Traveling Hacking New York City

Trump Tower – Anyone ever read the Dark Tower series?

This title might be a little misleading. In reality, we did utilize credit card reward points to minimize the costs of our trip to New York City, but all of the points used were accumulated during the push to travel hack the Disney World trip  we took last October.

This was our first trip to New York City. The town has a reputation of being fun, exciting and maybe a little dangerous. I was looking forward to seeing something memorable. Instead, the trip was a little dull.

I never once witnessed the quintessential rudeness of New Yorkers (well, maybe once, but he was a personal friend). Not once did someone pound on the hood of a car and yell, “I’m walking here!” There were no bodies floating in the East River. The Statue of Liberty was not the site of a terrorist attack. Only pasty tired-looking people trod past, eager to find a ray of sunlight on one of the many trendy café sidewalk patios. No one even tried to mug us.

The only excitement was at a park one afternoon when two little 5-year old assholes were mowing down other unsuspecting children with their bikes.

Dull.

“Rockefeller Square – Meh. Is this a highlight? I can’t tell.”

But, to be fair, we really went to visit my cousin and that was all good. Except that everyone was sick and then we got sick. Oh well. Can’t win them all.

 

New York City trip expenses

We spent $1,942 for a 7-day/ 6-night trip over spring break. We could have spent less if I would have hustled some more credit card points, but truth be told, I just couldn’t be bothered this time.

Frankly, I feel pretty good about scoring free flights and discounted hotel stays. We saved an estimated $1,888!

 

Here’s the breakdown:

Our highest costs were accommodation, food and pet sitter.

Lodging. The main impetus for visiting New York was to visit my cousin and his family. They live in a trendy part of Brooklyn called Greenpoint and we chose a boutique hotel near their house. Originally, I had applied for the Chase Reserve card that was offering 100,000 ultimate reward point plus a nice travel credit. This would have taken care of all our lodging costs. However, both Mr. TJL and I were denied. Plan fail.

Instead, I used $577 in fixed-value points acquired from a Barclay Arrival + card to lessen the expensive lodging costs. In total, the hotel cost us just over $1,000.

 

Food. We did pretty good here. We hit the grocery store and ate breakfast in our room everyday as well as a few dinners. We also ate dinner at my cousin’s house a couple of times. All other food was consumed at restaurants, but we managed to keep our costs pretty low.

 

Pet Sitter. Usually my sister would watch the house and dogs for free but she couldn’t manage it this time. We ended up scrambling a bit, but found someone who did a great job with the dogs.

 

Big Wins

 The biggest wins on this trip were free flights and airport parking.

I had 62,615 Ultimate Reward points through Chase available for airfare for three people. Through the Chase portal those flights would have cost us 75,000 points, however after checking Southwest, I found non-stop, round-trip airfare for only 48,174 points. I transferred my UR points from Chase to Southwest and purchased those cheap tickets! Not only did we score free flights, we paid zero dollars for checked baggage (the first two bags are free!).

Southwest is a little weird in their boarding scheme as they have no assigned seats. I was nervous about not finding a seat next to my child so we jumped ahead in line with family boarding. Yep, we cheated a little but seriously parents should be seated with their minor children.

Airport parking usually costs us around $100 in long-term parking lots. However, this time the hotel (Aloft Hotel- Denver International Airport) that we stayed with prior to the flight offered us $5 per day parking. In the end they only charged us $20; I like their math!

 

 Missed Opportunities

Lodging could have been way cheaper if we would have booked with Airbnb. My initial searches found lodging for between $100 – $150 per night. The total cost could have been almost entirely eliminated by the Barclay Arrival+ card points. However, every time I tried to book an apartment, I would get stalled halfway through the process. I know it sounds dumb, but I couldn’t figure out how to complete a booking through Airbnb. Finally, I got impatient and booked the easy hotel instead. My impatience cost me.

Additionally, we could have cut our transportation costs by using a first time promotional code for Uber. I found one for $35 dollars off. By signing up with Uber for myself and Mr. TJL, our transportation to and from the airport could have been free. The only thing that stopped me was that I was a bit nervous about using Uber. I have never used the service, I don’t understand how you know which ride is yours, where they pick you up, etc. Again, my lack of know-how and experience stopped me.

 

Have any of you ever had problems booking with Airbnb or Uber? Sometimes stuff like this just makes me feel old.

 

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6 Responses to Traveling Hacking New York City

  1. Marc says:

    Inspiring! Especially after you outline how you could have done it for even less. Sorry you didn’t have as much fun as you’d hoped, but I’ll bet it’ll still prove to be a memorable trip.

    • ska@thejollyledger.com says:

      It was fun enough just not as harrowing as I would have liked. You know how I like to spin the tales of my experiences! NYC gave me nothing to work with.

  2. It looks like you managed to make the most of your spending despite the few areas where you may have saved a few bucks. We don’t trust services like Uber either and always thought is was because we were older. We still can’t get our heads around the fact that one day all cars will be self driving!

    • ska@thejollyledger.com says:

      Someday I will get up the nerve to try Uber. Truth be told I like to be walked through these sorts of things. Maybe I can find a savy urban friend someday.

  3. K says:

    I’ve used Uber many, many times. They’ve been a life saver for me as I recover from as medical condition that prohibits me from driving. You get a text message in advance with your driver’s name, picture, car make/model and license plate number. I always text that to my spouse before I get in the car and confirm when I’ve reached my destination. Drivers are nice and very accommodating. Don’t be scared.

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