decided to book a trip. New York City and Boston are two places I’ve always wanted to visit and at only about an hour away by airplane, visiting them was a no-brainer. I decided to visit both of them in one trip since they’re relatively close to each other.

Once again I booked my flight through PC Travel. I was trying my best to avoid WestJet after my last poor experience, but ended up booking my initial flight to New York City with them. Shortly after booking my flight, news broke of a possible pilot strike. WestJet once again dropped the ball. It offered airline passengers refunds if flights were cancelled due to the strike. However, it would be quite costly for me to book another flight on such short notice. This caused me a lot of anxiety leading up to my trip. The pilot strike never happened and my flight was on time, but still, this isn’t a fun experience as a passenger to go through.

Booking my flight to New York City was a little confusing. New York has three main airport: LaGuardia, JFK and  Newark Liberty (across the river in New Jersey). I ended up choosing a flight that landed in LaGuardia, since there were a limited number of flights to JFK and I didn’t feel like commuting in from New Jersey.

Day 1: Saturday, June 2

The Brooklyn Bridge

I landed in New York on a sunny Saturday morning. After I grabbed my luggage, I tried to figure out how to get from the airport to my Airbnb. Luckily, the airport staff were friendly and helped me figure out the best route there. I bought a 7-day unlimited transit pass for $32, a pretty good deal, I might add. (Side note: New York is known for its yellow cabs, but I didn’t end up using one the whole time I was there since the subway system is so good.)

Although the New York subway system has the most stations in the world, for some reason there isn’t a subway station at the airport, so after a 20 minute bus ride from the airport, I found myself at the subway. New York is known for its pizza, so after grabbing a quick bite to eat, I tried to navigate my way through the subway system. I found the subway confusing at first. There were local and express trains. I had no idea which one I should board. I ended up boarding a local train since I didn’t want to miss my stop.

As the name suggests, express trains only stop at select (main) subway stations. On the official New York City subway map, the express stops have a white circle, while local stops have a black circle. If the stop you want to get off at has a black circle, don’t get on an express train, otherwise you’ll miss your station.

I used Google Map to figure out the best route to get me to my Airbnb. The problem was that Google Map didn’t take transit fares into account. It advised me to take the Long Island Rail Road, however, I found out that wasn’t covered by my transit pass, so I planned a new route. After struggling for 45 minutes, I finally figured out the train I was supposed to board and made my way to my Airbnb.

When I was staying in New York, I wanted the “real” New York experience, so I decided to stay in Brooklyn. When I arrived in the neighbourhood, it seemed a little sketchy. There were people loitering on the streets and the buildings were rundown and covered with graffiti. To say I was a little intimidated would be an understatement. To make matters worse, when I arrived at the building I was supposed to be staying at, I couldn’t figure out my unit number. When I entered the building, there was loud music playing and the hallway was dark. I didn’t know whether my unit was on the ground floor or upstairs. (It didn’t help that the unit number was missing on the place I was supposed to stay.) The host wasn’t there and I didn’t feel comfortable entering the unit I thought I was supposed to be staying at (accidentally entering someone else’s place in Brooklyn probably isn’t a good idea), so I left the building and decided to explore Lower Manhattan. When I exited the subway station in Manhattan, I was awestruck. I didn’t know where I was going, so I ended up walking along Broadway for a while.

Eventually I found myself at the Brooklyn Bridge. The Brooklyn Bridge is a must-visit New York City attraction. It’s a hybrid cable-stayed/suspension bridge spanning the East River that connects Manhattan and Brooklyn. Completed in 1883, it’s one of the oldest roadway bridges in the U.S. The weather was gorgeous, so I walked across the pedestrian walkway. It offered a breathtaking view of the New York City skyline.

By this time it was getting late and I still hadn’t heard from my Airbnb host, so I was getting worried. I didn’t feel like sleeping on the streets of New York, so I started thinking about finding a hostel or hotel to stay at. Finally, I was able to reach my Airbnb host on WhatsApp and figured out the unit I was supposed to be staying in. I was tired of lugging around my heavy luggage in Manhattan, so I headed back to Brooklyn, unpacked and called it an early night.

Day 2: Sunday, June 3

On top of the same building King Kong scaled, the Empire State Building

I had limited time in New York and wanted to make sure I saw all the major sights, so I booked a 3 day hop on hop off bus tour with CitySightSeeingNY. I went with the FreeStyle Pass, which also included my choice of 3, 5 or 7 attractions. I went with 5 attractions. By doing this, I was able to save 40% or more versus walk-in ticket prices at attractions. The sightseeing bus was a great way to see New York. Not only did I save time, I also saved money versus taking a cab everywhere.

