Our Trip to New York City

The Importance of Leisure

In the current climate its easy to get super focussed on work, savings, investing and the stock market. I would be the first one to tell you that I fall into this trap from time to time and it brings its own kind of risk. To draw a parallel to losing weight if you give up all the bad foods entirely it is very easy for the temptation to build and build and build then bam there goes the diet. Same thing with investing if you focus on saving in every little area, without taking small enjoyments, this could drive you towards a big reckless purchase.

Another thing to think about is quality of life. While I do really enjoy staying plugged in all the time and watching the numbers go up, almost like building a character on an MMORPG, unplugging and enjoying the finer things (in moderation) is invigorating. Luckily for me I have my wife to remind me of this and this year we decided to go big with a 5 day trip to New York. Neither of us had ever been and outside of our wedding in 2023 we have been pretty focussed on saving these last few years. Before booking the trip we did some research at first to familiarize ourselves with the different areas and then asked our friends and family for those must see spots in their eyes. After a month or so of consideration (at one point I was debating driving down to save on air fare) we landed on 5 days and four nights. We chose our hotel location to be somewhere between Central Park and Times Square for pure convenience purposes. Luckily for us the travel market was full of great deals this summer and we managed to secure a hotel and flights from Toronto to NYC for a very reasonable $3400. Just for fun I looked at what the parking at that hotel was like and it turns out it was over $100 a day (CAD) and once we got there I’m glad I didn’t drive.

The Trip

Day 1

First day of the trip we arrive at Pearson Airport in Toronto so early in fact that we can’t even get to our gate. We had a good laugh as that paints the perfect picture of us always being at least on time if not wildly early. Our flight was Air Canada in a smallish plane with only two seats aside. It was an newer model with a telescopic head rest that was appreciated by my taller frame. After a quick flight and a mimosa we landed at LaGuardia Airport. Thankfully we each took a reasonably sized duffel bag and did not need to check any bags. (sidenote: I still can’t believe how much stuff, the size of bags people try to carry on and how they get upset when forced to check it.) Leaving the airport was very smooth we chose to opt for the paid bus as the free bus line was miles long and we set out for a subway connection to the city.

Luckily parts of the train / subway were above ground and we had some great views on the way to the heart of the city. We arrived at our hotel around noon a good 4 hours before our check-in time but luckily our room was ready. A quick refresh and we were off to Times Square which was pretty impressive I have to say like a Yonge-Dundas Square on steroids. After a quick bite (New York Hotdog #1) we headed down to visit the Toronto Public library and take in some of the sites before heading up the Empire State Building (standard edition). I’ll have to say we sure did have a beautiful day to do that on.

To wind out the day we went out for dinner in the Flat Iron Building to Eataly at Pizza and Pasta.

Day 2

The second day of the trip was an extremely ambitious one for us I walked 26,000 steps and my partner walked 29,000 steps. We did basically the same amount of walking but there is an almost full foot height difference so as my wife would say short people problems. To achieve all of those steps we walked the Brooklyn Bridge around DUMBO, then back to Manhattan on the Manhattan bridge.

Once getting back to Manhattan we walked through Little Italy where there was a huge food festival going on and we had some pizza. Definitely not New York style so we ended up ordering a New York Style pizza later on in the day for dinner!

Post dinner was the absolutely incredible showing of Back to the Future the Musical which I absolutely loved. Roger Bart had almost anime like expressions while playing Doc Brown, Evan Smith as George McFly looked like a clone right out of the movies and last but certainly not least Casey Likes pulled off an amazing performance as Marty McFly. We managed to score front row seats which were great at the Winter Garden Theatre.

Day 3

After a very busy Day 2 we chose a more low key day two and escaped to Roosevelt Island. We chose to subway most of the way there and take the Tramway over the water. It gave us a very nice view of the island and was a pretty quick trip. We walked around the Island drinking our coffee and took everything in. It was at this point we talked about how this is quite the opportunity that we have and we shouldn’t waste it as who knows what the future will bring.