There were several bus tours, but I decided to start with the downtown one. The tour started at Times Square. Times Square was impressive. It reminded me of Dundas Square in Toronto, but on a larger scale. It was neat seeing the ball that was lowered to bring in 2018. After driving by some impressive sights, including Penn Station, the Flatiron Building and Madison Square Garden, I got off at my first stop, the Empire State Building.

The inside of the Empire State Building is as impressive as the view from up top. Learning about the construction and history of the building was fascinating. Even though it’s no longer the tallest building in New York, the Empire State Building still gives you a beautiful view of the skyline.

Since I was in the neighbourhood, I also stopped in at Macy’s, formerly the world’s largest department store. I rode the wooden escalators and played the FAO Schwarz piano just like Tom Hanks in the movie, “Big.”

It was another gorgeous day, so in the afternoon I decided to explore Central Park. I knew Central Park was big, but I didn’t realize just how big it truly was. Apparently, there’s a zoo there and waterfalls. I came across some of the water falls, saw the model boat sailing and walked along Jacqueline Kennedy Onassis Reservoir, but never made it to the zoo. (Maybe next time.) I walked from one end of Central Park to the other from south to north. It took about two hours. After that I was pretty tired, so I called it a day.

Day 3: Monday, June 4

The Law & Order courthouse building at 60 Centre Street

It was already my third day in the Big Apple and I hadn’t seen any of the sights from my favourite TV show, “Law & Order.” That had to change, so I looked up the address of the iconic Law & Order courthouse building. The building is called the New York County Courthouse and it’s located at 60 Centre Street. I remember walking around the corner and instantly recognizing the building I’d seen so many times on TV. It had the inscription, “The True Administration of Justice is the Firmest Pillar of Good Government,” a quotation taken from a letter written by George Washington. Walking the same steps as my favourite Law & Order character Jack McCoy was surreal.

After exploring Chinatown and walking across the Manhattan Bridge, I spent the afternoon at the Museum Of Modern Art‎ (MoMA). Now, I’m not someone who considers myself artsy, but I still had an fun time there. (I probably would have had a better time if I took the time to listen to the stories from the actual artists.) You can literally spend all day at the museum, but I decided to call it quits after two hours, since I had other things to see.

I spent the rest of the day exploring Lower Manhattan. I visited Wall Street’s Charging Bull (and in case you’re wondering, no, I didn’t touch its balls for good luck), walked along Wall Street and saw the New York Stock Exchange.

The whole time I was in Lower Manhattan I could see an impressive glass structure towering over all the other buildings, so in the evening, I visited One World Trade Center, America’s tallest building, and took in the panoramic view  from the One World Observatory. The views were absolutely stunning. I could see the Brooklyn Bridge, the Statue of Liberty, the East River and the Hudson River. The sun just happened to be setting, giving me an even more impressive view. It was the perfect way to cap off a pretty amazing day.

Day 4: Tuesday, June 5

National September 11 Memorial

On my last full day in the New York City, I visited the National September 11 Memorial & Museum. Anyone visiting New York City should make sure to stop by there. Seeing the fountains where the World Trade Centre once stood was surreal. Seeing all the names of the victims inscribed with flowers laying on top of their names was touching and almost brought a tear to my eye. The museum was equally touching. Hearing the stories of the victims and the heroism shown by firefighters, police and citizens was moving. You’re not permitted to take photos in the exhibits, so you’ll just have to visit it yourself in person and see.

In the afternoon, I visited all the places I hadn’t yet been to. I went to High Line Park, a 1.45-mile-long elevated linear park, greenway and rail trail. Located in the west side of Manhattan, it was created on a former New York Central Railroad spur. I can’t say I’ve ever been to a park like this. It’s a little off the beaten path, but well worth the visit. After that I went to the New York Public Library Main Branch (from the movie “Ghostbusters”) and Grand Central Terminal. (Side note: nobody seems to follow the rules of the road in Manhattan, pedestrians included, who jaywalk on red lights.)

I had one attraction left from my FreeStyle Pass, so I finished off my time in New York City by visiting the Rockefeller Center. The Top of the Rock Observation Deck gave a breathtaking 360° view of New York City. You almost feel like you’re skydiving. All that’s separating you from falling are some clear glass window panes.

After that I headed back to my Airbnb to pack up for part 2 of my trip in Boston.

Sean Cooper is the bestselling author of the book, Burn Your Mortgage: The Simple, Powerful Path to Financial Freedom for Canadians, available now on Amazon and at Chapters, Indigo and major bookstores, and as an Audiobook on Amazon, Audible and iTunes.