Next we visited Central Park and I couldn’t believe it they were hosting a Pickle Ball tournament right there in park. It’s wild to think how big that sport has become, we watched part of the match between the Brooklyn Aces and the Florida Smash.

Post central park we visited the city within a city also known as the Rockefeller Centre! Again we went with the standard tickets as they were more than enough. I really enjoyed that they showed you a short video explaining some of the history ahead of time and after that we visited the Top of the Rock! Here I managed to take this picture framing the Empire state building and an ity bitty Statue of Liberty way in the background.

To round out our Day 3 in the city we attended the longest running play titled, “The Perfect Crime”. The main actor Catherine Russel has performed in all but 4 of all the shows since 1987. She even has a Guinness Book of World Records entry for that feat. Post show we spent a couple hours in Times Square

Day 4

Wall Street baby! As someone who has spent an incredible amount of time since 2018 thinking about stocks and the stock market this was huge for me. We started off by waiting outside the Bull and yes we waited for both ends. After that we walked down to the New York Stock Exchange. Although we didn’t spend a ton of time down there it felt great to see where it all began.

We then headed for the Staten Island Ferry terminal. As it wasn’t too far we chose to walk, unfortunately this was the first overcast day of the trip but hey you win some you lose some. Upon arriving at the terminal we were swarmed by sales people trying to up-sell trips around the bay. This was something we chatted about before but decided this would be one area we would skip and save some money. Instead we chose the free Staten Island Ferry and settled for a quick passing of the statue both ways. One funny thing is about half of the people got off the ferry and immediately started running to the other side catch the ferry back. We were not in that group.

Post Staten Island we chose to make our way north along the west side of the island stopping at the World Trade Centre, Friends Building, Chelsea Market, and we walked the highline.

We rounded out our day going out for dinner at the famous Tony’s Di Napolis restaurant. This was recommended to us from a few friends and it definitely did not disappoint. Their portions were huge and everything is family style. Only thing I wish was that we had more people with us so that we could have ordered more dishes.

Day 5

Alas the final day of our trip was here, our checkout time was noon so we took in a few more sights and headed to Ellen’s Starlight Diner. The premise of this restaurant is that all of the servers are trying to become fulltime performers on Broadway so they take turns singing as you enjoy your meal. If it sounds a bit much I didn’t find it that way at all, they even had a decibel gauge on the wall and you could tell the DJ was keeping it in an enjoyable range. When asking my wife about this place she said I wish I could eat breakfast there everyday!

After checking out of the hotel we went up to Central Park to relax for a few hours and we did this by the “Friends Fountain”. I’m sure you’ve seen this one before it is the one that is used in the opening credits

Breakdown

Now since this is a financial blog we have to dig into the cost. I have laid out the higher ticket items and included visa point rebates.

Price (CAD)	Description
$3,400	Flight and hotel as a package
$525	Back to the Future on Broadway
$100	The perfect crime off Broadway
$150	2 Tickets up the Empire State Building
$140	2 Tickets up the Rockefeller Centre
$178	Tony’s Di Napoli
$218	Eataly
$989	Food, Travel and Entertainment
$5,700	Subtotal
-$1,310	Visa Points Rebate
$4,390	Out of Pocket

All in all I think for a trip to New York, when the exchange rate is close to 1.4 CAD for ever $1 USD, we did pretty well. We did do a few things to help with the costs like:

• Going to a Target to buy snacks / water
• Buying a Large Pizza night 3 and ate it for lunch on Day 4
• Only had 1 alcoholic beverage with each meal if at all
• Using our hotels breakfast credit every day (aside from the final day that we did not get a credit for)

My final thoughts on a New York trip is it’s bigger than you think, everything is wildly expensive think Toronto prices but its USD and if you are trying to do a trip on a budget NYC is probably not the place for you!